Home Cart 0 Sign in  

[ CAS No. 25952-53-8 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
HazMat Fee +

There will be a HazMat fee per item when shipping a dangerous goods. The HazMat fee will be charged to your UPS/DHL/FedEx collect account or added to the invoice unless the package is shipped via Ground service. Ship by air in Excepted Quantity (each bottle), which is up to 1g/1mL for class 6.1 packing group I or II, and up to 25g/25ml for all other HazMat items.

Type HazMat fee for 500 gram (Estimated)
Excepted Quantity USD 0.00
Limited Quantity USD 15-60
Inaccessible (Haz class 6.1), Domestic USD 80+
Inaccessible (Haz class 6.1), International USD 150+
Accessible (Haz class 3, 4, 5 or 8), Domestic USD 100+
Accessible (Haz class 3, 4, 5 or 8), International USD 200+
Chemical Structure| 25952-53-8
Chemical Structure| 25952-53-8
Structure of 25952-53-8 * Storage: {[proInfo.prStorage]}

Please Login or Create an Account to: See VIP prices and availability

Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Search after Editing

* Storage: {[proInfo.prStorage]}

* Shipping: {[proInfo.prShipping]}

Quality Control of [ 25952-53-8 ]

Related Doc. of [ 25952-53-8 ]

Alternatived Products of [ 25952-53-8 ]
Product Citations

Product Citations      Expand+

Artem Chayka ; Michal Česnek ; Erika Kužmová , et al. DOI: PubMed ID:

Abstract: Yohimbine, a natural 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 of yohimbic acid as potent and selective ADRA2A antagonists. Specifically, amino 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: ; ;

Sebastian Schaefer ; Daniele Melodia ; Christopher Pracey , et al. DOI:

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 drugs. are a promising alternative to existing drugs; however, they can be challenging to synthesize, and are often susceptible to proteases in vivo. Synthetic which mimic the properties of natural can circumvent these limitations. In this study, we developed a library of 29 amphiphilic polyacrylamides with different charged units, namely, , guanidinium, , and groups, representative of the natural lysine, arginine, , and . Ternary polymers incorporating primary ammonium (lysine-like) or (histidine-like) groups demonstrated superior activity against Candida albicans and biocompatibility with mammalian cells compared to the containing the other charged groups. Furthermore, a combination of primary ammonium, , and guanidinium (arginine-like) within the same polymer outperformed the drug 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 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 .

Purchased from AmBeed:

Alina Sionkowska ; Karolina Kulka-Kamińska ; Patrycja Brudzyńska , et al. DOI:

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:

Shahida Muhammad Habib ; Muhammad Imran ; Farheen Mansoor , et al. DOI:

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 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 and NO generation and showed a lower IC50 value than . 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:

Wisam A. Dawood ; Gillian M. Fisher ; Franziska J.M. Kinnen , et al. DOI:

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: ; ;

Jabri, Tooba ; Daalah, Meshal ; Alawfi, Bader S , et al. DOI: PubMed ID:

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:

Eduardo Ramirez ; DOI:

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: ; ; ;

Hobbs, Jordan ; Gibb, Calum J ; Pociecha, Damian , et al. DOI:

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 SmCP. The spontaneous polarisation of the SmCP 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: ; ; 25952-53-8 ;

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 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: ; ;

Berg, Kaja ; Hegde, Pooja ; Pujari, Venugopal , et al. DOI: PubMed ID:

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 ; ; ; ; ; ; 22246-18-0 ; ; ; ; ; ; ; ; ; ; ; ; ; ;

Md Aquib ; Sebastian Schaefer ; Hatu Gmedhin , et al. DOI:

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:

Tooba Jabri ; Naveed Ahmed Khan ; Zinb Makhlouf , et al. DOI: PubMed ID:

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:

Product Details of [ 25952-53-8 ]

CAS No. :25952-53-8 MDL No. :MFCD00012503
Formula : C8H18ClN3 Boiling Point : -
Linear Structure Formula :- InChI Key :FPQQSJJWHUJYPU-UHFFFAOYSA-N
M.W : 191.70 Pubchem ID :2723939
Synonyms :

Calculated chemistry of [ 25952-53-8 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.88
Num. rotatable bonds : 5
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 55.49
TPSA : 27.96 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.57 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 2.67
Log Po/w (WLOGP) : 1.93
Log Po/w (MLOGP) : 1.29
Log Po/w (SILICOS-IT) : 1.72
Consensus Log Po/w : 1.52

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.38
Solubility : 0.798 mg/ml ; 0.00416 mol/l
Class : Soluble
Log S (Ali) : -2.91
Solubility : 0.236 mg/ml ; 0.00123 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.12
Solubility : 1.45 mg/ml ; 0.00759 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.22

Safety of [ 25952-53-8 ]

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

Application In Synthesis of [ 25952-53-8 ]

* 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 ]
YieldReaction ConditionsOperation 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).
  • 2
  • [ 1570-05-4 ]
  • [ 25952-53-8 ]
  • [ 198554-72-2 ]
  • [ 198554-80-2 ]
YieldReaction ConditionsOperation 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).
  • 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 ]
YieldReaction ConditionsOperation 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.
  • 4
  • [ 6638-79-5 ]
  • [ 2592-95-2 ]
  • [ 25952-53-8 ]
  • [ 207994-08-9 ]
  • [ 1600511-96-3 ]
YieldReaction ConditionsOperation 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.
  • 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 ]
YieldReaction ConditionsOperation 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.
  • 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 ]
YieldReaction ConditionsOperation 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).
  • 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 ]
YieldReaction ConditionsOperation 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).
  • 8
  • [ 35661-51-9 ]
  • [ 25952-53-8 ]
  • [ 76-05-1 ]
YieldReaction ConditionsOperation 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.
  • 9
  • [ 68176-57-8 ]
  • [ 25952-53-8 ]
  • 5-(tert-butyl)-N-ethyl-1H-benzo[d]imidazol-2-amine [ No CAS ]
YieldReaction ConditionsOperation 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.
Recommend Products
Same Skeleton Products
Historical Records

Similar Product of
[ 25952-53-8 ]

Chemical Structure| 7084-11-9

A848717[ 7084-11-9 ]

N1-((Ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine xhydrochloride

Reason:

; ;