ISSN print edition: 0366-6352 ISSN electronic edition: 1336-9075 Registr. No.: MK SR 9/7 Published monthly

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

E-mail: eva.petrlikova@faf.cuni.cz

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.

DOI: 10.2478/s11696-011-0020-7

Chemical Papers 65 (3) 352–366 (2011)