4-HYDROXY-2-QUINOLONES.168. SYNTHESIS, CHEMICAL AND ANTITUBERCULAR PROPERTIES OF 1-R-4-HYDROXY-2-OXO-1,2-DIHYDROQUINOLINE-3-CARBOXYLIC ACID PYRAZIN-2-YLAMIDES

Authors

  • И. В. Украинец National University of Pharmacy, Kharkiv 61002
  • Л. А. Гриневич National University of Pharmacy, Kharkiv 61002
  • А. А. Ткач National University of Pharmacy, Kharkiv 61002
  • О. В. Бевз National University of Pharmacy, Kharkiv 61002
  • С. В. Слободзян Northern Michigan University, Marquette 49855, Michigan

DOI:

https://doi.org/10.1007/6582

Keywords:

2-aminopyrazine, 1-R-4-hydroxy-2-oxo-1, 2-dihydroquinoline-3-carboxamides, bromination, antitubercular activity, X-ray structural analysis

Abstract

1-R-4-Hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxylic acid pyrazin-2-ylamides have been synthesized as potential antitubercular agents. In contrast to pyrimidin-2-ylamides the compounds prepared are brominated by molecular bromine in glacial acetic acid at position 6 of the quinolone ring rather than in the amide part of the molecule. The 1-N-allyl derivative behaves similarly but undergoes halocyclization to give 2-bromomethyl-5-oxo-1,2-dihydro-5H-oxazolo[3,2-a]quinoline-4-carboxylic acid pyrazin-2-ylamide. A comparative analysis of  the antimycobacterial properties of the synthesized compounds and their isomeric pyrimidin-2-ylamides has been carried out.

How to Cite
Ukrainets, I. V.; Grinevich, L. A.; Tkach, A. A.; Bevz, O. V.;  Slobodzian, S. V.  Chem. Heterocycl. Compd. 2009, 45, 1058. [Khim. Geterotsikl. Soedin. 2009, 1324.]

For this article in the English edition see DOI 10.1007/s10593-009-0384-6

 

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Published

2022-02-14

Issue

No. 9 (2009)

Section

Original Papers