63250-36-2

Usage

Uses

Used in Pharmaceutical Industry:
1-[(2R)-2-Methyl-3-mercaptopropionyl]proline is used as an impurity in the synthesis of Captopril, an ACE inhibitor, for the treatment of hypertension and congestive heart failure. Its presence in the final product is closely monitored and controlled to ensure the safety and efficacy of the medication.
Used in Quality Control and Research:
1-[(2R)-2-Methyl-3-mercaptopropionyl]proline serves as a reference compound in the development of analytical methods for the detection and quantification of impurities in Captopril. This is crucial for maintaining the quality and purity of the drug, as well as for advancing research in the field of pharmaceutical chemistry.
Used in Drug Development:
As an impurity derived from the synthesis of Captopril, 1-[(2R)-2-Methyl-3-mercaptopropionyl]proline may also be used in the development of new drugs with similar mechanisms of action or improved properties. Understanding the structure and properties of 1-[(2R)-2-Methyl-3-mercaptopropionyl]proline can contribute to the design of novel therapeutic agents for the treatment of cardiovascular diseases.

Upstream product

• 78825-16-8 1-(3-mercapto-2-D-methyl-1-oxopropyl)-L-proline 
• 7440-66-6 zinc 
• 65167-28-4 (2S)-1-((2R)-3-(acetylthio)-2-methylpropanoyl)pyrrolidine-2-carboxylic acid 

Downstream Products

• 460-19-5 ethanedinitrile 
• 75479-46-8 (S)-1-[3-((R)-2-Amino-2-carboxy-ethyldisulfanyl)-2-methyl-propionyl]-pyrrolidine-2-carboxylic acid 
• 78636-28-9 (S)-1-(3-Methanesulfinyl-2-methyl-propionyl)-pyrrolidine-2-carboxylic acid 
• 78636-29-0 (S)-1-(2-Methyl-3-methylsulfanyl-propionyl)-pyrrolidine-2-carboxylic acid 
• 77083-32-0 (S)-1-{3-[2-(4-Bromo-phenyl)-2-oxo-ethylsulfanyl]-2-methyl-propionyl}-pyrrolidine-2-carboxylic acid 
• 128960-77-0 glutathione 
• 64838-57-9 captopril disulfide 
• 78636-30-3 captopril-glutathione mixed disulfide 
• 77083-33-1 (S)-1-{3-[1-(4-Dimethylamino-3,5-dinitro-phenyl)-2,5-dioxo-pyrrolidin-3-ylsulfanyl]-2-methyl-propionyl}-pyrrolidine-2-carboxylic acid 

Relevant academic research and scientific papers

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.

Process for preparation of optically active N-mercaptoalkanoylamino acids

A process is disclosed wherein an optically active N-mercaptoalkanoylamino acid is prepared by (1) reacting an optically active β-hydroxyalkanoic acid, with a halogenating reagent to prepare an optically active β-haloalkanoyl halide (2) reacting the β-haloalkanoyl halide with an amino acid to produce an optically active N-β-haloalkanoylamino acid and (3) reacting the N-β-haloalkanoylamino acid with a reagent capable of converting the halogen into the thiol group, the configuration of the formulas (II), (III), (IV), (V), and (VI) being retained in all the optically active compounds throughout the process to prepare the compound represented by formula (I). The product of the present invention, for example, N-(3-mercapto-2-D-methylpropanoyl)-L-proline inhibits the enzymatic conversion of angiotensin I into angiotensin II and therefore is useful for relieving angiotensin-related hypertension.

Pyridinium salts

The invention concerns compounds of formula STR1 wherein the sulphur is bonded to the pyridinium ring at position 2 or 4, Y is --S-- or --CH2 --, R represents hydrogen, or a lower alkyl group, or other carboxylic protecting group; R1 represents hydrogen or lower alkyl; R2 represents lower alkyl, aryl of 6 to 10 carbon atoms or aralkyl of 7 to 11 carbon atoms; R3 represents hydrogen or a substituent selected from lower alkyl, halogen and lower alkoxy; q and r are each 1 or 2; and X? represents a halide ion or an organosulphonate ion, which are antihypertensive agents and are useful as intermediates to captopril and analogous compounds.

PROLINE DERIVATIVES AND RELATED COMPOUNDS

New proline derivatives and related compounds which have the general formula STR1 are useful as angiotensin converting enzyme inhibitors.