A synthesis and study of the spatial structure of 3-acetyl-4-hydroxy-2-oxo-1,2-dihydroquinoline have been carried. 1-R-4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxylic acids [1-(4-hydroxy-2-oxo-1,2-dihydroquinolin-3-yl)ethylidene]hydrazides were prepared from this compound by two routes. A comparative analysis of the antitubercular properties of the synthesized compounds and of the closely structurally related N,N′-di(1-R-4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carbonyl)hydrazines has been performed.
Similar content being viewed by others
References
I. V. Ukrainets, A. A. Tkach, V. V. Kravtsova, and A. V. Turov, Khim. Geterotsikl. Soedin., 59 (2009). [Chem. Heterocycl. Comp., 45, 48 (2009)].
I. V. Ukrainets, Jaradat Nidal Amin, P. A. Bezuglyi, O. V. Gorokhova, L. V. Sidorenko, and I. V. Porokhnyak, Physiologically Active Substances [in Russian], No. 1 (27), 21 (1999).
Enomoto Hiroshi, Nomura Tadatoshi, Aoyagi Yoshiaki, Chokai Shoichi, Kono Tatsuhiko, Murase Masao, Inoue Kichiro, and Adachi Masahiro, US Pat. 4526894 (1985). http://ep.espacenet.com
T. Kappe, R. Aigner, P. Hohengassner, and W. Stadlbauer, J. Prakt. Chem., 336, 596 (1994).
C. M. Sarangi and Y. R. Rao, Res. Ind., 37, 113 (1992).
L. N. Nikolenko, Laboratory Handbook for Intermediate Products and Dyes [in Russian]), Vysshaya Shkola, Moscow (1961), p. 115.
H.-B. Burgi and J. D. Dunitz, Structure Correlation, Vol. 2, VCH, Weinheim (1994), p. 741.
Yu. V. Zefirov, Kristallografiya, 42, 936 (1997).
I. V. Ukrainets, A. A. Tkach, E. V. Mospanova, and E. N. Svechnikova, Khim. Geterotsikl. Soedin., 1196 (2007). [Chem. Heterocycl. Comp., 43, 1014 (2007)].
B. V. Ioffe, M. A. Kuznetsov, and A. A. Potekhin, Chemistry of Organic Hydrazide Derivatives [in Russian], Khimiya, Leningrad (1979), p. 55.
I. G. Zenkevich and B. V. Ioffe, Interpretation of the Mass Spectra of Organic Compounds [in Russian], Khimiya, Leningrad (1986), p. 104.
L. B. Heifets, in: L. B Heifets (editor), Drug Susceptibility in the Chemotherapy of Mycobacterial Infections, CRC Press, Boca Raton (1991), p. 89.
C. B. Inderleid and K. A. Nash, in: V. Lorian (editor), Antibiotics in Laboratory Medicine, Williams and Wilkins, Baltimore (1996), p. 127.
I. V. Ukrainets, A. A. Tkach, and Liu Yang Yang, Khim. Geterotsikl. Soedin., 1655 (2008). [Chem. Heterocycl. Comp., 44, 1347 (2008)].
I. V. Ukrainets, O. V. Gorokhova, S. G. Taran, P. A. Bezuglyi, A. V. Turov, N. A. Marusenko, and O. A. Evtifeeva, Khim. Geterotsikl. Soedin., 958 (1994). [Chem. Heterocycl. Comp., 30, 829 (1994)].
I. V. Ukrainets, P. A. Bezuglyi, V. I. Treskach, M. Yu. Kornilov, A. V. Turov, A. I. Maslennikov, S. V. Gladchenko, and V. I. Krivobok, Khim. Geterotsikl. Soedin., 1086 (1992). [Chem. Heterocycl. Comp., 28, 912 (1992)].
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).
Author information
Authors and Affiliations
Corresponding author
Additional information
*For Communication 151 see [1].
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 214–222, February, 2009.
Rights and permissions
About this article
Cite this article
Ukrainets, I.V., Tkach, A.A. & Yang, L.Y. 4-Hydroxy-2-quinolones. 152*. 3-acetyl-4-hydroxy-2-oxo-1,2-dihydroquinoline and its biologically active derivatives. Chem Heterocycl Comp 45, 169–175 (2009). https://doi.org/10.1007/s10593-009-0246-2
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10593-009-0246-2