69570-39-4

Basic information

• Product Name: S-(3-chloro-2-methyl-3-oxopropyl) (S)-ethanethioate
• Synonyms: S-(3-chloro-2-methyl-3-oxopropyl) (S)-ethanethioate;(S)-3-Acetylthio-2-methylpropionyl chloride;Ethanethioic acid S-[(S)-3-chloro-2-methyl-3-oxopropyl] ester;Captopril Related Compound 6
• CAS NO: 69570-39-4
• Molecular Formula: C₆H₉ClO₂S
• Molecular Weight: 180.65246
• EINECS: 274-044-6
• Mol File: 69570-39-4.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 229.078°C at 760 mmHg
• Flash Point: 92.344°C
• Appearance: /
• Density: 1.224g/cm³
• Vapor Pressure: 0.071mmHg at 25°C
• Refractive Index: 1.491
• CAS DataBase Reference: S-(3-chloro-2-methyl-3-oxopropyl) (S)-ethanethioate(CAS DataBase Reference)
• NIST Chemistry Reference: S-(3-chloro-2-methyl-3-oxopropyl) (S)-ethanethioate(69570-39-4)
• EPA Substance Registry System: S-(3-chloro-2-methyl-3-oxopropyl) (S)-ethanethioate(69570-39-4)

Safety Data

• Hazardous Substances Data: 69570-39-4(Hazardous Substances Data)

Usage

General Description

"S-(3-chloro-2-methyl-3-oxopropyl) (S)-ethanethioate" is a chemical compound that is commonly used in organic synthesis and pharmaceutical research. It is a thioester derivative of 3-chloro-2-methyl-3-oxopropyl and ethanethioate, and is often used as a building block in the production of various pharmaceutical and agrochemical compounds. S-(3-chloro-2-methyl-3-oxopropyl) (S)-ethanethioate has potential use as a chiral building block for the synthesis of various bioactive molecules and pharmaceutical intermediates. It is important to handle this chemical with care and use proper safety precautions, as it can be hazardous if not handled properly.

InChI:InChI=1/C6H9ClO2S/c1-4(6(7)9)3-10-5(2)8/h4H,3H2,1-2H3/t4-/m0/s1

Upstream product

• 74431-52-0 (R)-3-acetylsulfanyl-2-methyl-propionic acid 
• 76497-39-7 (2S)-3-acetylthio-2-methylpropionic acid 

Downstream Products

• 224626-08-8 (R)-1-((R)-3-Acetylsulfanyl-2-methyl-propionyl)-pyrrolidine-2-carboxylic acid 
• 65167-28-4 (2S)-1-((2R)-3-(acetylthio)-2-methylpropanoyl)pyrrolidine-2-carboxylic acid 
• 77708-84-0 N-(3'-Acetylthio-2'-methylpropanoyl)-L-(1,2,3,4-tetrahydroisoquinoline)-3-carboxylic acid 
• 77708-84-0 (S)-2-(3-Acetylsulfanyl-2-methyl-propionyl)-1,2,3,4-tetrahydro-isoquinoline-3-carboxylic acid 
• 86323-70-8 [((S)-3-Acetylsulfanyl-2-methyl-propionyl)-(3,4-dimethoxy-phenyl)-amino]-acetic acid ethyl ester 

Relevant articles and documents

Structural basis of metallo-β-lactamase inhibition by captopril stereoisomers

β-Lactams are the most successful antibacterials, but their effectiveness is threatened by resistance, most importantly by production of serine- and metallo-β-lactamases (MBLs). MBLs are of increasing concern because they catalyze the hydrolysis of almost all β-lactam antibiotics, including recent-generation carbapenems. Clinically useful serine-β-lactamase inhibitors have been developed, but such inhibitors are not available for MBLs. L-Captopril, which is used to treat hypertension via angiotensin-converting enzyme inhibition, has been reported to inhibit MBLs by chelating the active site zinc ions via its thiol(ate). We report systematic studies on B1 MBL inhibition by all four captopril stereoisomers. High-resolution crystal structures of three MBLs (IMP-1, BcII, and VIM-2) in complex with either the L- or D-captopril stereoisomer reveal correlations between the binding mode and inhibition potency. The results will be useful in the design of MBL inhibitors with the breadth of selectivity required for clinical application against carbapenem-resistant Enterobacteriaceae and other organisms causing MBL-mediated resistant infections.

Angiotensin-Converting Enzyme Inhibitors. New Orally Active Antihypertensive (Mercaptoalkanoyl)- and glycine Derivatives

A variety of N-substituted (mercaptoalkanoyl)- and glycine derivatives was synthesized and their ability in inhibiting the activity of angiotensin-converting enzyme (ACE) was examined in vitro and in vivo.The acylthio derivatives prepared are assumed to act as prodrugs since they are much less active than the corresponding free SH compounds in vitro and can be expected to act in vivo only after conversion to the free sulfhydryl compounds.A number of this compounds are potent ACE inhibitors that lowered blood pressure in Na-deficient, conscious spontaneously hypertensive rats (SHR), a high renin model.One of the most active members of the series was (S)-N-cyclopentyl-N--2-methyl-1-oxopropyl>glycine (REV 3659-(S), pivopril).Structure-activity relationships are discussed.