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Quality Control of [ 527-72-0 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 527-72-0 ]

Product Citations Expand+

Discovery of 4-aminoindole carboxamide derivatives to curtail alpha-synuclein and tau isoform 2N4R oligomer formation

Ramirez, Eduardo ; Min, Sehong ; Ganegamage, Susantha K. , et al. Results Chem.,2023,5,100938. DOI: 10.1016/j.rechem.2023.100938 PubMed ID: 37346091

Abstract: Alzheimer's disease (AD) is a multifactorial, chronic neurodegenerative disease characterized by the presence of extracellular beta-amyloid (Abeta) plaques, intraneuronal neurofibrillary tangles (NFTs), activated microglial cells, and an inflammatory state (involving reactive oxygen species production) in the brain. NFTs are comprised of misfolded and hyperphosphorylated forms of the microtubule-binding protein tau. Interestingly, the trimeric form of the 2N4R splice isoform of tau has been found to be more toxic than the trimeric 1N4R isoform in neuron precursor cells. Few drug discovery programs have focused on specific tau isoforms. The present drug discovery project is centered on the anti-aggregation effect of a series of seventeen 4- or 5-aminoindole carboxamides on the 2N4R isoform of tau. The selection of the best compounds was performed using alpha-synuclein (alpha-syn). The anti-oligomer and -fibril activities of newly synthesized aminoindole carboxamide derivatives were evaluated with biophys. methods, such as thioflavin T fluorescence assays, photo-induced crosslinking of unmodified proteins, and transmission electron microscopy. To evaluate the reduction of inclusions and cytoprotective effects, M17D neuroblastoma cells expressing inclusion-forming alpha-syn were treated with the best amide representatives. The 4-aminoindole carboxamide derivatives exhibited a better anti-fibrillar activity compared to their 5-aminoindole counterparts. The amide derivatives 2, 8, and 17 exerted anti-oligomer and anti-fibril activities on alpha-syn and the 2N4R isoform of tau. At a concentration of 40 μM, compound 8 reduced inclusion formation in M17D neuroblastoma cells expressing inclusion-prone alphaSynuclein3K::YFP. Our results demonstrate the potential of 4-aminoindole carboxamide derivatives with regard to inhibiting the oligomer formation of alpha-syn and tau (2N4R isoform) for further optimization prior to pre-clin. studies.

Keywords: Alzheimer's disease ; Amide ; Alpha-synuclein ; Fibril ; Oligomer

Purchased from AmBeed: 527-72-0 ; 5192-23-4 ; 586-38-9 ; 456-22-4 ; 5192-03-0 ; 6019-39-2 ; 153-78-6 ; 455-24-3 ; 182564-41-6 ; 708987-59-1

Targeting CTP synthetase 1 to restore interferon induction and impede nucleotide synthesis in SARS-CoV-2 infection

Rao, Youliang ; Wang, Ting-Yu ; Qin, Chao , et al. BioRxiv,2021. DOI: 10.1101/2021.02.05.429959 PubMed ID: 33564769

Abstract: The newly emerged SARS-CoV-2 caused a global pandemic with astonishing mortality and morbidity. The mechanisms underpinning its highly infectious nature remain poorly understood. We report here that SARS-CoV-2 exploits cellular CTP synthetase 1 (CTPS1) to promote CTP synthesis and suppress interferon (IFN) induction. Screening a SARS-CoV-2 expression library identified ORF7b and ORF8 that suppressed IFN induction via inducing the deamidation of interferon regulatory factor 3 (IRF3). Deamidated IRF3 fails to bind the promoters of classic IRF3-responsible genes, thus muting IFN induction. Conversely, a shRNA-mediated screen focused on cellular glutamine amidotransferases corroborated that CTPS1 deamidates IRF3 to inhibit IFN induction. Functionally, ORF7b and ORF8 activate CTPS1 to promote de novo CTP synthesis while shutting down IFN induction. De novo synthesis of small-molecule inhibitors of CTPS1 enabled CTP depletion and IFN induction in SARS-CoV-2 infection, thus impeding SARS-CoV-2 replication. Our work uncovers a strategy that a viral pathogen couples immune evasion to metabolic activation to fuel viral replication. Inhibition of the cellular CTPS1 offers an attractive means for developing antiviral therapy that would be resistant to SARS-CoV-2 mutation.

Purchased from AmBeed: 527-72-0

Product Details of [ 527-72-0 ]

CAS No. :	527-72-0	MDL No. :	MFCD00005437
Formula :	C₅H₄O₂S	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	QERYCTSHXKAMIS-UHFFFAOYSA-N
M.W :	128.15	Pubchem ID :	10700
Synonyms :

Calculated chemistry of [ 527-72-0 ] Expand+

Physicochemical Properties

Num. heavy atoms :	8
Num. arom. heavy atoms :	5
Fraction Csp3 :	0.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	31.28
TPSA :	65.54 Å²

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) :	-5.97 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.08
Log Po/w (XLOGP3) :	1.57
Log Po/w (WLOGP) :	1.45
Log Po/w (MLOGP) :	0.52
Log Po/w (SILICOS-IT) :	1.94
Consensus Log Po/w :	1.31

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.56

Water Solubility

Log S (ESOL) :	-2.02
Solubility :	1.22 mg/ml ; 0.00955 mol/l
Class :	Soluble
Log S (Ali) :	-2.56
Solubility :	0.356 mg/ml ; 0.00278 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-1.0
Solubility :	12.8 mg/ml ; 0.0998 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.72

Safety of [ 527-72-0 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 527-72-0 ]

* 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.

Upstream synthesis route of [ 527-72-0 ]
Downstream synthetic route of [ 527-72-0 ]

[ 527-72-0 ] Synthesis Path-Upstream 1~2

1
[ 527-72-0 ]
[ 75-65-0 ]
[ 56267-50-6 ]

Yield	Reaction Conditions	Operation in experiment
69%	for 5 h; Heating / reflux	A solution of thiophene2-carboxylic acid (1.00 g, 7.8 mmol), diphenylphosphoryl azide (2.15 g, 7.80 mmol) and triethylamine (1.1 mL, 7.8 mmol) in tert-butanol (20 mL) was heated at reflux for 5 hours, at which time thin layer chromatography (DCM/Hexanes) indicates the reaction is complete. The reaction mixture was cooled to room temperature, poured into water and extracted with diethyl ether (3.x.). The combined ether extracts were washed with brine, dried over anhydrous sodium sulfate, and then concentrated to afford a beige solid. Purification by column chromatography (SiO₂, DCM/Hexanes) afforded compound 113 as a white solid 1.07 g (69percent). ¹H-NMR (400 MHz, DMSO-d₆)δ 6.87(dd, 1H), 6.77 (m, 1H), 6.5 (dd, 1H), 1.46 (s, 9H).
69%	for 5 h; Heating / reflux	Example 113; A solution of thiophene2-carboxylic acid (1.00 g, 7.8 mmol), diphenylphosphoryl azide (2.15 g, 7.80 mmol) and triethylamine (1.1 mL, 7.8 mmol) in tert-butanol (20 mL) was heated at reflux for 5 hours, at which time thin layer chromatography (DCM/Hexanes) indicates the reaction is complete. The reaction mixture was cooled to room temperature, poured into water and extracted with diethyl ether (3.x.). The combined ether extracts were washed with brine, dried over anhydrous sodium sulfate, and then concentrated to afford a beige solid. Purification by column chromatography (SiO₂, DCM/Hexanes) afforded compound 113 as a white solid 1.07 g (69percent). ¹H-NMR (400 MHz, DMSO-d₆)δ 6.87 (dd, 1H), 6.77 (m, 1H), 6.5 (dd, 1H), 1.46 (s, 9H).
50%	at 90℃; for 4 h;	To a solution of thiophenecarboxylic acid (0.5 g, 3.90 mmol) in tBuOH (10 ml) was added Et₃N (0.571 ml, 4.10 mmol) and DPPA (0.883 ml, 4.10 mmol). The solution was heated at 90 °C for 4 hours. The reaction mixture was cooled to RT and the solvent was removed in vacuo. The residue was treated with benzene and then the solution was washed with 5percent citric acid, and sat'd NaHCO₃. Solid was filtered off and the filtrate was washed with brine. The organic layer was dried (MgSO₄), concentrated in vacuo and the residue was purified by silica gel column chromatography (EtOAc/hexanes) to obtain tert-butyl thiophen-2-ylcarbamate (0.39 g, 50percent yield). ¹H NMR (400 MHz, DMSO-d₆): δ 10.4 (brs, 1H), 6.84 (dd, J = 1.6, and 5.2 Hz, 1H), 6.75 (dd, J = 4.0, and 5.6 Hz, 1H), 6.48 (dd, J= 1.6, and 4.0 Hz, 2H), 1.45 (s, 9H); MS (ESI) m/z: 222.0 (M+22+H⁺).

Reference： [1] Journal of Medicinal Chemistry, 1991, vol. 34, # 5, p. 1594 - 1605
[2] Patent: US2007/105864, 2007, A1, . Location in patent: Page/Page column 151
[3] Patent: US2007/117804, 2007, A1, . Location in patent: Page/Page column 77
[4] Journal of Medicinal Chemistry, 2002, vol. 45, # 20, p. 4513 - 4523
[5] Journal of Medicinal Chemistry, 2007, vol. 50, # 20, p. 4898 - 4908
[6] Patent: WO2010/51373, 2010, A1, . Location in patent: Page/Page column 100
[7] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 21, p. 5567 - 5571

2
[ 527-72-0 ]
[ 112887-68-0 ]

Reference： [1] Patent: CN107616976, 2018, A,
[2] Patent: CN107616976, 2018, A,

[ 527-72-0 ] Synthesis Path-Downstream 1~8

1
[ 188290-36-0 ]
[ 527-72-0 ]
[ 704-38-1 ]

Reference： [1]Journal of the American Chemical Society,1947,vol. 69,p. 3098
[2]Journal of the Chemical Society,1956,p. 698,703

2
[ 527-72-0 ]
[ 19418-11-2 ]
(+)-3-Hydroxytetrahydrothiophene-2-carboxylic acid [ No CAS ]

Reference： [1]Agricultural and Biological Chemistry,1982,vol. 46,p. 1429 - 1438
[2]Agricultural and Biological Chemistry,1982,vol. 46,p. 1429 - 1438

3
[ 527-72-0 ]
[ 57772-50-6 ]
HO-(2,6-naphthylidene)-C(NH)NHC(O)OCH₂-(p-C₆H₄)-OCH₂C(O)NHCH₂-(polystyrene resin) [ No CAS ]
N₂-2-[(6-[amino(imino)methyl]-2-naphthyloxy)methyl]-6-methylphenyl-2-thiophenecarboxamide [ No CAS ]

Reference： [1]Tetrahedron,1999,vol. 55,p. 6219 - 6230

4
[ 527-72-0 ]
amberlyst-15 [ No CAS ]
[ 704-38-1 ]

Yield	Reaction Conditions	Operation in experiment
8 g (41.6%)	With trifluoroacetic acid; In thiophene; nitromethane;	(a) To a mixture of 12.7 g (0.099 mol) of 2-thienylcarboxylic acid, 8.33 g (0.099 mol) of thiophene, and 34.9 ml of Amberlyst-15 in 250 ml of nitromethane was added 34.9 ml (0.247 mol) of trifluoroacetic acid at room temperature and stirred for 14 h. The reaction mixture was filtered, the filtrate was concentrated in vacuo, and a green oil residue was chromatographed on silica (hexane/methylene chloride 1:1) to afford 8 g (41.6%) of di-(2-thienyl)ketone, as white needles.
8 g (41.6%)	With trifluoroacetic acid; In thiophene; nitromethane;	(a) To a mixture of 12.7 g (0.099 mol) of 2-thienylcarboxylic acid, 8.33 g (0.099 mol) of thiophene, and 34.9 mL of Amberlyst-15 in 250 mL of nitromethane was added 34.9 mL (0.247 mol) of trifluoroacetic acid at room temperature and stirred for 14 h. The reaction mixture was filtered, the filtrate was concentrated in vacuo, and a green oil residue was chromatographed on silica (hexane/methylene chloride 1:1) to afford 8 g (41.6%) of di-(2-thienyl)ketone, as white needles.

Reference： [1]Patent: US5569655,1996,A
[2]Patent: US5554620,1996,A

5
[ 19498-72-7 ]
[ 527-72-0 ]
[ 5928-51-8 ]

Reference： [1]ChemSusChem,2016,vol. 9,p. 241 - 245

6
[ 527-72-0 ]
[ 704-38-1 ]

Reference： [1]Journal of Organic Chemistry,2016,vol. 81,p. 2987 - 2992

7
[ 527-72-0 ]
[ 35418-07-6 ]
C₁₅H₁₅NO₃S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		General procedure: To a solution of 3a (1 g) in ethanol was added Pd/C (5%, 0.1 g) and the mixture was stirred for 24 hrs at room temperature in a hydrogen atmosphere under atmospheric pressure. Insoluble matters were removed using Celite, and the filtrate was concentrated in vacuo to give the desired product 4a (0.76 g) as a yellow solid. To a solution of carboxylic acid (1 equiv) in CH2Cl2 (15 mL) at 0 C was added DMAP (1 equiv) and EDCI (1 equiv). The reaction mixture was stirred at 0 C for 45 minutes. At this time 4a (1 equiv) was added and the mixture was warmed to room temperature and stirred overnight. The resulting mixture was concentrated in vacuo, partitioned between 1.0 M HCl (20 ml) and ethyl acetate (3×20 mL). The combined organic layers were washed with brine (2 × 15 ml), dried over Na2SO4, filtered and concentrated in vacuo. The crude residue was purified by silica gel chromatograph using a mixture of petroleum ether/ethyl acetate (20 : 5, v/v) as eluent to afford the product as a white solid. To a solution of the obtained solid (1 equiv) in 2:3:1 THF/MeOH/H2O (18 ml) was added LiOH·H2O (1.5 equiv). After stirring at room temperature for 4 h, the volatiles were removed under reduced pressure. The residue was acidified with 1N hydrochloric acid solution, and then filtered and the filter cake was washed with 5 mL of water, dried in vacuum to afford a white powder. Recrystallization from 75% EtOH gave the desired compounds 2-17 as white solid.

Reference： [1]Bioorganic and Medicinal Chemistry,2017,vol. 25,p. 2445 - 2450

8
[ 4565-31-5 ]
[ 527-72-0 ]

Reference： [1]Organic Letters,2019

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Isomers

Technical Information

• Arndt-Eistert Homologation • Hunsdiecker-Borodin Reaction • Passerini Reaction • Preparation of Amines • Preparation of Carboxylic Acids • Reactions of Amines • Reactions of Carboxylic Acids • Schmidt Reaction • Specialized Acylation Reagents-Ketenes • Ugi Reaction

Historical Records

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[ 527-72-0 ]

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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

[ CAS No. 527-72-0 ] {[proInfo.proName]}

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