SYNTHESIS AND ANTIMICROBIAL ACTIVITY OF CEPHALOSPORINS WITH A 1-PYRIDINIUM SUBSTITUENT CARRYING A 5-MEMBERED HETEROCYCLE AT THE C-3 POSITION

• Published in: Journal of antibiotics Vol. 40; no. 1; pp. 43 - 48
• Main Authors: EJIMA, AKIO, HAYANO, TAKESHI, EBATA, TSUTOMU, NAGAHARA, TAKAYASU, KODA, HIROKO, TAGAWA, HIROAKI, FURUKAWA, MINORU
• Format: Journal Article
• Language: English
• Published: Tokyo JAPAN ANTIBIOTICS RESEARCH ASSOCIATION 01.01.1987; Japan Antibiotics Research Association
• Subjects: Cephalosporins - chemical synthesis; Cephalosporins - pharmacology; Chemistry; Exact sciences and technology; Gram-Negative Bacteria - drug effects; Gram-Positive Bacteria - drug effects; Heterocyclic compounds; Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms; Indicators and Reagents; Microbial Sensitivity Tests; Organic chemistry; Preparations and properties; Pyridinium Compounds - chemical synthesis; Pyridinium Compounds - pharmacology; Structure-Activity Relationship; Sulfur nitrogen heterocycle; Antibiotic; Five membered ring; Nitrogen heterocycle; Preparation; Bicyclic compound; Antibacterial agent; Biological activity; Physicochemical properties
• ISSN: 0021-8820; 1881-1469
• DOI: 10.7164/antibiotics.40.43

A series of potent antimicrobial agents have been prepared. These derivatives are cephalosporins carrying a pyridine ring substituted with a heterocycle in the C-3 position. Some of them showed excellent activity not only against Gram-negative organisms including Pseudomonas aeruginosa but also against Gram-positive ones. In view of their biological and physico-chemical properties, 7β-[2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido]-3-[4-(2 or 5-oxazolyl)-1-pyridinium]methyl-3-cephem-4-carboxylate 8f (DQ-2522) and 8g (DQ-2556) were chosen as candidates for further evaluation.