Highly Active Potential Antituberculotics: 3‐(4‐Alkylphenyl)‐4‐thioxo‐2H‐1,3‐benzoxazine‐2(3H)‐ones and 3‐(4‐Alkylphenyl)‐2H‐1,3‐benzoxazine‐2,4(3H)‐dihiones Substituted in Ring‐B by Halogen

A series of 6‐chloro‐3‐(4‐alkylphenyl)‐4‐thioxo‐2H‐1,3‐benzoxazine‐2(3H)‐ones, 7‐chloro‐3‐(4‐alkylphenyl)‐4‐thioxo‐2H‐1,3‐benzoxazine‐2(3H)‐ones, 6‐bromo‐3‐(4‐alkylphenyl)‐4‐thioxo‐2H‐1,3‐benzoxazine‐2(3H)‐ones, 6,8‐dibromo‐3‐(4‐alkylphenyl)‐4‐thioxo‐2H‐1,3‐benzoxazine‐2(3H)‐ones, 6‐chloro‐3‐(4‐alky...

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Bibliographic Details
Published in:Archiv der Pharmazie (Weinheim) 2008-12, Vol.341 (12), p.800-803
Main Authors: Waisser, Karel, Matyk, Josef, Kuneš, Jirí, Doležal, Rafael, Kaustová, Jarmila, Dahse, Hans‐Martin
Format: Article
Language:English
Subjects:
Antimycobacteroal activity
Antitubercular Agents - chemical synthesis
Antitubercular Agents - pharmacology
Antituberculotics
Benzoxazine
Benzoxazines - chemical synthesis
Benzoxazines - pharmacology
Microbial Sensitivity Tests
Mycobacterium avium
Mycobacterium tuberculosis
Mycobacterium tuberculosis - drug effects
Structure-Activity Relationship
Thioxo group
Tuberculostatics
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Summary:A series of 6‐chloro‐3‐(4‐alkylphenyl)‐4‐thioxo‐2H‐1,3‐benzoxazine‐2(3H)‐ones, 7‐chloro‐3‐(4‐alkylphenyl)‐4‐thioxo‐2H‐1,3‐benzoxazine‐2(3H)‐ones, 6‐bromo‐3‐(4‐alkylphenyl)‐4‐thioxo‐2H‐1,3‐benzoxazine‐2(3H)‐ones, 6,8‐dibromo‐3‐(4‐alkylphenyl)‐4‐thioxo‐2H‐1,3‐benzoxazine‐2(3H)‐ones, 6‐chloro‐3‐(4‐alkylphenyl)‐2H‐1,3‐benzoxazine‐2,4(3H)‐dithiones, 7‐chloro‐3‐(4‐alkylphenyl)‐2H‐1,3‐benzoxazine‐2,4(3H)‐dithiones, 6‐bromo‐3‐(4‐alkylphenyl)‐2H‐1,3‐benzoxazine‐2,4(3H)‐dithiones and 6,8‐dibromo‐3‐(4‐alkylphenyl)‐2H‐1,3‐benzoxazine‐2,4(3H)‐dithiones was synthesized. The compounds exhibited in‐vitro activity against Mycobacterium tuberculosis, M. kansasii (two strains), and M. avium. 6‐bromo‐3‐(4‐propylphenyl)‐4‐thioxo‐2H‐1,3‐benzoxazin‐2(3H)‐one and 6‐bromo‐3‐(4‐propylphenyl)‐2H‐1,3‐benzoxazin‐2,4(3H)‐dithione are the most active compounds against M. tuberculosis. The activity is similar to isoniazid (INH). The compounds under study have a broad spectrum of activity against potential pathogenic strains. The replacement of the oxo group by thioxo group of 3‐(4‐alkylphenyl)‐2H‐1,3‐benzoxazine‐2,4(3H)‐diones often led to an improvement in the antimycobacterial activity against M. tuberculosis.
ISSN:0365-6233
1521-4184
DOI:10.1002/ardp.200800004