Highly active antimycobacterial derivatives of benzoxazine.
New 3-(4-alkylphenyl)-4-thioxo-2H-1,3-benzoxazine-2(3H)-ones and 3-(4-alkylphenyl)-2H-1,3-benzoxazine-2,4(3H)-dithiones were synthesized. The compounds were tested for in vitro antimycobacterial activity against Mycobacterium tuberculosis, Mycobacterium avium and two strains of Mycobacterium kansasii. The antimycobacterial activity increased with the replacement of the carbonyl group by the thiocarbonyl group in the starting 3-(4-alkylphenyl)-2H-1,3-benzoxazine-2,4(3H)-diones. The most active derivatives were more active than isonicotinhydrazide (INH). Free-Wilson analysis was also carried out and the activity contribution was examined.
Department of Inorganic and Organic Chemistry, Charles University in Prague, Hradec Králové, Czech Republic. Eva.Petrlikova@faf.cuni.cz
Eva
E
Petrlíková
Karel
K
Waisser
Hana
H
Divišová
Petra
P
Husáková
Petra
P
Vrabcová
Jiří
J
Kuneš
Karel
K
Kolář
Jiřina
J
Stolaříková
D000995:Antitubercular Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D048588:Benzoxazines / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D007538:Isoniazid / Q000494:pharmacology; D008826:Microbial Sensitivity Tests; D009162:Mycobacterium avium / Q000187:drug effects*; D019909:Mycobacterium kansasii / Q000187:drug effects*; D009169:Mycobacterium tuberculosis / Q000187:drug effects*; D013329:Structure-Activity Relationship
D000995:Antitubercular Agents; D048588:Benzoxazines; D007538:Isoniazid