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4-Hydroxy-2-quinolones 148. Synthesis and antitubercular activity of 1-hydroxy-3-oxo-6,7-dihydro-3H,5H-pyrido[3,2,1-ij]quinoline-2-carboxylic acid N-R-amides

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

An improved method for the preparation of ethyl 1-hydroxy-3-oxo-6,7-dihydro-3H,5H-pyrido[3,2,1-ij]quinoline-2-carboxylate has been proposed and a series of hetarylamides has been synthesized from it. A comparative analysis has been carried out of the antitubercular activities of the synthesized compounds with the active structural analogs 4-hydroxy-2-oxo-1,2-dihydroquinoline-3 and 1-hydroxy-3-oxo-5,6-dihydro-3H-pyrrolo[3,2,1-ij]quinoline-2-carboxamides studied before.

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References

  1. I. V. Ukrainets, N. L. Bereznyakova, and A. V. Turov, Khim. Geterotsikl. Soedin., 1039 (2008). [Chem. Heterocycl. Comp., 44, 833 (2008)].

    Google Scholar 

  2. N. Frimodt-Moller, A. M. Hammerum, L. Bagger-Skjot, J. H. Hessler, C. T. Brandt, R. L. Skov, and D. L. Monnet, Ugeskr. Laeger, 168, 3039 (2006).

    Google Scholar 

  3. R. Johnson, E. M. Streicher, G. E. Louw, R. M. Warren, P. D. van Helden, and T. C. Victor, Curr. Issues, Mol. Biol., 8, 97 (2006).

    CAS  Google Scholar 

  4. S. K. Sharma and A. Mohan, Chest, 130, 261 (2006).

    Article  CAS  Google Scholar 

  5. A. D. Harries and C. Dye, Ann. Trop. Med. Parasitol., 100, 415 (2006).

    Article  CAS  Google Scholar 

  6. A. I. de la Iglesia and H. R. Morbidoni, Rev. Argent. Microbiol., 38, 97 (2006).

    Google Scholar 

  7. A. J. Steyn, J. Chan, and V. Mehra, Curr. Opin. Infect. Dis., 12, 415 (1999).

    CAS  Google Scholar 

  8. I. V. Ukrainets, E. V. Mospanova, and L. V. Sidorenko, Khim. Geterotsikl. Soedin., 1023 (2007). [Chem. Heterocycl. Comp., 43, 863 (2007)].

    Google Scholar 

  9. I. V. Ukrainets, N. L. Bereznyakova, and E. V. Mospanova, Khim. Geterotsikl. Soedin., 1015 (2007). [Chem. Heterocycl. Comp., 43, 863 (2007)].

    Google Scholar 

  10. I. V. Ukrainets, L. V. Sidorenko, O. V. Gorokhova, E. V. Mospanova, and O. V. Shishkin, Khim. Geterotsikl. Soedin., 718 (2006). [Chem. Heterocycl. Comp., 43, 856 (2007)].

    Google Scholar 

  11. 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 

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

    Google Scholar 

  13. Yu. V. Zefirov, Kristallografiya, 42, 936 (1997).

    CAS  Google Scholar 

  14. N. S. Zefirov, V. A. Palyulin, and E. E. Dashevskaya, J. Phys. Org. Chem., 3, 147 (1990).

    Article  CAS  Google Scholar 

  15. L. B. Heifets, in: L. B. Heifets (editor), Drug Susceptibility in the Chemotherapy of Mycobacterial Infections, CRC Press, Boca Raton (1991), p. 89.

    Google Scholar 

  16. C. B. Inderleid and K. A. Nash in V. Lorian (editor), Antibiotics in Laboratory Medicine, Williams and Wilkins, Baltimore (1996), p. 127.

    Google Scholar 

  17. A. Kutyrev and T. Kappe, J. Heterocyclic Chem., 34, 969 (1997).

    Article  CAS  Google Scholar 

  18. G. M. Sheldrick, SHELXTL PLUS. PC Version. A System of Computer Programs for the Determination of Crystal Structure from X-ray Diffraction Data, Rev. 5.1 (1998).

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Authors and Affiliations

  1. National University of Pharmacy, Kharkiv, 61002, Ukraine

    I. V. Ukrainets, A. A. Tkach & L. A. Grinevich

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  1. I. V. Ukrainets
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  2. A. A. Tkach
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  3. L. A. Grinevich
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Correspondence to I. V. Ukrainets.

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__________

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1189–1202, August, 2008.

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Ukrainets, I.V., Tkach, A.A. & Grinevich, L.A. 4-Hydroxy-2-quinolones 148. Synthesis and antitubercular activity of 1-hydroxy-3-oxo-6,7-dihydro-3H,5H-pyrido[3,2,1-ij]quinoline-2-carboxylic acid N-R-amides. Chem Heterocycl Comp 44, 956–966 (2008). https://doi.org/10.1007/s10593-008-0139-9

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  • DOI: https://doi.org/10.1007/s10593-008-0139-9

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