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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

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Chemistry of Heterocyclic Compounds Aims and scope

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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References

  1. I. V. Ukrainets, O. V. Gorokhova, L. V. Sidorenko, and N. L. Bereznyakova, Khim. Geterotsikl. Soedin., 1191 (2006). [Chem, Heterocycl. Comp., 42, 1032 (2006)].

    Google Scholar 

  2. A. Kleemann and J. Engel, Pharmaceutical Substances: Syntheses, Patents, Applications, Thieme Medical Publishers, Stuttgart (2001).

    Google Scholar 

  3. G. A. Mokrushina, V. N. Charushin, and O. N. Chupakhin, Khim.-Farm. Zh., 29, No. 9, 5 (1995).

    CAS  Google Scholar 

  4. J. S. Chapman, A. Bertasso, L. M. Cummings, and N. H. Georgopapadakou, Antimicrob. Agents Chemother., 39, 564 (1995).

    CAS  Google Scholar 

  5. 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).

    CAS  Google Scholar 

  6. 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).

    Article  CAS  Google Scholar 

  7. L. L. Klein, D. T. Chu, L. L. Shen, and J. J. Plattner, European Patent 0424802 1991; http://ep.espacenet.com.

  8. I. V. Ukrainets, L. V. Sidorenko, O. V. Gorokhova, and O. V. Shishkin, Khim. Geterotsikl. Soedin., 718 (2006). [Chem. Heterocycl. Comp., 42, 631 (2006)].

    Google Scholar 

  9. H.-B. Burgi and J. D. Dunitz, Struct. Correl., Vol. 2, VCH, Weinheim (1994), p. 741.

    Google Scholar 

  10. 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).

    Article  CAS  Google Scholar 

  11. 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).

    CAS  Google Scholar 

  12. A. Kutyrev and T. Kappe, J. Heterocycl. Chem., 34, 969 (1997).

    Article  CAS  Google Scholar 

  13. A. Kutyrev and T. Kappe, J. Heterocycl. Chem., 36, 237 (1999).

    CAS  Google Scholar 

  14. 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)].

    Google Scholar 

  15. 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

    Google Scholar 

  16. N. V. Likhanova, Dissertations of Candidates in Pharmaceutical Sciences, Kharkov (2000).

  17. M. Amer, Dissertations of Candidates in Pharmaceutical Sciences, Kharkov (2002).

  18. A. Dakkakh, Dissertations of Candidates in Pharmaceutical Sciences, Kharkov (2002).

  19. G. M. Sheldrick, SHELX97. PC Version. A System of Computer Programs for Crystal Structure Solution and Refinement, Revision 2 (1998).

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Authors and Affiliations

  1. National Pharmaceutical University, Kharkiv, 61002, Ukraine

    I. V. Ukrainets, L. V. Sidorenko & O. V. Gorokhova

  2. Institute of Scintillation Materials, Ukraine National Academy of Sciences, Kharkiv, 61001

    O. V. Shishkin

  3. Taras Shevchenko National University, Kiev, 01033, Ukraine

    A. V. Turov

Authors
  1. I. V. Ukrainets
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  2. L. V. Sidorenko
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  3. O. V. Gorokhova
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  4. O. V. Shishkin
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  5. A. V. Turov
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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

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