78779-29-0

Basic information

• Product Name: (2S)-1-[(2S)-2-methyl-3-sulfanylpropanoyl]-2,3-dihydro-1H-indole-2-carboxylic acid
• Synonyms: Wy 44221;(2S)-2,3-Dihydro-1-[(S)-3-mercapto-2-methyl-1-oxopropyl]-1H-indole-2α-carboxylic acid
• CAS NO: 78779-29-0
• Molecular Formula: C₁₃H₁₅NO₃S
• Molecular Weight: 265.3281
• Mol File: 78779-29-0.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 538.6°C at 760 mmHg
• Flash Point: 279.5°C
• Density: 1.323g/cm³
• Vapor Pressure: 1.97E-12mmHg at 25°C
• Refractive Index: 1.613
• CAS DataBase Reference: (2S)-1-[(2S)-2-methyl-3-sulfanylpropanoyl]-2,3-dihydro-1H-indole-2-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (2S)-1-[(2S)-2-methyl-3-sulfanylpropanoyl]-2,3-dihydro-1H-indole-2-carboxylic acid(78779-29-0)
• EPA Substance Registry System: (2S)-1-[(2S)-2-methyl-3-sulfanylpropanoyl]-2,3-dihydro-1H-indole-2-carboxylic acid(78779-29-0)

Safety Data

• Hazardous Substances Data: 78779-29-0(Hazardous Substances Data)

Upstream product

• 86323-74-2 ethyl 1-<3-(benzoylthio)-2(S)-methylpropionyl>indoline-2(S)-carboxylate 
• 82923-81-7 (S)-2,3-dihydro-1H-indole-2-carboxylic acid ethyl ester 
• 78701-25-4 (S)-1-<3-(benzoylthio)-2-methyl-1-oxopropyl>indoline-2-carboxylic acid 
• 78701-38-9 (-)-1-(2-methyl-1-oxo-2-propenyl)indoline-2-carboxylic acid 
• 78701-24-3 2,3-Dihydro-1-(2-methyl-1-oxo-2-propenyl)-1H-indole-2-carboxylic acid 
• 78701-23-2 2,3-dihydro-1-(2-methyl-1-oxo-2-propenyl)-1H-indole-2-carboxylic acid ethyl ester 
• 50501-07-0 (S)-2,3-dihydro-1H-indole-2-carboxylic acid,ethyl ester 
• 16851-56-2 indolin-2-yl carboxylic acid 
• 78779-25-6 Wy-44,088 
• 86324-49-4 ethyl 1-<3-mercapto-2(S)-methylpropionyl>indoline-2(S)-carboxylate 

Downstream Products

• 79815-20-6 (S)-indoline-2-carboxylic acid 
• 27640-33-1 (2S)-2,3-dihydro-1H-indole-2-ylmethanol 

Relevant articles and documents

1-mercaptoalkanoylindoline-2-carboxylic acids

1-Mercaptoalkanoylindoline-2-carboxylic acids, e.g., those of the formula STR1 and functional derivatives thereof, are antihypertensive and cardioactive agents.

(Mercaptopropanoyl)indoline-2-carboxylic Acids and Related Compounds as Potent Angiotensin Converting Enzyme Inhibitors and Antihypertensive Agents

1-(3-Mercapto-2-methyl-1-oxopropyl)indoline-2-carboxylic acids (7b) and related compounds were synthesized in order to examine their ability to inhibit angiotensin converting enzyme (ACE) and to reduce the systolic blood pressure of spontaneously hypertensive rats (SHR).All four possible stereoisomers of the precursor 1-indoline-2-carboxylic acid (6b) were characterized with absolute stereochemical assigment.The removal of the benzoyl group of the precursor to give 7b was conveniently carried out by treatment with 2-methoxyethylamine.Three of the four stereoisomers of the benzoyl derivative 6 showed in vitro ACE inhibitory activity in the following order: 6b(S,S) > 6b(S,R) > 6b(R,S).The stereoisomer having the R,R configuration was essentialy inactive.The substitution at the C5 of the indoline nucleus with the Et or OMe group caused only marginal changes in the inhibitory activity.The mercaptan 7b(S,S) was the most active ACE inhibitor synthesized in this study, showing in vitro potency 3 times that of captopril.The augmentation of the potency may be due to the increased hydrophobicity of 7b (S,S) compared with captopril and suggests the presence of a hydrophobic pocket at the active site of ACE.When tested in spontaneously hypertensive rats, 7b(S,S) exhibited oral antihypertensive activity 27 times that of captopril.The corresponding benzoyl derivative 6b(S,S) was 24 times as potent as captopril.The thio lactone 10 obtained by cyclization of 7b(S,S) as a potential prodrug was less potent than the parent compound, 7b(S,S), in the ACE inhibitory and antihypertensive tests.

N-(2-SUBSTITUTED-1-OXOALKYL)-2,3-DIHYDRO-1H-INDOLE-2-CARBOXYLIC ACID DERIVATIVES

Disclosed herein are 2,3-dihydro-1H-indole-2-carboxylic acids substituted on the nitrogen with 3-mercapto-2-alkyl-1-oxoalkyl, 3-phosphoryl-2-alkyl-1-oxopropyl, or 2-amino-2-alkyl-1-oxoalkyl derivatives which act as inhibitors of angiotensin converting enz