Antimycobacterial 3-aryl-2H-1,3-benzoxazine-2,4(3H)-diones.
A series of 153 derivatives of 3-phenyl-2H-benzoxazine-2,4(3H)-dione substituted in position 6 or 7 on benzoxazine and on the phenyl ring was synthesized. The compounds were evaluated in vitro for antimycobacterial activity against Mycobacterium tuberculosis, Mycobacterium kansasii and Mycobacterium avium. The activity of the compounds increases with increasing hydrophobicity and electron-withdrawing properties of the substituents on the phenyl ring, whereas the effect of the substituents on the benzoxazine ring seems to be more complex.
Waisser
K
K
Department of Inorganic and Organic Chemistry, Faculty of Pharmacy, Charles University, Hradec Králové, Czech Republic. waisser@faf.cuni.cz
Bures
O
O
Holý
P
P
Kunes
J
J
Oswald
R
R
Jirásková
L
L
Pour
M
M
Klimesová
V
V
Palát
K
K
Kaustová
J
J
Danse
H M
HM
Möllmann
U
U
D000465:Algorithms; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000494:pharmacology*; D055598:Chemical Phenomena; D002627:Chemistry, Physical; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D008826:Microbial Sensitivity Tests; D009161:Mycobacterium / Q000187:drug effects*; D010078:Oxazines / Q000138:chemical synthesis* / Q000494:pharmacology*; D013055:Spectrophotometry, Infrared; D013329:Structure-Activity Relationship
D000900:Anti-Bacterial Agents; D007202:Indicators and Reagents; D010078:Oxazines