Synthesis and tuberculostatic activity of fluorine-containing derivatives of quinolone, quinazolinone, and benzothiazinone
Methods for the synthesis of fluorine-containing derivatives of quinolones, quinazolinones, and benzothiazinones based on the interaction of polyfluorobenzoic acid chloranhydrides with N,N-N,C-, and N,S-dinucleophiles are described. Use of (tetrafluorobenzoyl)isothiocyanate as the fluorine-containing block provides extensive opportunities for the synthesis of 2-substituted benzothiazinones. Some of the fluorine-containing azaheterocyclic compounds synthesized here had moderate and high activity against Mycobacterium tuberculosis H37Rv.
KeywordsAtomic Formula Quinazolinones Fluorobenzoyl Tuberculostatic Activity Tetrafluorobenzoyl
Unable to display preview. Download preview PDF.
- 1.D. Bouzard, “Recent developments in the chemistry of quinolones,” in: Antibiotic and Antiviral Compounds. Chemical Synthesis and Modification, R. Krohn, H. A. Kirst, H. Meeg (Eds.), Wienhiem, VCH Publishers Inc., New York (1993), pp. 187–203.Google Scholar
- 2.R. G. Glushkov, I. B. Levshin, N. B. Marchenko, et al., Khim.-Farm. Zh., 18, No. 9, 1048–1065 (1984).Google Scholar
- 3.G. A. Mokrushina, V. N. Charushin, and O. N. Chupakhin, Zh. Vses. Khim. O-va imeni D. I. Mendeleeva, 36, No. 4, 447–455 (1991).Google Scholar
- 4.G. A. Mokrushina, V. N. Charushin, and O. N. Chupakhin, Khim.-Farm. Zh., 29, No. 9, 5–19 (1995).Google Scholar
- 6.G. N. Lipunova, Je. V. Nosova, M. A. Kravchenko, et al., Khim.-Farm. Zh., 38, No. 11, 15–18 (2004).Google Scholar
- 9.É. V. Nosova, G. N. Lipunova, A. A. Laeva, and V. N. Charushin, Izv. Akad. Nauk., Ser. Khim., No. 3, 720–724 (2005).Google Scholar
- 10.G. N. Lipunova, É. V. Nosova, A. A. Laeva, et al., Zh. Organ. Khim., 41, No. 7, 1092–110 (2005).Google Scholar
- 11.É. V. Nosova, G. N. Lipunova, M. I. Kodess, et al., Izv. Akad. Nauk., Ser. Khim., No. 10, 2216–2220 (2004).Google Scholar
- 12.É. V. Nosova, G. N. Lipunova, A. A. Laeva, and V. N. Charushin, Zh. Organ. Khim., 41, No. 11, 1705–1711 (2005).Google Scholar
- 13.G. N. Lipunova, É. V. Nosova, G. A. Mokrushina, et al., Zh. Organ. Khim., 39, No. 2, 270–278 (2003).Google Scholar