70491-03-1

Basic information

• Product Name: L-Proline, 1-(2-mercaptobenzoyl)-
• CAS NO: 70491-03-1
• Molecular Formula: C12H13NO3S
• Molecular Weight: 251.306
• Mol File: 70491-03-1.mol

Chemical Properties

• CAS DataBase Reference: L-Proline, 1-(2-mercaptobenzoyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: L-Proline, 1-(2-mercaptobenzoyl)-(70491-03-1)
• EPA Substance Registry System: L-Proline, 1-(2-mercaptobenzoyl)-(70491-03-1)

Safety Data

• Hazardous Substances Data: 70491-03-1(Hazardous Substances Data)

Upstream product

• 147-93-3 Thiosalicylic acid 
• 3724-10-5 2-(methylthio)benzoic acid 
• 147-85-3 L-proline 
• 121451-36-3 N-(2-methylsulphinylbenzoyl)-L-proline t-butyl ester 
• 1442-03-1 2-methylsulfanyl-benzoyl chloride 
• 121451-34-1 N-(2-methylthiobenzoyl)-L-proline t-butyl ester 
• 121451-35-2 N-(2-methylthiobenzoyl)-L-proline 
• 2812-46-6 proline tert-butyl ester 
• 19602-82-5 2,2'-dithiodibenzoic acid dichloride 
• 55819-78-8 2-acetylmercaptobenzoic acid 
• 92420-29-6 (S)-methyl 1-(2-(acetylthio)benzoyl)pyrrolidine-2-carboxylate 
• 121451-38-5 [S-(R*,R*)]-1,1'-[Dithiobis(2,1-phenylenecarbonyl)]bis-1H-pyrrolidine-2-carboxylic acid 
• 121451-37-4 N-(2-mercaptobenzoyl)-L-proline t-butyl 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. (Mercaptoaroyl)amino acids

A series of (mercaptoaroyl)amino acids and related compounds was synthesized and tested for ability to inhibit angiotensin converting enzyme (ACE). The most active compound was N-(3-chloro-2-mercaptobenzoyl)-N-cyclo-pentylglycine, having an in vitro I50 = 0.28 μM. Substitution of the aromatic 3-position by small polar groups enhanced ACE inhibitory activity, whereas bulky groups diminished it. Alteration of the β relationship between the mercaptan and amide carbonyl or masking of the thiol by acylation reduced activity. Replacement of the thiol by nitro, hydroxy, or carboxy gave compounds lacking ACE inhibitory activity.