Stereoselective synthesis and antibacterial evaluation of 4-amido-isothiazolidinone oxides.
Two well-defined oxidative chlorination-cyclization processes have been developed for the stereoselective synthesis of a variety of 4-amido-isothiazolidinone oxide derivatives. The stereochemistry of the cyclization products was confirmed by X-ray crystallography. These new compounds were designed as bacterial serine protease inhibitors. In tests, some of them showed weak antibacterial activity.
Chen
Z
Z
Procter & Gamble Pharmaceuticals, 8700Mason-Montgomery Road, Mason, OH 45040, USA. chen.jz@pg.com
Demuth
T P
TP
Wireko
F C
FC
D000577:Amides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D002713:Chlorine / Q000737:chemistry; D003500:Cyclization; D016972:Enterobacter cloacae / Q000187:drug effects; D007711:Klebsiella pneumoniae / Q000187:drug effects; D008826:Microbial Sensitivity Tests; D008968:Molecular Conformation; D001936:Moraxella catarrhalis / Q000187:drug effects; D013844:Thiazoles / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology
D000577:Amides; D000900:Anti-Bacterial Agents; D013844:Thiazoles; D002713:Chlorine