Synthesis and antibacterial activity of 1β-methyl-2-[5-( N-substituted-2-hydroxy iminoethyl)pyrrolidin-3-ylthio]carbapenem derivatives

• Published in: European journal of medicinal chemistry Vol. 38; no. 7; pp. 751 - 758
• Main Authors: Oh, Chang-Hyun, Lee, Su-Chul, Cho, Jung-Hyuck
• Format: Journal Article
• Language: English
• Published: ISSY-LES-MOULINEAUX Elsevier Masson SAS 01.07.2003; Elsevier
• Subjects: 1β-Methylcarbapenem; Antibacterial agents; Antibiotics. Antiinfectious agents. Antiparasitic agents; Biological and medical sciences; Chemistry, Medicinal; Life Sciences & Biomedicine; Medical sciences; Pharmacology & Pharmacy; Pharmacology. Drug treatments; Science & Technology; β-Lactam antibiotics; β-Lactam antibiotics; 1β-Methylcarbapenem; 1 beta-methylcarbapenem; beta-lactam antibiotics; CARBAPENEM; Pseudomonadales; Angular nitrogen heterocycle; Lactam; Alcohol; In vitro; Pyrrolidine derivatives; Organic sulfide; Penicillin derivatives; Carbapenem derivatives; Structure activity relation; Gram positive bacteria; Amidoxime; Bacteria; Pseudomonadaceae; Pseudomonas aeruginosa; Piperazine derivatives; Antibacterial agent; Chemical synthesis; Gram negative bacteria
• ISSN: 0223-5234; 1768-3254
• DOI: 10.1016/S0223-5234(03)00116-8

The synthesis of a new series of 1-methylcarbapenems having the substituted thiazolopyrrolidine moiety is described. Their in vitro antibacterial activities against both gram-positive and gram-negative bacteria were tested and the effect of substituent on the pyrrolidine ring was investigated. In particular, compounds 12b and 12k showed the most potent antibacterial activity.