Influence of the replacement of the oxo function with the thioxo group on the antimycobacterial activity of 3-aryl-6,8-dichloro-2H-1,3-benzoxazine-2,4(3H)-diones and 3-arylquinazoline-2,4(1H,3H)-diones.
Series of 3-phenyl-6,8-dichloro-2H-1,3-benzoxazine-2,4(3H)-dithiones, 3-arylquinazoline-2,4(1H,3H)-diones and 3-arylquinazoline-2,4(1H,3H)-dithiones were synthesized, and the antimycobacterial activities of the derivatives evaluated in vitro. The compounds were active against Mycobacterium tuberculosis and conditionally pathogenic mycobacteria (Mycobacterium kansasii and Mycobacterium avium). The replacement of oxygen by sulfur in 3-phenyl-6,8-dichloro-2H-1,3-benzoxazine-2.4(3H)-diones and 3-arylquinazoline-2,4(1H,3H)-diones gave rise to an increase of antimycobacterial activity. The most active compound was 3-(3-chlorophenyl)-6,8-dichloro-2H-1,3-benzoxazine-2,4(3H)-dithione.
Waisser
K
K
Department of Inorganic and Organic Chemistry, Faculty of Pharmacy, Charles University, Hradec Králové, Czech Republic. waisser@faf.cuni.cz
Gregor
J
J
Dostál
H
H
Kunes
J
J
Kubicová
L
L
Klimesová
V
V
Kaustová
J
J
D000995:Antitubercular Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D008826:Microbial Sensitivity Tests; D009161:Mycobacterium / Q000187:drug effects*; D010078:Oxazines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D011799:Quinazolines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D013329:Structure-Activity Relationship
D000995:Antitubercular Agents; D010078:Oxazines; D011799:Quinazolines