Microwave assisted synthesis of some hybrid molecules derived from norfloxacin and investigation of their biological activities

Mentese M. Y., BAYRAK H., Uygun Y., Mermer A., Ülker S., Karaoglu S. A., ...More

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, vol.67, pp.230-242, 2013 (SCI-Expanded) identifier identifier identifier

  • Publication Type: Article / Article
  • Volume: 67
  • Publication Date: 2013
  • Doi Number: 10.1016/j.ejmech.2013.06.045
  • Journal Name: EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.230-242
  • Keywords: Norfloxacin, 1,3-Thiazole, 1,2,4-Triazole, Antimicrobial activity, Antiurease activity, ANTIBACTERIAL ACTIVITY, AMPHOTERICIN-B, QUINOLONE ANTIBACTERIALS, THIOUREA DERIVATIVES, DNA GYRASE, DRUG, INHIBITION, MECHANISM, BINDING, DESIGN
  • Karadeniz Technical University Affiliated: Yes

Abstract

Norfloxacin was converted to 7-(4-amino-2-fluorophenyl)piperazin derivative (2) via the formation of nitro compound. The synthesis of the norfloxacin derivatives containing 1,3-thiazole or 1,3-thiazolidin moiety was performed from the reaction of 4-chlorophenacylbromide or ethyl bromoacetate with compounds 4-7 obtained starting from 2. 3-Fluoro-4-[4-(2-methoxyphenyl)piperazin-1-yl]aniline (14), 5-{[4-(2-methoxyphenyl)piperazin-1-yl]methyl}-4-phenyl-4H-1,2,4-triazole-3-thiol (18) and {[4-(2-methoxy phenyl)piperazin-1-yl]methyl)-1,3,4-oxadiazol-2-thiol (19) were obtained starting from 1-(2-methoxyphenyl)piperazine by several steps. The treatment of hydrazide (16) with several aldehydes afforded N'-[(2-hydroxyphenyl)methylen]- (20), N'-[(3-hydroxy-4-methoxy phenyl)methylen]- (21) or N'-[1H-indol-3-ylmethylene]-2-[4-(2-methoxyphenyl)piperazin-1-yl]acetohydrazide (22). Then, compounds 14, 18, 19 and 22 were condensed with 7[4-(chloroacetyl)piperazin-1-yl]-1-ethyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (3) that was obtained from norfloxacine.