Syntheses and Antimicrobial Activities of Five-Membered Heterocycles Having a Phenylazo Substituent

• Published in: Chemical & pharmaceutical bulletin Vol. 32; no. 8; pp. 3291 - 3298
• Main Authors: TANAKA, KUNIYOSHI, MATSUO, KEIZO, NAKANISHI, AI, JO, MISAKO, SHIOTA, HIRONORI, YAMAGUCHI, MIKIKO, YOSHINO, SAKIKO, KAWAGUCHI, KEIKO
• Format: Journal Article
• Language: English
• Published: Tokyo The Pharmaceutical Society of Japan 1984; Maruzen
• Subjects: Anti-Infective Agents - chemical synthesis; antimicrobial activity; Azo Compounds - chemical synthesis; Azo Compounds - pharmacology; Chemical Phenomena; Chemistry; Exact sciences and technology; Heterocyclic compounds; Heterocyclic Compounds - chemical synthesis; Heterocyclic Compounds - pharmacology; Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms; Organic chemistry; Preparations and properties; Azo compound; Sulfur nitrogen heterocycle; Five membered ring; Nitrogen heterocycle; Enol; Lactam; Azo hydrazono tautomerism; Lactone; Oxygen heterocycle; Biological activity; Antimicrobial agent; Oxygen nitrogen heterocycle
• ISSN: 0009-2363; 1347-5223
• DOI: 10.1248/cpb.32.3291

Several five-membered heterocycles having a phenylazo substituent, 3-phenylazotetronic acids (2a-n), 3-phenylazotetramic acids (4a-i), 4-phenylazo-5-isoxazolinones (6a-g, 8a-f) and 5-phenylazo-4-thiazolidinones (10a-f, 12a-e), were synthesized and tested for antimicrobial activities. Tetronic acid and tetramic acid derivatives (2 and 4) inhibited the growth of gram-positive bacteria. 5-Isoxazolinone and 4-thiazolidinone derivatives (8 and 10) showed inhibitory activities against fungi as well as bacteria.