Heterocyclic benzazole derivatives with antimycobacterial In vitro activity

• Published in: Bioorganic & medicinal chemistry letters Vol. 12; no. 22; pp. 3275 - 3278
• Main Authors: Kočı́, Jan, Klimešová, Věra, Waisser, Karel, Kaustová, Jarmila, Dahse, Hans-Martin, Möllmann, Ute
• Format: Journal Article
• Language: English
• Published: Oxford Elsevier Ltd 18.11.2002; Elsevier
• Subjects: Anti-Bacterial Agents - chemical synthesis; Anti-Bacterial Agents - pharmacology; Anti-Bacterial Agents - toxicity; Antibacterial agents; Antibiotics. Antiinfectious agents. Antiparasitic agents; Benzoxazoles - chemical synthesis; Benzoxazoles - pharmacology; Benzoxazoles - toxicity; Biological and medical sciences; HeLa Cells; Humans; Medical sciences; Microbial Sensitivity Tests; Mycobacterium avium - drug effects; Mycobacterium kansasii - drug effects; Mycobacterium tuberculosis - drug effects; Pharmacology. Drug treatments; Structure-Activity Relationship; Nitro compound; Sulfur nitrogen heterocycle; Benzene derivatives; Mycobacterium kansasii; Mycobacterium avium; In vitro; Position isomer; Mycobacterium tuberculosis; Structure activity relation; Thioamide; Mycobacteriales; Mycobacteriaceae; Bicyclic compound; Bacteria; Actinomycetes; Antituberculous agent; Aromatic compound; Antibacterial agent; Chemical synthesis; Oxygen nitrogen heterocycle
• ISSN: 0960-894X; 1464-3405
• DOI: 10.1016/S0960-894X(02)00697-2

The series of 2-benzylsulfanyl derivatives of benzoxazole and benzothiazole were synthesized, evaluated for their in vitro antimycobacterial activity against Mycobacterium tuberculosis and non-tuberculous mycobacteria, and the activity expressed as the minimum inhibitory concentration (MIC) in μmol/L. The substances bearing two nitro groups ( 4e, 4f, 5e, 5f) or a thioamide group ( 4i, 4j, 5i, 5j) exhibited appreciable activity particularly against non-tuberculous strains. The most active compounds were subjected to the toxicity assay and were evaluated as moderately cytotoxic. The synthesis and biological activities of benzazole derivatives are reported. The most active compounds are those that contain nitro/thioamide groups.