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

• Published in: Chemistry of heterocyclic compounds (New York, N.Y. 1965) Vol. 45; no. 9; pp. 1058 - 1068
• Main Authors: Ukrainets, I. V, Grinevich, L. A, Tkach, A. A, Bevz, O. V, Slobodzian, S. V
• Format: Journal Article
• Language: English
• Published: Boston Boston : Springer US 01.09.2009; Springer US; Springer Nature
• Subjects: 1-R-4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxamides; 2-aminopyrazine; antitubercular activity; bromination; Chemistry; Chemistry and Materials Science; Chemistry, Organic; Organic Chemistry; Pharmacy; Physical Sciences; Science & Technology; X-ray structural analysis; X-ray structural analysis; antitubercular activity; 1-R-4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxamides; 2-aminopyrazine; bromination; VITRO; ANTIMYCOBACTERIAL; T-705; IN-VIVO ACTIVITIES; DERIVATIVES; PYRAZINE
• ISSN: 0009-3122; 1573-8353
• DOI: 10.1007/s10593-009-0384-6

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.