63250-36-2Relevant articles and documents
Structural basis of metallo-β-lactamase inhibition by captopril stereoisomers
Brem, Jürgen,Van Berkel, Sander S.,Zollman, David,Lee, Sook Y.,Gileadi, Opher,McHugh, Peter J.,Walsh, Timothy R.,McDonough, Michael A.,Schofield, Christopher J.
supporting information, p. 142 - 150 (2016/02/19)
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.
Pyridinium salts
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, (2008/06/13)
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
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, (2008/06/13)
New proline derivatives and related compounds which have the general formula STR1 are useful as angiotensin converting enzyme inhibitors.