64838-55-7

Basic information

• Product Name: (2S)-1-(3-Acetylthio-2-methyl-1-oxopropyl)-L-proline
• Synonyms: N-[3-(ACETYLTHIO)-(2S)-METHYL-1-OXOPROPYL]-L-PROLINE HYDRATE;n-[3-(acetylthio)-(2s)-methylpropionyl]-l-proline;N-[3-(ACETYLTHIO)-(2S)-METHYLPROPYL]-L-PROLINE HYDRATE;(S)-3-ACETYLTHIO-2-METHYLPROPIONYL-L-PROLINE;1-[(2S)-3-(ACETYLTHIO)-2-METHYL-1-OXOPROPYL]-L-PROLINE HYDRATE;1-[(2S)-3-(ACETYLTHIO)-2-METHYLPROPIONYL]-L-PROLINE;1-[(2S)-3-(ACETYLTHIO)-2-METHYLPROPIONYL]-L-PROLINE HYDRATE;(2s)-1-(3-acetylthio-2-methyl-1-oxopropyl)-l-proline
• CAS NO: 64838-55-7
• Molecular Formula: C₁₁H₁₇NO₄S
• Molecular Weight: 259.32
• EINECS: 265-250-7
• Product Categories: Sulphur Derivatives;(intermediate of captopril);Peptide Synthesis;Proline Derivatives;Unnatural Amino Acid Derivatives
• Mol File: 64838-55-7.mol
• Article Data: 7

Chemical Properties

• Melting Point: 76-82 °C(lit.)
• Boiling Point: 464.8 °C at 760 mmHg
• Flash Point: 234.9 °C
• Appearance: /
• Density: 1.291 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: -160 ° (C=1, MeOH)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 3.56±0.20(Predicted)
• CAS DataBase Reference: (2S)-1-(3-Acetylthio-2-methyl-1-oxopropyl)-L-proline(CAS DataBase Reference)
• NIST Chemistry Reference: (2S)-1-(3-Acetylthio-2-methyl-1-oxopropyl)-L-proline(64838-55-7)
• EPA Substance Registry System: (2S)-1-(3-Acetylthio-2-methyl-1-oxopropyl)-L-proline(64838-55-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36
• Safety Statements: 24/25-26
• WGK Germany: 3
• Hazardous Substances Data: 64838-55-7(Hazardous Substances Data)

Usage

Chemical Properties

white fine powder

Uses

(2S)-1-(3-Acetylthio-2-methyl-1-oxopropyl)-L-proline is used in the preparation of captopril derivatives, used as angiotensin converting enzymes.

InChI:InChI=1/C11H17NO4S/c1-7(6-17-8(2)13)10(14)12-5-3-4-9(12)11(15)16/h7,9H,3-6H2,1-2H3,(H,15,16)/t7?,9-/m0/s1

Upstream product

• 62571-86-2 captopril 
• 75-36-5 acetyl chloride 
• 65167-28-4 (2S)-1-((2R)-3-(acetylthio)-2-methylpropanoyl)pyrrolidine-2-carboxylic acid 
• 74345-73-6 (2R,S)-3-Acetylthio-2-methylpropanoyl chloride 
• 147-85-3 L-proline 
• 51161-88-7 N-methacryloyl-L-proline 
• 507-09-5 tiolacetic acid 

Downstream Products

• 74258-91-6 1-((S)-3-acetylthio-2-methylpropanoyl)-L-prolyl-L-phenylalanine ethyl ester 
• 62571-86-2 captopril 
• 74258-85-8 1-[(2S)-3-(acetylthio)-2-methyl-1-oxopropyl]-L-prolyl-L-phenylalanine tert-butyl ester 

Relevant articles and documents

In silico design, synthesis, characterization and pharmacological evaluation of captopril conjugates in the treatment of renal fibrosis

Renal fibrosis is a renal disorder whereby production of excess fibrous connective tissue in the glomerulus and proximal convoluted tubules will occur in a reparative or reactive process leading to severe conditions like surgery, replacement, etc. Such a condition needs pharmacotherapy with drugs reducing renal overload (captopril) and inflammation (taurine). In this research project, two chemical conjugates of captopril with taurine and glutamic acid were developed using in silico analysis for an improvement in bioavailability with a reduction in inflammation. The stability of these conjugates in sheep kidney cells and in human plasma along with transport across renal cells was investigated using in vitro protocols. The results of these studies have revealed that conjugates have retained desired interactions for transportability across renal epithelial cells and their bioactivity against ACE and TGF-β. Both conjugates A and B were found to be stable over a period of 14 h in plasma and transported nearly 2 times more than captopril across renal epithelial cells. These conjugates were almost entirely hydrolyzed in renal lysosomes over a period of 14 h (87.39 ± 2.59%). Thus a combination of these two conjugates would be an effective chemotherapy to prevent progression of renal fibrosis to renal failure after in vivo studies of these conjugates.

Tetrahydroisoquinoline derivative and application thereof

The invention belongs to the technical field of medicines, relates to a 2-{(2s)-1-[(2S)-3-ethanethioate-2-methyl propionyl] pyrrolidine-2-formamido}-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid methyl ester derivative and an application thereof, and in particular relates to a stereomer and a pharmaceutically acceptable salt of the compound. The general structural formula is as shown in the specification. The 2-{(2s)-1-[(2S)-3-ethanethioate-2-methyl propionyl] pyrrolidine-2-formamido}-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid methyl ester compound as well as pharmaceutically acceptable acid and additive salt of the compound can be combined with an existing medicine and can be individually used as an angiotensin-converting enzyme inhibitor to be applied to treatment of hypertension. Compared with the prior art, 6,7,8 side chains of a tetrahydroisoquinoline ring are obviously changed; the inhibition rate of the sample on angiotensin-converting enzyme is significantly improved; and the tetrahydroisoquinoline derivative has good application values and development and application prospects.

Synthesis and characterization of captopril derivatives

To develop more potential angiotensin converting enzyme (ACE) inhibitors, a series of captopril (Cap) derivatives were synthesized, including Cap-glycine methyl ester, Cap-l-alanine methyl ester, Cap-l-aspartic acid dimethyl ester, Cap-l-lysine methyl ester, Cap-O-acylisourea, acetyl captopril, and benzoyl captopril. The resulting products were characterized by IR and UV-visible spectroscopy and MS, which showed the desired products were successfully synthesized. This could serve as a guide for rational design of highly potent ACE inhibitors.