Synthesis, antimicrobial activity and QSARs of new benzoxazine-3-ones

• Published in: European journal of medicinal chemistry 2006-12, Vol.41 (12), p.1398-1404
• Main Authors: Alper-Hayta, S., Akı-Sener, E., Tekiner-Gulbas, B., Yıldız, I., Temiz-Arpacı, O., Yalcın, I., Altanlar, N.
• Format: Article
• Language: English
• Subjects: 1,4-Benzoxazine-3-one; Anti-Bacterial Agents - chemical synthesis; Anti-Bacterial Agents - chemistry; Anti-Bacterial Agents - pharmacology; Antibacterial activity; Antibacterial agents; Antibiotics. Antiinfectious agents. Antiparasitic agents; Antifungal activity; Antifungal agents; Antifungal Agents - chemical synthesis; Antifungal Agents - chemistry; Antifungal Agents - pharmacology; Benzoxazines - chemical synthesis; Benzoxazines - chemistry; Benzoxazines - pharmacology; Biological and medical sciences; General aspects; Magnetic Resonance Spectroscopy; Medical sciences; Microbial Sensitivity Tests; Pharmacology. Drug treatments; QSAR; Quantitative Structure-Activity Relationship; Spectrophotometry, Infrared
• ISSN: 0223-5234; 1768-3254
• DOI: 10.1016/j.ejmech.2006.06.011

New ethyl 3,4-dihydro-3-oxo-4,6,7-trisubstituted-2 H-1,4-benzoxazine-2-acetate derivatives were synthesized and their structures were elucidated by IR, 1H NMR and mass spectral data. Antimicrobial activity of the compounds was investigated by using the method of twofold serial dilution technique against different Gram-positive, Gram-negative bacteria and some Candida species in comparison to standard drugs. Microbiological results indicated that the synthesized compounds possessed a broad spectrum of activity having MIC values of 6.25–100 μg/ml against the tested microorganisms. The QSAR analysis of a set of these compounds tested for growth inhibitory activity against Candida krusei was performed by using the computer-assisted multiple regression procedure. The activity contributions for substituent effects of these compounds were determined from the correlation equation for predictions of the lead optimization. [Display omitted] New ethyl 3,4-dihydro-3-oxo-4,6,7-trisubstituted-2 H-1,4-benzoxazine-2-acetate derivatives were synthesized and antimicrobial activity of the compounds was investigated. The QSAR analysis of a set of these compounds tested for growth inhibitory activity against Candida krusei was performed. The activity contributions for substituent effects of these compounds were determined from the correlation equation for prediction of the lead optimization.