The Oriented Development of Antituberculotics (Part II): Halogenated 3-(4-Alkylphenyl)-1,3-benzoxazine-2,4-(3H)-diones

• Published in: Archiv der Pharmazie (Weinheim) Vol. 340; no. 5; pp. 264 - 267
• Main Authors: Waisser, Karel, Matyk, Josef, Divišová, Hana, Husáková, Petra, Kuneš, Jirí, Klimešová, Vera, Palát, Karel, Kaustová, Jarmila
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 01.05.2007; WILEY‐VCH Verlag; Wiley
• Subjects: Antimycobacterial activity; Antitubercular Agents - chemical synthesis; Antitubercular Agents - chemistry; Antitubercular Agents - pharmacology; Antituberculotic activity; Benzoxazine; Chemistry; Chemistry, Medicinal; Chemistry, Multidisciplinary; Dioxoles - isolation & purification; Dioxoles - pharmacology; Life Sciences & Biomedicine; Magnetic Resonance Spectroscopy; Microbial Sensitivity Tests; Mycobacterium; Mycobacterium - drug effects; Oxazines - chemical synthesis; Oxazines - chemistry; Oxazines - pharmacology; Pharmacology & Pharmacy; Phenols - isolation & purification; Phenols - pharmacology; Physical Sciences; Salicylanilides - chemical synthesis; Salicylanilides - chemistry; Salicylanilides - pharmacology; Science & Technology; Structure-Activity Relationship; Tuberculostatics; 1-ARYL-5-BENZYLSULFANYLTETRAZOLES; benzoxazine; antimycobacterial activity; tuloerculostatics; antituberculotic activity
• ISSN: 0365-6233; 1521-4184
• DOI: 10.1002/ardp.200600002

Based on our previous studies, 21 new halogenated 3‐(4‐alkylphenyl)‐1,3‐benzoxazine‐2,4‐(3H)‐diones were synthesized by the reaction of salicylanilides and methyl‐chloroformate. All compounds were screened in vitro against three different strains of mycobacterium, and Free‐Wilson method was used to establish structure‐activity relationships. 6‐Bromo‐3‐(4‐butylphenyl)‐1,3‐benzoxazine‐2,4‐(3H)‐dione 3b proved to be the most active compound of the series.