Name: EDC·HCl
Brand: Ambeed
SKU: A104599
Rating: 4.3 (153 reviews)

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1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride is a carbodiimide reagent that forms amide bonds with nucleic acids and compounds. It accelerates ester, amide, and peptide formation reactions, and is commonly used as a condensing agent and dehydrating agent in polynucleotide synthesis, hydroxylation, lactonization, and esterification.

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Machine Learning-Guided Design of High-Performance Antifungal Polymers against Candida albicans

Roh, Jooyoung ; Huang, Kang-Ting ; Choudhury, Anmol ; Quan, Tairan ; Huang, Chun-Jen ; Kumar, Priyank , et al.

DOI: 10.1021/acspolymersau.5c00057 ACS Polym. Au,2025.

Abstract: This study leverages machine learning (ML) to accelerate the development of antifungal synthetic polymers. An in-house curated data set was used to train a Random Forest binary classification model, which identified five critical features for predicting antifungal activity against the fungal pathogen Candida albicans. This model shows that antifungal polymers should contain a hydrophilic composition of at least 30%, a calculated partition coefficient (cLogP) of 0 to +0.5, hydrophobic composition limited to 20%, degree of polymerization (DP) of 18 or less, and cationic composition limited to 50% for the polymer to have an MIC₉₀ of 64 μg/mL or less. Based on these insights, a library of polymers was synthesized via reversible addition−fragmentation chain transfer (RAFT) polymerization using 2-(butylthiocarbonothioylthio)propanoic acid (BTPA) as the RAFT agent, exploring combinations of these features. A polymer exhibiting all five feature characteristics for an effective antifungal polymer presented an MIC₉₀ of 32 μg/mL-lower than the 64 μg/mL Class 1 “good” polymer threshold. After optimizing the polymer for significant antifungal activity by fulfilling the five features of the antifungal impact, we improved its biocompatibility. We did this by replacing the BTPA RAFT agent with 2-dodecyl thiocarbonothioylthio-propanoic acid (DTPA), which has a longer, more hydrophobic end-group. This modification resulted in a polymer with an MIC90 of 16 μg/mL and a hemolysis concentration (HC50 exceeding 2000 μg/mL, yielding a selectivity index greater than 125-aligning with the most competent polymer involved in the ML data set. This work validates the efficiency of ML-guided design for developing advanced antifungal polymers with enhanced potency and biocompatibility.

Keywords: machine learning ; antifungal polymer ; Candida ; random forest ; classification

Purchased from AmBeed: 25952-53-8

Synthesis and preclinical evaluation of gastrin releasing peptide receptor antagonist [18F] MeTz-PEG2-RM26 for positron emission tomography

Kanellopoulos, Panagiotis ; Lundmark, Fanny ; Abouzayed, Ayman ; Balestri, Lorenzo Jacopo Ilic ; Håkansson, Esther Olaniran ; Obeid, Karim , et al.

DOI: 10.1186/s41181-025-00336-9 EJNMMI Radiopharm. Chem.,2025,10,14.

Abstract: Background: The gastrin-releasing peptide receptor (GRPR) is overexpressed in the majority of primary prostate cancer lesions, with persistent expression in lymph nodes and bone metastases, making it a legitimate molecular target for diagnostic imaging and staging. This study presents the synthesis and preclinical evaluation of [¹⁸F]MeTz-PEG₂-RM26, a GRPR antagonist which utilises the Inverse Electron Demand Diels-Alder (IEDDA) reaction for ¹⁸F-labelling. This click-chemistry approach allows for site-specific incorporation of fluorine-18 under mild conditions, preserving the peptide's structural integrity and biological activity. Receptor specificity and affinity of [¹⁸F]MeTz-PEG₂-RM26 were evaluated in vitro using GRPR-expressing PC-3 cells. Furthermore, the biodistribution profile of [¹⁸F]MeTz-PEG₂-RM26 was assessed in NMRI mice and its tumour-targeting capability was investigated in mice bearing PC-3 xenografts. Results: The labelling of TCO-PEG₂-RM26 precursor involved three steps: (1) synthesis of an ¹⁸F-labelled activated ester on a quaternary methyl ammonium (QMA) cartridge, (2) conjugation of the labelled ester to a tetrazine amine, and (3) attachment to TCO-PEG₂-RM26 via an IEDDA click reaction. This production method of [¹⁸F] MeTz-PEG₂-RM26 afforded a high apparent molar activity of 3.5–4.3 GBq/µmol and radiochemical purity exceeding 98%, with 43–70 MBq activity incorporation, while the entire synthesis was completed within 75 min. Both in vitro and in vivo studies confirmed the specific binding of [¹⁸F]MeTz-PEG₂-RM26 to GRPR, with a significant reduction in activity uptake observed upon receptor saturation. The radioligand exhibited rapid blood clearance and minimal bone uptake, confirming the stability of the fluorine-carbon bond. However, high hepatic uptake (12–13% IA/g at 1 h postinjection) indicated predominant hepatobiliary excretion. Receptor-mediated uptake was observed in the tumours and pancreatic tissue, although the overall activity uptake in tumours was low, likely due to the rapid hepatobiliary clearance of [¹⁸F] MeTz-PEG₂-RM26. Conclusions: These findings demonstrate the effectiveness of the IEDDA click reaction for fluorine-18 labelling of GRPR-targeting PET tracers. Future studies should focus on increasing the hydrophilicity of the imaging probe to improve the targeting properties and biodistribution profile of the radioligand.

Keywords: Fluorine-18 ; TCO ; Tetrazine ; IEDDA click chemistry ; GRPR ; Bombesin ; PET ; Prostate cancer

Purchased from AmBeed: 25952-53-8 ; 403-45-2 ; 769-39-1

The Modification of Biomolecules Using Novel Diazonium Compounds and Photoactivated Systems

Ben-Zvi, Benjamin ;

Abstract: The ability to modify DNA and functionalize proteins is a foundational tool in chemical biology, essential for probing complex biological systems and for engineering new or improvedfunctions at the molecular level. Such modifications enable researchers to track, visualize, and manipulate biomolecules of interest, enabling the development of targeted therapeutics, biosensors, and diagnostic assays. Photoredox chemistry, which operates under mild conditions and leverages light to achieve high spatiotemporal control, provides a powerful and biocompatible platform for these transformations in biologically relevant settings. The use of lower energy light, such as red or near-infrared light, further enhances this approach by minimizing phototoxicity and allowing deeper tissue penetration. These features make red-shifted photocatalysis an ideal platform for bioorthogonal modifications, expanding the toolkit for probing and manipulating biological systems. Towards this goal, this dissertation describes the use of innovative photocatalytic methods to modify and functionalize biologically relevant macromolecules. The research presented here describes the use of novel diazonium compounds along with red-shifted, low-energy light to perform modifications on DNA and proteins. The development of novel photoactivatable multi-diazonium compounds led to the effective and potent degradation of DNA under mild conditions utilizing only low energy light. The potency of this method was comparable to those of its natural counterparts, such as calicheamicin. Diazonium compounds offer a synthetically more accessible mimic of natural enediyne-containing DNA cleaving agents. This method provides a more cost-effective, efficient, and modular alternative to enediynes derivatives and offers the potential for enhanced specificity through spatiotemporal control. The photoactivatable nature of diazonium compounds was also harnessed for the photocatalytic labeling of proteins. “TagC-RED,” a Retro-Ene type sigmatropic rearrangement of Diazonium compounds for Cysteine-specific tagging, activated by near-infrared light (λ > 1000 nm), is also introduced and detailed in this report. TagC-RED is rapid, catalyst-free, compatible in cellular environments, and capable of penetrating tissues, making it suitable for intracellular labeling. This method holds significant potential as a platform for targeted protein labeling and real-time tracking of cellular processes. In parallel, foundational efforts to enable the specific spatiotemporal labeling of target sites on polynucleotides are also detailed here. Instead of the diazonium-mediated method used for light-controlled and site-selective labeling in proteins, DNA_x005f_x0002_photocatalyst chimera complexes were synthesized and designed to achieve site-selective modification of polynucleotides. Preliminary results demonstrated that each component of these photocatalyst-DNA chimera complexes retained its functional integrity: the photocatalyst maintained catalytic activity and the DNA retained hybridization capability. This emerging technology can address the long-standing challenge of site-specific DNA and RNA modification, enabling the photocatalytic incorporation of diverse natural and synthetic functional groups for the study of polynucleotide structure, dynamics, function, and therapeutic targeting.

Purchased from AmBeed: 25952-53-8 ; 15086-94-9 ; 1122-58-3

Modulating Hydrogel Stiffness Through Light-Based 3D Printing to Mimic Cardiac Fibrosis and Cardiomyocyte Dysfunction Using hiPSC-Derived Cells

Sohn, Sogu ; Momtahan, Nima ; Stevens, Lynn M ; Han, Jiwan ; Liu, Yutong ; Kiker, Meghan T , et al.

DOI: 10.1101/2025.05.20.655137 bioRxiv,2025.

Abstract: The human heart’s limited regenerative capacity is a significant barrier to addressing cardiovascular disease (CVD). This is particularly true for cardiac fibrosis, a form of CVD wherein the wound healing process has gone awry. In cardiac fibrosis, excessive scar tissue formation due to dysregulated remodeling of the heart’s extracellular matrix (ECM) results in increased stiffness that reduces cardiac output and can lead to heart failure. This dysregulated ECM deposition is driven by activated cardiac fibroblasts, where cell substrate stiffness is known to play a role in cardiac fibroblast activation. New preclinical models that accurately recapitulate the behavior of activated cardiac fibroblasts are needed to better understand and treat cardiac fibrosis. To this end, we describe a model wherein human induced pluripotent stem cell (hiPSC)-derived cardiac fibroblasts (HCFs) are cultured on 3D printed hydrogels of tunable stiffness, fabricated using dosage controlled digital light processing (DLP). We demonstrate that our model can induce HCF activation in the absence of TGFβ, a key mediator of fibroblast activation, surpassing the activation levels seen with HCFs activated with TGFβ on protein-coated tissue culture plates. Furthermore, combining stiffer hydrogels with TGFβ recapitulates fibroblast activation similar to what is observed in native cardiac tissue. Lastly, by indirectly coculturing HCFs seeded and activated on these stiff hydrogels with hiPSC-derived cardiomyocytes, we demonstrate that the activated HCFs in our cardiac fibrosis model can impair cardiomyocyte function, mimicking the deleterious effects of cardiac fibrosis.

Purchased from AmBeed: 25952-53-8 ; 85073-19-4

Synthesis and evaluation of folic acid-conjugated MSNs for pH-responsive delivery of epirubicin with enhanced cytotoxic properties

Masood, Farha ; Ullah, Ashan ; ul Haq, Inam ; ul Ain, Noor ; Perveen, Kousar ; Aslam, Aqsa

DOI: 10.1016/j.colsurfa.2025.138308 Colloids Surf. A: Physicochem. Eng. Asp.,2025,138308.

Abstract: Tumor-targeted and controlled release of epirubicin (EPI) are two promising strategies to improve chemotherapy efficacy while reducing systemic side effects. In this study, mesoporous silica nanoparticles (MSNs) were synthesized via the sol–gel method and functionalized through different surface modification approaches. In the first approach, nanoparticles were loaded with variable amounts (2, 4, and 8 mg) of epirubicin. In the second approach, epirubicin-loaded nanoparticles were coated with chitosan (CS) to improve stability and pH-responsive release. In the third approach, MSNs were modified with (3-aminopropyl)triethoxysilane to produce amine-functionalized nanoparticles. These amine-functionalized MSNs were then coated with chitosan and loaded with epirubicin. In a parallel strategy, folic acid (FA) was conjugated to the amine-functionalized nanoparticles to enable tumor targeting, followed by drug loading. The folic acid-modified nanoparticles showed an encapsulation efficiency of 19.17±1.60% and a drug loading content of 1.93±0.52%. In vitro drug release studies demonstrated a pH-dependent sustained release profile, with 67.2±0.29% cumulative release at pH 5.5 after 28 h compared to 47.88±0.20% from free EPI within 1 h. Release kinetics followed the Higuchi model. Cytotoxicity studies revealed a 3.16-fold enhancement in anticancer activity against MCF-7 breast cancer cells compared to free epirubicin. These results suggest that the folic acid-functionalized MSNs are a promising pH-responsive drug delivery system for targeted cancer therapy.

Keywords: Mesoporous silica nanoparticles ; epirubicin ; pH-responsive release ; surface modification ; targeted cancer therapy

Purchased from AmBeed: 25952-53-8

Structure-Based Drug Design of ADRA2A Antagonists Derived from Yohimbine

Artem Chayka ; Michal Česnek ; Erika Kužmová ; Jaroslav Kozák ; Eva Tloušt' ; ová , et al.

DOI: 10.1021/acs.jmedchem.4c00323 PubMed ID: 38857067 JMC,2024,67(12):10135-10151.

Abstract: Yohimbine, a natural indole alkaloid and a nonselective adrenoceptor antagonist, possesses potential benefits in treating inflammatory disorders and sepsis. Nevertheless, its broader clinical use faces challenges due to its low receptor selectivity. A structure–activity relationship study of novel yohimbine analogues identified amino esters of yohimbic acid as potent and selective ADRA2A antagonists. Specifically, amino ester 4n, in comparison to yohimbine, showed a 6-fold higher ADRA1A/ADRA2A selectivity index (SI > 556 for 4n) and a 25-fold higher ADRA2B/ADRA2A selectivity index. Compound 4n also demonstrated high plasma and microsomal stability, moderate-to-low membrane permeability determining its limited ability to cross the blood–brain barrier, and negligible toxicity on nontumor normal human dermal fibroblasts. Compound 4n represents an important complementary pharmacological tool to study the involvement of adrenoceptor subtypes in pathophysiologic conditions such as inflammation and sepsis and a novel candidate for further preclinical development to treat ADRA2A-mediated pathologies.

Purchased from AmBeed: 25952-53-8 ; 36805-97-7 ; 6674-22-2

Mimicking Charged Host-Defense Peptides to Tune the Antifungal Activity and Biocompatibility of Amphiphilic Polymers

Sebastian Schaefer ; Daniele Melodia ; Christopher Pracey ; Nathaniel Corrigan ; Megan D. Lenardon ; Cyrille Boye

DOI: 10.1021/acs.biomac.3c01038 Biomacromolecules,2024,25(2):871-889.

Abstract: Invasive fungal infections impose a substantial global health burden. They cause more than 1.5 million deaths annually and are insufficiently met by the currently approved antifungal drugs. Antifungal peptides are a promising alternative to existing antifungal drugs; however, they can be challenging to synthesize, and are often susceptible to proteases in vivo. Synthetic polymers which mimic the properties of natural antifungal peptides can circumvent these limitations. In this study, we developed a library of 29 amphiphilic polyacrylamides with different charged units, namely, amines, guanidinium, imidazole, and carboxylic acid groups, representative of the natural amino acids lysine, arginine, histidine, and glutamic acid. Ternary polymers incorporating primary ammonium (lysine-like) or imidazole (histidine-like) groups demonstrated superior activity against Candida albicans and biocompatibility with mammalian cells compared to the polymers containing the other charged groups. Furthermore, a combination of primary ammonium, imidazole, and guanidinium (arginine-like) within the same polymer outperformed the antifungal drug amphotericin B in terms of therapeutic index and exhibited fast C. albicans-killing activity. The most promising polymer compositions showed synergistic effects in combination with caspofungin and fluconazole against C. albicans and additionally demonstrated activity against other clinically relevant fungi. Collectively, these results indicate the strong potential of these easily producible polymers to be used as antifungals.

Purchased from AmBeed: 25952-53-8

The Influence of Various Crosslinking Conditions of EDC/NHS on the Properties of Fish Collagen Film

Alina Sionkowska ; Karolina Kulka-Kamińska ; Patrycja Brudzyńska ; Katarzyna Lewandowska ; Łukasz Piwowarski ;

DOI: 10.3390/md22050194 Mar. Drugs,2024,22(5):194.

Abstract: The process of crosslinking improves the physicochemical properties of biopolymer-based composites, making them valuable for biomedical applications. EDC/NHS-crosslinked collagen materials have a significant potential for tissue engineering applications, due to their enhanced properties and biocompatibility. Chemical crosslinking of samples can be carried out in several ways, which is crucial and has a direct effect on the final properties of the obtained material. In this study, the effect of crosslinking conditions on the properties of collagen films using EDC and NHS was investigated. Studies included FTIR spectroscopy, AFM, swelling and degradation tests, mechanical testing and contact angle measurements. Evaluation of prepared collagen films indicated that both crosslinking agents and crosslinking conditions influenced film properties. Notable alternations were observed in the infrared spectrum of the sample, to which EDC was added directly to the fish collagen solution. The same sample indicated the lowest Young modulus, tensile strength and breaking force parameters and the highest elongation at break. All samples reached the maximum swelling degree two hours after immersion in PBS solution; however, the immersion-crosslinked samples exhibited a significantly lower degree of swelling and were highly durable. The highest roughness was observed for the collagen film crosslinked with EDC, whereas the lowest was observed for the specimen crosslinked with EDC with NHS addition. The crosslinking agents increased the surface roughness of the collagen film, except for the sample modified with the addition of EDC and NHS mixture. All films were characterized by hydrophilic character. The films’ modification resulted in a decrease in their hydrophilicity and wettability. Our research allows for a comparison of proposed EDC/NHS crosslinking conditions and their influence on the physicochemical properties of fish collagen thin films. EDC and NHS are promising crosslinking agents for the modification of fish collagen used in biomedical applications.

Keywords: fish collagen ; EDC ; NHS ; crosslinking ; biopolymer film

Purchased from AmBeed: 25952-53-8

Surface-Modified Nanoparticles Based on Ibuprofen Prodrug and Exploring Its Anti-inflammatory and Anti-Cancer Potential

Shahida Muhammad Habib ; Muhammad Imran ; Farheen Mansoor ; Nimra Naz Siddiqui ; Almas Jabeen ; Humera Jahan , et al.

DOI: 10.1016/j.jddst.2024.106021 J. Drug. Deliv. Sci. Tec.,2024,106021.

Abstract: Cancer aggressiveness and metastases represent a major cause of death worldwide. Cyclooxygenase-2 (COX-2) and its metabolites significantly influence tumor development and metastatic processes. The design and synthesis of prodrugs intended for nonsteroidal anti-inflammatory drugs (NSAIDs) have garnered considerable attention from medicinal chemists, particularly in the last decade. A pH-sensitive drug delivery carrier based on TEG-derivatized ibuprofen Ibu-TEG was synthesized to serve as a dual-delivery system for anti-inflammatory and anticancer agents. The successful synthesis was confirmed through various spectroscopic techniques. This amphiphilic and biodegradable prodrug was self-assembled into micellar nanoparticles (Ibu-TEG-NPs). Their surface was subsequently modified with biocompatible molecules, chitosan (Ibu-TEG-NPs-CHI) and poly-dopamine (Ibu-TEG-NPs-PDA), to enhance drug efficacy and thermal stability. As-prepared NPs were characterized through FT-IR, DLS, TGA, AFM, and SEM. These surface-modified NPs were significantly active against ROS and NO generation and showed a lower IC₅₀ value than Ibuprofen. Moreover, Ibu-TEG-NPs, Ibu-TEG-NPs-CHI, and Ibu-TEG-NPs-PDA revealed significant therapeutic activity against Lung-NCI-H460 and Hepato-HepG2 cancer cell lines, demonstrating low IC₅₀ values.

Purchased from AmBeed: 25952-53-8

Activity of Alkoxyamide-Based Histone Deacetylase Inhibitors Against Plasmodium Falciparum Malaria Parasites

Wisam A. Dawood ; Gillian M. Fisher ; Franziska J.M. Kinnen ; Christian Anzenhofer ; Tina Skinner-Adams ; Leandro Alves Avelar , et al.

DOI: 10.1016/j.exppara.2024.108716 Exp. Parasitol.,2024,258,108716.

Abstract: There are more than 240 million cases of malaria and 600,000 associated deaths each year, most due to infection with Plasmodium falciparum parasites. While malaria treatment options exist, new drugs with novel modes of action are needed to address malaria parasite drug resistance. Protein lysine deacetylases (termed HDACs) are important epigenetic regulatory enzymes and prospective therapeutic targets for malaria. Here we report the antiplasmodial activity of a panel of 17 hydroxamate zinc binding group HDAC inhibitors with alkoxyamide linkers and different cap groups. The two most potent compounds (4a and 4b) were found to inhibit asexual P. falciparum growth with 50% inhibition concentrations (IC50's) of 0.07 μM and 0.09 μM, respectively, and demonstrated >200-fold more selectivity for P. falciparum parasites versus human neonatal foreskin fibroblasts (NFF). In situ hyperacetylation studies demonstrated that 4a, 4b and analogs caused P. falciparum histone H4 hyperacetylation, suggesting HDAC inhibition, with structure activity relationships providing information relevant to the design of new Plasmodium-specific aliphatic chain hydroxamate HDAC inhibitors.

Keywords: HDAC inhibitor ; Malaria ; P. falciparum ; Antiplasmodial

Purchased from AmBeed: 25952-53-8 ; 149647-78-9 ; 617-86-7

Drug modifications: graphene oxide-chitosan loading enhanced anti-amoebic effects of pentamidine and doxycycline

Jabri, Tooba ; Daalah, Meshal ; Alawfi, Bader S ; Gul, Jasra ; Ahmed, Usman ; Shah, Muhammad Raza , et al.

DOI: 10.1007/s00436-024-08389-6 PubMed ID: 39565414 Parasitol. Res.,2024,123,387.

Abstract: Acanthamoeba castellanii is the causative pathogen of a severe eye infection, known as Acanthamoeba keratitis and a life-threatening brain infection, named granulomatous amoebic encephalitis. Current treatments are problematic and costly and exhibit limited efcacy against Acanthamoeba parasite, especially the cyst stage. In parallel to drug discovery and drug repurposing eforts, drug modifcation is also an important approach to tackle infections, especially against neglected parasites such as free-living amoebae: Acanthamoeba. In this study, we determined whether modifying pentamidine and doxycycline through chitosan-functionalized graphene oxide loading enhances their anti-amoebic efects. Various concentrations of doxycycline, pentamidine, graphene oxide, chitosan-functionalized graphene oxide, and chitosan-functionalized graphene oxide loaded with doxycycline and pentamidine were investigated for amoebicidal efects against pathogenic A. castellanii belonging to the T4 genotype. Lactate dehydrogenase assays were performed to determine toxic efects of these various drugs and nanoconjugates against human cells. The fndings revealed that chitosan-functionalized graphene oxide loaded with doxycycline demonstrated potent amoebicidal efects. Nanomaterials signifcantly (p<0.05) inhibited excystation and encystation of A. castellanii without exhibiting toxic efects against human cells in a concentration-dependent manner, as compared with other formulations. These results indicate that drug modifcations coupled with nanotechnology may be a viable avenue in the rationale development of efective therapies against Acanthamoeba infections.

Keywords: Drug modifcation ; Graphene oxide ; Chitosan ; Doxycycline ; Pentamidine ; Acanthamoeba

Purchased from AmBeed: 25952-53-8

Alternative Method for Immobilization of Molecular Electrocatalyst on Carbon Electrode Surfaces via the Diels-Alder Reaction

Ali Abed, Hussain ;

Abstract: A new method for the surface functionalization of redox active compounds onto carbon electrodes via a cupper catalyzed Diels-Alder reaction has been previously investigated by Leroux et.al, were they showed that under mild conditions and short reaction times, the surface functionalization of ferrocene substituted with an alkyl chain resulted in high surface coverage on the electrode with good electrical properties. The research presented in this report aims to extend the scope of the Diels-Alder surface functionalization employing other redox active compounds primarily targeting future applications towards heterogenous electrocatalysis. Glassy carbon electrode which, due the large abundance of sp²-hybridized carbons, makes them ideal for Diels-Alder functionalization.The dienophile in the immobilization protocol is a terminal alkynyl ester. Out of the six compounds we initially intended to synthesis we successfully prepared four. For the three synthesised redox active species, electrochemical characterisations were performedfor two of them after surface immobilization, and for one in solution using cyclic voltammetry. The study proved that the surface immobilization was successful with a surface coverage of 2.84 x 10 ^-11 mol/cm² for anodic current and 4.49 x 10 ^-11 mol/cm² for cathodic current for 1. Compared to the surface coverage reported by Leroux et.al. of (3.31 ± 0.22) x 10 ^-10 mol/cm², which is a 10-fold higher than what this study found.The surface coverage for 5 was measuredto 2.36 x 10 ^-11 mol/cm² for anodic current and 3.18 x 10 ^-11 mol/cm² for the cathodic current. The obtained surface coverage of these compounds were lower than those reported in the published results by Leroux et.al. Further investigation into the surface immobilization procedure is necessary to identify the factors causing the low surface coverage.

Purchased from AmBeed: 25952-53-8 ; 1122-58-3 ; 29280-41-9

EVALUATION OF AMINOINDOLE CARBOXAMIDES AND TRIAZINES AS POTENTIAL ANTI-AGGREGATION AGENTS OF PROTEIN MISFOLDING DISEASES

Eduardo Ramirez ;

DOI: 10.25394/PGS.25685910.v1 Purdue University Graduate School,2024.

Abstract: Alzheimer’s (AD) and Parkinson’s (PD) are the most common debilitating disorders to affect the geriatric population. There are two pathological hallmarks which correlate with the manifestation of AD: the first is the formation amyloid-β plaques (Aβ plaques) in the extracellular space and the second is the aggregation of hyperphosphorylated tau protein (p-tau) which develops into neurofibrillary tangles (NFTs) in the interneuron. PD results from the misfolding of α-synuclein (α-syn) which then aggregates to form Lewy bodies. In over 50% of AD cases aggregated α-syn_x005f_x0002_containing Lewy bodies are presently displayed. My research projects focus on the dual targeting of small molecules to abrogate aberrant α-syn, tau (2N4R), and p-tau (1N4R) aggregation and to reduce the spread of AD and related dementias. Not very many drug discovery programs focus on the specific isoforms of the tau protein. We set out to establish two series of aminoindole compounds connected by a carboxamide or triazine linker to evaluate the effectiveness of both families in decreasing the amount of misfolded α-syn and tau protein. Biophysical methods such as thioflavin T (ThT) fluorescence assays, photoinduced cross-linking of unmodified proteins (PICUP), and transmission electron microscopy (TEM) were deployed to assess the anti_x005f_x0002_aggregation potential of our aminoindole derivatives. M17D intracellular inclusion assay was used to detect the potency of our best compounds in reducing α-syn inclusions. We found that compounds A2, A8, and A17 from the amide series and compound T10 from the triazine series were effective in reducing the formation of α-syn and tau isoform 2N4R fibrils and oligomers in a dose-dependent manner. This was observed through the use of ThT fluorescence and PICUP assays and was validated with TEM. These same compounds reduced the development of α-syn inclusions in M17D neuroblastoma cells. Compounds A8 of the amide project and T10 of the triazine series were the most effective in preventing α-syn and tau isoform 2N4R aggregation. Compound T10 also showed reduction of ex vivo Aβ plaques and paired helical filaments (PHFs) in the brain tissue of a deceased AD patient showcasing its translational potential. These results demonstrate the potential of 4-aminoindole derivatives in preventing the aggregation α-syn and tau (2N4R isoform) proteins. The triazine derivatives series demonstrates the effectiveness of N_x005f_x0002_linked triazines in reducing misfolding of α-syn and tau in contrast to O-linked triazines and display the importance of symmetry in drug design.

Keywords: Alzheimer's disease ; Amide ; alpha-synuclein (synuclein alpha) ; fibril oligomer ; tau isoform 2n4r ; anti-aggregation compounds ; hyperphosphorylated protein tau ; paired helical filaments ; drug discovery ; triazine compound

Purchased from AmBeed: 25952-53-8 ; 153-78-6 ; 74-11-3 ; 1122-58-3

Polar order in a fluid like ferroelectric with a tilted lamellar structure--observation of a polar smectic C (SmCp) phase

Hobbs, Jordan ; Gibb, Calum J ; Pociecha, Damian ; Szydłowska, Jadwiga ; Górecka, Ewa ; Mandle, Richard J

DOI: 10.48550/arXiv.2408.15859 arXiv,2024,2408.15859.

Abstract: The discovery of fluid states of matter with spontaneous bulk polar order is appreciated as a major discovery in the fields of soft matter and liquid crystals. Typically, this manifests as polar order superimposed atop conventional phase structures and is thus far limited to orthogonal phase types. Here we report a family of materials which exhibit a previously unseen state of matter which we conclude is a polar smectic C phase, and so we term it SmC_P. The spontaneous polarisation of the SmC_P phase is over two orders of magnitude larger than that found in conventional ferroelectric SmC phase of chiral materials used in some LCD devices. Fully atomistic molecular dynamics simulations faithfully and spontaneously reproduce the proposed structure and associated bulk properties; comparison of experimental and simulated X-ray scattering patterns shows excellent agreement. The materials disclosed here have significantly smaller dipole moments than typical polar liquid crystals such as RM734 which suggests the role of molecular electrical polarity in generating polar order is perhaps overstated, a view supported by consideration of other molecular systems.

Purchased from AmBeed: 1122-58-3 ; 5731-13-5 ; 25952-53-8 ; 335125-98-9

SAR study of piperidine derivatives as inhibitors of 1,4-dihydroxy-2-naph- thoate isoprenyltransferase (MenA) from Mycobacterium tuberculosis

Berg, Kaja ; Hegde, Pooja ; Pujari, Venugopal ; Brinkmann, Marzena ; Wilkins, David Z. ; Parish, Tanya , et al.

DOI: 10.1016/j.ejmech.2023.115125 PubMed ID: 36682292 Eur. JMC,2023,249,115125.

Abstract: The electron transport chain (ETC) in the cell membrane consists of a series of redox complexes that transfer electrons from electron donors to acceptors and couples this electron transfer with the transfer of protons (H+) across a membrane. This process generates proton motive force which is used to produce ATP and a myriad of other functions and is essential for the long-term survival of Mycobacterium tuberculosis (Mtb), the causative organism of tuberculosis (TB), under the hypoxic conditions present within infected granulomas. Menaquinone (MK), an important carrier molecule within the mycobacterial ETC, is synthesized de novo by a cluster of enzymes known as the classic/canonical MK biosynthetic pathway. MenA (1,4-dihydroxy-2-naphthoate prenyltransferase), the antepenultimate enzyme in this pathway, is a verified target for TB therapy. In this study, we explored structure-activity relationships of a previously discovered MenA inhibitor scaffold, seeking to improve potency and drug disposition properties. Focusing our campaign upon three molecular regions, we identified two novel inhibitors with potent activity against MenA and Mtb (IC50 = 13-22 μM, GIC50 = 8-10 μM). These analogs also displayed substantially improved pharmacokinetic parameters and potent synergy with other ETC-targeting agents, achieving nearly complete sterilization of Mtb in combination therapy within two weeks in vivo. These new inhibitors of MK biosynthesis present a promising new strategy to curb the continued spread of TB.

Keywords: 1,4-dihydroxy-2-naphthoate prenyltransferase ; MenA ; MenA inhibitors ; Menaquinone ; Mtb ; Mycobacterium tuberculosis ; Piperidine derivatives ; SAR

Purchased from AmBeed: 25952-53-8 ; 90719-32-7 ; 872-85-5 ; 6457-49-4 ; 3769-41-3 ; 10338-57-5 ; 135-19-3 ; 135-19-3 ; 28177-48-2 ; 22246-18-0 ; 122334-37-6 ; 91914-06-6 ; 10040-98-9 ; 161975-39-9 ; 150-76-5 ; 371-41-5 ; 63754-96-1 ; 288-32-4 ; 3380-34-5 ; 1677-46-9 ; 166815-96-9 ; 700-57-2 ; 1204-86-0 ; 21725-69-9 ; 367-12-4 ; 1003-29-8 ; 627-35-0 ; 27292-49-5 ; 104324-16-5 ; 123855-51-6 ; 180847-23-8 ; 4328-13-6 ; 875401-70-0 ; 405272-71-1 ; 63614-86-8 ; 1420942-13-7 ; 25952-53-8 ; 1420895-21-1 ; 1078-18-8 ; 32363-45-4 ; 69564-68-7 ; 31519-22-9 ; 22246-18-0 ; 189618-33-5 ; 180847-24-9 ; 6264-98-8 ; 946680-75-7 ; 63608-38-8 ; 713-68-8 ; 62810-39-3 ; 189618-32-4 ; 63608-31-1 ; 15789-05-6 ; 63712-27-6 ; 63608-33-3 ; 63608-35-5

Shape matters: Effect of amphiphilic polymer topology on antibacterial activity and hemocompatibility

Md Aquib ; Sebastian Schaefer ; Hatu Gmedhin ; Nathaniel Corrigan ; Valentin A. Bobrin ; Cyrille Boyer

DOI: 10.1016/j.eurpolymj.2023.112698 Eur. Polym. J.,2023,205,112698.

Abstract: Understanding the intricate relationship between polymer architecture and biological activity is critical for advancing the development of antibacterial polymers. In this study, we systematically investigated the antibacterial properties and hemocompatibility of 27 different synthetic polymers prepared by reversible addition-fragmentation chain transfer (RAFT) polymerization. The antibacterial activities of these polymers were probed against two gram-negative bacteria, namely Pseudomonas aeruginosa PAO1 and Escherichia coli K12. Furthermore, the antibacterial efficacy and hemocompatibility of synthetic polymers were correlated with their polymer topology, encompassing linear (LPs), hyperbranched (HPs), and star polymers (SPs), characterized by varying hydrophobic compositions (20 %, 25 %, and 30 %). HPs were prepared using two types of crosslinking monomer (acrylate vs. acrylamide). The [crosslinker]:[RAFT agent] ratio in the synthesis of HPs greatly affect their hemocompatibility, while the type of crosslinker had a negligible impact. HPs showed a remarkable 2- to 4-fold enhancement in hemocompatibility compared to LPs at the same hydrophobic ratio. Interestingly, SPs with a low hydrophobic ratio, did not display toxicity towards red blood cells, while maintaining similar potent antibacterial activities as LPs and HPs. Overall, SPs exhibited superior bioactivity compared to HPs and LPs (SPs > HPs > LPs), demonstrating that the manipulation of polymer topology offers a promising avenue for enhancing the performance of synthetic antibacterial polymers.

Keywords: Amphiphilic polymer ; Structure-bioactivity relationship ; Antibacterial activity ; Hemocompatibility ; Antibacterial polymer

Purchased from AmBeed: 25952-53-8

Antibacterial Properties of Ethacridine Lactate and Sulfmethoxazole Loaded Functionalized Graphene Oxide Nanocomposites

Tooba Jabri ; Naveed Ahmed Khan ; Zinb Makhlouf ; Noor Akbar ; Jasra Gul ; Muhammad Raza Shah , et al.

DOI: 10.3390/antibiotics12040755 PubMed ID: 37107117 Antibiotics,2023,12(4):755.

Abstract: The emergence of drug-resistant bacterial strains that reduce the effectiveness of antimicrobial agents has become a major ongoing health concern in recent years. It is therefore necessary to find new antibacterials with broad-spectrum activity against both Gram-positive and Gram-negative bacteria, and/or to use nanotechnology to boost the potency of already available medications. In this research, we examined the antibacterial efficacy of sulfamethoxazole and ethacridine lactate loaded two-dimensional glucosamine functionalized graphene-based nanocarriers against a range of bacterial isolates. Graphene oxide was first functionalized with glucosamine, which as a carbohydrate moiety can render hydrophilic and biocompatible characters to the GO surface, and subsequently loaded with ethacridine lactate and sulfamethoxazole. The resulting nanoformulations had distinct, controllable physiochemical properties. By analyzing the formulation using Fourier Transform Infrared Spectroscopy (FTIR), X-ray diffraction (PXRD), a thermogravimetric analysis (TGA), zetasizer, and a morphological analysis using Scanning Electron Microscopy and Atomic Force Microscopy, researchers were able to confirm the synthesis of nanocarriers. Both nanoformulations were tested against Gram-negative bacteria, including Escherichia coli K1, Serratia marcescens, Pseudomonas aeruginosa, Salmonella enterica, as well as Gram-positive bacteria, including Bacillus cereus, Streptococcus pyogenes, and Streptococcus pneumoniae. Importantly, ethacridine lactate and its nanoformulations exhibited significant antibacterial properties against all bacteria tested in this study. When tested for minimum inhibitory concentration (MIC), the results were remarkable and revealed that ethacridine lactate presented MIC90 at 9.7 µg/mL against S. enteric, and MIC90 at 6.2 µg/mL against B. cereus. Notably, ethacridine lactate and its nanoformulations showed limited toxicity effects against human cells using lactate dehydrogenase assays. Overall, the results revealed that ethacridine lactate and its nanoformulations possess antibacterial activities against various Gram-negative and Gram-positive bacteria and that nanotechnology can be employed for the targeted delivery of effective drugs without harming the host tissue

Keywords: antimicrobial resistance ; graphene oxide ; ethacridine lactate ; sulfamethoxazole ; glucosamine

Purchased from AmBeed: 25952-53-8

Product Details of EDC·HCl

CAS No. :	25952-53-8
Formula :	C₈H₁₈ClN₃
M.W :	191.70
SMILES Code :	CCN=C=NCCCN(C)C.[H]Cl
MDL No. :	MFCD00012503
InChI Key :	FPQQSJJWHUJYPU-UHFFFAOYSA-N
Pubchem ID :	2723939

Safety of EDC·HCl

GHS Pictogram:
Signal Word:	Danger
Hazard Statements:	H302-H311-H315-H317-H373-H410
Precautionary Statements:	P260-P264-P270-P272-P273-P280-P301+P312+P330-P302+P352+P312-P314-P333+P313-P391-P405-P501
Class:	6.1
UN#:	2811
Packing Group:	Ⅲ

Application In Synthesis of EDC·HCl

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 25952-53-8 ]

[ 25952-53-8 ] Synthesis Path-Downstream 1~9

1
[ 29006-02-8 ]
[ 870-46-2 ]
[ 25952-53-8 ]
[ 374889-93-7 ]

Yield	Reaction Conditions	Operation in experiment
57%	In pyridine; ethyl acetate;	(1) Carbazic acid tert-butyl ester (9.21 g) was dissolved in pyridine (120 ml), followed by addition of <strong>[29006-02-8]4-methoxybutyric acid</strong> (9.06 g) and 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride salt (20.0 g), and stirred at ambient temperature for 64 hours. After the reaction solution was concentrated under reduced pressure, ethyl acetate was added to the residue, which was then washed with aqueous 1 mol/liter hydrochloric acid solution, saturated aqueous sodium hydrogen carbonate solution and saturated aqueous sodium chloride, and dried over anhydrous sodium sulfate. After the solvent was evaporated under reduced pressure, N'-(4-methoxybutyryl) hydrazine carboxylic acid tert-butyl ester was obtained in yellow oil (9.30 g, 57%). The physico-chemical values are as follows. 1H-NMR (DMSO-d6) delta: 1.39 (9H, s), 1.65-1.78 (2H, m), 2.07-2.12 (2H, m), 3.21 (3H, s), 3.30-3.34 (2H, m), 8.64 (1H, s), 9.46 (1H, s).

References: [1]Patent: US2003/216385,2003,A1 .

2
[ 1570-05-4 ]
[ 25952-53-8 ]
[ 198554-72-2 ]
[ 198554-80-2 ]

Yield	Reaction Conditions	Operation in experiment
	With benzotriazol-1-ol; In dichioromethane;	(1) 2-Amino-4-[1-(3,4-dibenzyloxybenzoyl)-4-piperidinyl]-6-(4-methoxyphenylmethyl) pyrimidine STR73 To a solution of 2-amino-4-(4-methoxyphenylmethyl)-6-(4-piperidinyl)pyrimidine (160 mg, 0.54 mmol), <strong>[1570-05-4]3,4-dibenzyloxybenzoic acid</strong> (179 mg, 0.54 mmol) and 1-hydroxybenzotriazole (72 mg, 0.54 mmol) in dichioromethane (150 ml) were added 1-ethyl-3-(N, N'-dimethylaminopropyl)carbodiimide hydrochloride (103 mg, 0.54 mmol) at room temperature under nitrogen atmosphere. After stirring for about 30 minutes, the mixture was washed successively with saturated sodium hydrogen carbonate solution and brine. The organic layer was dried over anhydrous sodium sulfate and then evaporated. The residue was purified by column chromatography (chloroform:methanol=99:1) to give the titled compound (477 mg). 1 H-NMR (CDCl3): delta 1.77 (4H, m), 2.59 (1H, m), 2.84 (2H, m), 3.78 (3H, s), 3.82 (2H, s), 3.90 (1H, m), 4.70 (1H, m), 5.11 (2H, s), 5.17 (2H, s), 5.18 (2H,s), 6.24 (1H, s), 6.84-7.00 (5H, m), 7.14-7.44 (12H, m).

References: [1]Patent: US5948786,1999,A .

3
[ 6066-82-6 ]
[ 150349-65-8 ]
[ 25952-53-8 ]
[ 198895-68-0 ]
N-[3-(1-tert-butoxycarbonyl-4-piperidyl)propan-1-yl]-5-thia-1,8b-diazaacenaphthylene-4-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium chloride; In chloroform; acetonitrile;	1) Synthesis of N-[3-(1-tert-butoxycarbonyl-4-piperidyl)propan-1-yl]-5-thia-1,8b-diazaacenaphthylene-4-carboxamide In acetonitrile (120 ml) was suspended 6.55 g (30.0 mM) of 5-thia-1,8b-diazaacenaphthylene-4-carboxylic acid as well as 6.91 g (60.0 mM) of N-hydroxysuccinimide, followed by additino of 11.50 g (60.0 mM) of N-ethyl-N'-3-(N,N-dimethylamino)propylcarbodiimide hydrochloride, and the mixture was stirred at room temperature for 1 hour. The solvent was then distilled off under reduced pressure and the residue was extracted with chloroform. The organic layer was washed with saturated aqueous solution of sodium chloride and dried over MgSO4 and the solvent was distilled off under reduced pressure to provide the active ester. To a solution of this active ester in chloroform (100 ml) was added 8.4 ml (60.0 mM) m of triethylamine as well as 8.72 g (36.0 mM) of 3-(1-tert-butoxycarbonyl-4-piperidyl)propylamine and the mixture was stirred at room temperature for 30 minutes. This reaction mixture was washed with purified water and the organic layer was further washed with saturated m aqueous solution of sodium chloride. After the organic layer was dried over MgSO4, the solvent was distilled off under reduced pressure and the residue was purified by column chromatography (ethyl acetate/ethanol=10/1) to provide the title compound. Red solid. Yield 10.16 g (76%) 1H-NMR (200 MHz, CDCl3) delta: 0.95-1.41 (m, 4H), 1.45 (s, 9H), 1.48-1.72 (m, 5H), 2.61-2.73 (m, 2H), 3.28 (m, 2H), 4.05-4.14 (m, 2H), 5.79 (dd, J=2.2, 5.8 Hz, 1H), 6.02 (t, J=5.6 Hz, 1H), 6.63-6.70 (m, 3H), 7.02 (s, 1H). IR (KBr): 1684, 1624, 1278, 1161 cm-1.

References: [1]Patent: US6235731,2001,B1 .

4
[ 6638-79-5 ]
[ 2592-95-2 ]
[ 25952-53-8 ]
[ 207994-08-9 ]
[ 1600511-96-3 ]

Yield	Reaction Conditions	Operation in experiment
	With triethanolamine; In n-heptane; dichloromethane;	Step 1: 5-Chloro-3-fluoro-N-methoxy-N-methylpicolinamide To a stirred mixture of <strong>[207994-08-9]5-chloro-3-fluoropicolinic acid</strong> (3.62 g, 20.62 mmol) in dichloromethane (50 mL) were added 1H-benzo[d][1,2,3]triazol-1-ol (0.42 g, 3.09 mmol), N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine HCl (5.93 g, 30.9 mmol), N,O-dimethylhydroxylamine HCl (3.02 g, 30.9 mmol), and TEA (7.19 mL, 51.6 mmol). The reaction mixture was stirred at RT for 2 hours, and then partitioned between ethyl acetate and water. The aqueous layer was extracted with EtOAc, and the combined organic layers were dried over anhydrous sodium sulfate, filtered, and concentrated. The crude product was purified by column chromatography, eluting with 0-100% EtOAc in heptane, to provide the title intermediate (3.71 g) as a white solid.

References: [1]Patent: US2014/107109,2014,A1 .Location in patent: Page/Page column.

5
[ 37718-11-9 ]
tert-butyl [trans-2-(4-aminophenyl)cyclopropyl](cyclopropylmethyl)carbamate [ No CAS ]
[ 25952-53-8 ]
tert-butyl (cyclopropylmethyl)(trans-2-{4-[(1H-pyrazol-4-ylcarbonyl)amino]phenyl}cyclopropyl)carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide;	A) tert-butyl (cyclopropylmethyl)(trans-2-{4-[(1H-pyrazol-4-ylcarbonyl)amino]phenyl}cyclopropyl)carbamate A solution of tert-butyl [trans-2-(4-aminophenyl)cyclopropyl](cyclopropylmethyl)carbamate (75 mg) in DMF (3 mL) was ice-cooled, and <strong>[37718-11-9]1H-<strong>[37718-11-9]pyrazole-4-carboxylic acid</strong></strong> (33.4 mg), N-ethyl-N'-(3-dimethylaminopropyl)carbodiimide hydrochloride (143 mg), 1-hydroxybenzotriazole (49.4 mg) and diisopropylethylamine (80 mg) were added. The mixture was stirred at room temperature overnight, and saturated aqueous sodium hydrogen carbonate solution was added under ice-cooling. The mixture was extracted with ethyl acetate, and the extract was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (72 mg). MS (API+): [M-tBu+2H]+ 341.0.

References: [1]Patent: EP2743256,2014,A1 .Location in patent: Page/Page column.

6
tert-butyl [trans-2-(4-aminophenyl)cyclopropyl](cyclopropylmethyl)carbamate [ No CAS ]
[ 582-80-9 ]
[ 25952-53-8 ]
tert-butyl [trans-2-(4-[4-(benzoylamino)benzoyl]amino}-phenyl)cyclopropyl](cyclopropylmethyl)carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With benzotriazol-1-ol; In N,N-dimethyl-formamide;	A) tert-butyl [trans-2-(4-[4-(benzoylamino)benzoyl]amino}-phenyl)cyclopropyl](cyclopropylmethyl)carbamate To a solution of tert-butyl [trans-2-(4-aminophenyl)cyclopropyl](cyclopropylmethyl)carbamate (90.9 mg), <strong>[582-80-9]4-benzamidobenzoic acid</strong> (87 mg) and 1-hydroxybenzotriazole (60.9 mg) in DMF (1.5 mL) was added N-ethyl-N'-(3-dimethylaminopropyl)carbodiimide hydrochloride (86 mg). The reaction mixture was stirred at room temperature for 2 hr, and poured into 0.5N hydrochloric acid. The mixture was extracted with ethyl acetate, and the extract was washed successively with water, saturated aqueous sodium hydrogen carbonate solution and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was washed with ethyl acetate/diisopropyl ether to give the title compound (98.0 mg). 1H NMR (300 MHz, DMSO-d6) delta 0.07-0.17 (1H, m), 0.18-0.29 (1H, m), 0.34-0.52 (2H, m), 0.91-1.02 (1H, m), 1.15-1.28 (2H, m), 1.37 (9H, s), 2.01-2.12 (1H, m), 2.67-2.76 (1H, m), 3.00 (1H, dd, J = 14.5, 7.0 Hz), 3.20 (1H, dd, J = 14.5, 6.9 Hz), 7.12 (2H, d, J = 8.7 Hz), 7.50-7.63 (3H, m), 7.67 (2H, d, J = 8.7 Hz), 7.91-8.01 (6H, m), 10.09 (1H, s), 10.51 (1H, s).

References: [1]Patent: EP2743256,2014,A1 .Location in patent: Page/Page column.

7
[ 4518-10-9 ]
[ 39968-33-7 ]
[ 25952-53-8 ]
[ 1204-06-4 ]
(E)-3-(3-1H-indol-3-yl-acryloylamino)-benzoic acid methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide;	1-3. Synthesis of Low-Molecular-Weight Compound ID-52 (8a) Among the above-described low-molecular-weight compounds, ID-52 (3-(3-1H-indol-3-yl-acryloylamino)-benzoic acid methyl ester (8a)) was prepared in the following manner. Trans-3-indoleacrylic acid (7a, 150 mg, 0.8 mmol) and 3-amino-benzoic acid methyl ester (6a, 218 mg, 1.44 mmol) were dissolved in DMF, and 1-[3-(dimethyamino)propyl]-3-ethylcarbodiimide hydrochloride (EDC, 230 mg, 1.2 mmol), hydroxy-7-azabenotriazole (HOAT, 163 mg, 1.2 mmol) and N,N-diisopropylethylamine (DIPEA, 0.21 mL, 1.2 mmol) were added to the solution to cause a coupling reaction. The reaction solution was stirred overnight at room temperature. Then, the resulting material was separated and purified to obtain 3-(3-1H-indol-3-yl-acryloylamino)-benzoic acid methyl ester (ID-52) as a yellow solid. 1H NMR (CDCl3, 300 MHz) d=8.90 (s, 1H), 8.21 (s, 1H), 7.86-8.03 (m, 4H), 7.76 (d, J=8.1 Hz, 1H), 7.36-7.41 (m, 3H), 7.20 (m, 2H), 6.60 (d, J=15.3 Hz, 2H), 3.88 (s, 3H).

References: [1]Patent: US2015/159142,2015,A1 .Location in patent: Page/Page column.

8
[ 35661-51-9 ]
[ 25952-53-8 ]
[ 76-05-1 ]

Yield	Reaction Conditions	Operation in experiment
	With benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine;	Trifluoroacetic Acid/tert-butyl {(2S)-4-[{(1R)-1-[1-benzyl-4-(2,5-difluorophenyl)-1H-imidazol-2-yl]-2,2-dimethylpropyl}(glycoloyl)amino]-1-hydrazino-1-oxobutan-2-yl}carbamate (1:1) 150 mg (0.16 mmol) of Intermediate C3 were dissolved in 21 ml of DMF, and then 37.2 mg (0.19 mmol) of N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride (EDC), 37 mg (0.243 mmol) of 1-hydroxybenzotriazole, 85 mul of N,N-diisopropylethylamine and finally 45 mg (0.18 mmol) of commercially available 9H-fluoren-9-ylmethyl hydrazinecarboxylate were added. The mixture was stirred at RT overnight and then concentrated under reduced pressure. The residue was purified by preparative HPLC. The appropriate fractions were concentrated and the residue was lyophilized from acetonitrile/water. This gave 60 mg (41percent of theory) of the protected intermediate.

References: [1]Patent: US2018/169256,2018,A1 .

9
[ 68176-57-8 ]
[ 25952-53-8 ]
5-(tert-butyl)-N-ethyl-1H-benzo[d]imidazol-2-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
94%	In isopropyl alcohol; at 80℃; for 0.25h;Microwave irradiation;	General procedure: A mixture of o-phenylenediamine (1.0 mmol) and EDC.HCl (1.1 mmol) in 2-propanol (10 mL) was irradiated in microwave apparatus at 200 W (80 °C) for 15 min. The reaction was monitored by TLC (eluent CH2Cl2 / MeOH 95:5). After completion, the reaction mixture was diluted with water (20 mL) and extracted with EtOAc (2 x 25 mL). The combined organic layers were washed with brine, dried over anhydrous Na2SO4 and concentrated under reduced pressure and the obtained crude product was purified by flash column chromatography using silica gel (100-200 mesh) with 1-5percent MeOH/CH2Cl2 as eluent. The fractions containing product were collected and concentrated under reduced pressure to afford N-ethyl-1Hbenzo[d]imidazol-2-amine (1a, 90percent yield) as an off white solid.

References: [1]Synthetic Communications,2019,vol. 49,p. 1308 - 1315.

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P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

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CAS No.: 25952-53-8

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CAS No.: 25952-53-8

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Product Details of EDC·HCl

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Application In Synthesis of EDC·HCl

[ 25952-53-8 ] Synthesis Path-Downstream 1~9

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