ISSN print edition: 0366-6352
ISSN electronic edition: 1336-9075
Registr. No.: MK SR 9/7
Antimycobacterial 3-phenyl-4-thioxo-2H-1,3-benzoxazine-2(3H)-ones and 3-phenyl-2H-1,3-benzoxazine-2,4(3H)-dithiones substituted on phenyl and benzoxazine moiety in position 6
Eva Petrlíková, Karel Waisser, Rafael Doležal, Pavel Holý, Jiří Gregor, Jiři Kuneš, and Jarmila Kaustová
Department of Inorganic and Organic Chemistry, Charles University in Prague, Faculty of Pharmacy in Hradec Králové, Heyrovského 1203, CZ-50003 Hradec Králové, Czech Republic
Abstract: A series of forty-five derivatives of 3-phenyl-4-thioxo-2H-1,3-benzoxazine-2(3H)-ones and forty-five derivatives of 3-phenyl-2H-1,3-benzoxazine-2,4(3H)-dithiones was synthesised. The compounds exhibited in-vitro activity against Mycobacterium tuberculosis, M. kansasii (two strains), and M. avium. The most active derivatives were more active than isonicotinhydrazide (INH). The quantitative relationships between the
structure and antimycobacterial activity were calculated. The activity against M. tuberculosis increased with the lipophilicity of the substituents.
Keywords: benzoxazine – thioxo group – tuberculostatics – QSAR – antimycobacterial activity
Full paper is available at www.springerlink.com.
Chemical Papers 65 (3) 352–366 (2011)
Thursday, October 21, 2021