Abstract
The reaction of 6-fluoro-2-methyl-1,2,3,4-tetrahydroquinoline with triethylmethanetricarboxylate gives di(9-fluoro-1-hydroxy-5-methyl-3-oxo-6,7-dihydro-3H,5H-pyrido[3,2,1-ij]quinolin-2-yl)methane and ethyl 9-fluoro-1-hydroxy-5-methyl-3-oxo-6,7-dihydro-3H,5H-pyrido[3,2,1-ij]quinoline-2-carboxylate from which alkyl-, dialkylaminoalkyl-, and hetarylamides as well as hydrazides were prepared. The structure and antitubercular properties of the compounds synthesized are discussed.
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I. V. Ukrainets, O. V. Gorokhova, L. V. Sidorenko, and N. L. Bereznyakova, Khim. Geterotsikl. Soedin., 1191 (2006). [Chem, Heterocycl. Comp., 42, 1032 (2006)].
A. Kleemann and J. Engel, Pharmaceutical Substances: Syntheses, Patents, Applications, Thieme Medical Publishers, Stuttgart (2001).
G. A. Mokrushina, V. N. Charushin, and O. N. Chupakhin, Khim.-Farm. Zh., 29, No. 9, 5 (1995).
J. S. Chapman, A. Bertasso, L. M. Cummings, and N. H. Georgopapadakou, Antimicrob. Agents Chemother., 39, 564 (1995).
M. P. Wentland, R. B. Perni, P. H. Dorff, R. P. Brundage, M. J. Castaldi, J. A. Carlson, T. R. Bailey, S. C. Aldous, P. M. Carabateas, E. R. Bacon, R. K. Kullnig, D. C. Young, M. G. Woods, S. D. Kingsley, K. A. Ryan, D. Rosi, M. L. Drozd, and F. J. Dutko, Drug. Des. Discov., 15, 25 (1997).
S. C. Beasley, N. Cooper, L. Gowers, J. P. Gregory, A. F. Haughan, P. G. Hellewell, D. Macari, J. Miotla, J. G. Montana, T. Morgan, R. Naylor, K. A. Runcie, B. Tuladhar, and J. B. Warneck, Bioorg. Med. Chem. Lett., 8, 2629 (1998).
L. L. Klein, D. T. Chu, L. L. Shen, and J. J. Plattner, European Patent 0424802 1991; http://ep.espacenet.com.
I. V. Ukrainets, L. V. Sidorenko, O. V. Gorokhova, and O. V. Shishkin, Khim. Geterotsikl. Soedin., 718 (2006). [Chem. Heterocycl. Comp., 42, 631 (2006)].
H.-B. Burgi and J. D. Dunitz, Struct. Correl., Vol. 2, VCH, Weinheim (1994), p. 741.
S. Jönsson, G. Andersson, T. Fex, T. Fristedt, G. Hedlund, K. Jansson, L. Abramo, I. Fritzson, O. Pekarski, A. Runström, H. Sandin, I. Thuvesson, and A. Björk, J. Med. Chem., 47, 2075 (2004).
I. V. Ukrainets, O. V. Gorokhova, L. V. Sidorenko, V. B. Rybakov, and V. V. Chernyshev, Zh. Org. Farm. Khim., 1, issue 3–4, 45 (2003).
A. Kutyrev and T. Kappe, J. Heterocycl. Chem., 34, 969 (1997).
A. Kutyrev and T. Kappe, J. Heterocycl. Chem., 36, 237 (1999).
I. V. Ukrainets, E. A. Taran, O. V. Shishkin, O. V. Gorokhova, S. G. Taran, N. A. Dzharadat, and A. V. Turov, Khim. Geterotsikl. Soedin., 516 (2000). [Chem. Heterocycl. Comp., 36, 443 (2000)].
S. H. Siddiqui in H. D. Isenberg (editor), Clinical Microbiology Procedures Handbook, Vol. 1, American Society for Microbiology, Washington DC (1992), p. 5.14.2
N. V. Likhanova, Dissertations of Candidates in Pharmaceutical Sciences, Kharkov (2000).
M. Amer, Dissertations of Candidates in Pharmaceutical Sciences, Kharkov (2002).
A. Dakkakh, Dissertations of Candidates in Pharmaceutical Sciences, Kharkov (2002).
G. M. Sheldrick, SHELX97. PC Version. A System of Computer Programs for Crystal Structure Solution and Refinement, Revision 2 (1998).
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1391–1407, September, 2006.
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Ukrainets, I.V., Sidorenko, L.V., Gorokhova, O.V. et al. 4-Hydroxy-2-quinolones. 108. N-R-amides of 9-fluoro-1-hydroxy-5-methyl-3-oxo-6,7-dihydro-3H,5H-pyrido[3,2,1-ij]quinoline-2-carboxylic acid and their antitubercular activity. Chem Heterocycl Compd 42, 1208–1222 (2006). https://doi.org/10.1007/s10593-006-0228-6
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DOI: https://doi.org/10.1007/s10593-006-0228-6