Design, synthesis and biological activities of some 7-aminocephalosporanic acid derivatives

Basoglu S., DEMİRBAŞ A., Ulker S., Alpay-Karaoglu S., DEMİRBAŞ N.

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, vol.69, pp.622-631, 2013 (SCI-Expanded) identifier identifier identifier

  • Publication Type: Article / Article
  • Volume: 69
  • Publication Date: 2013
  • Doi Number: 10.1016/j.ejmech.2013.07.040
  • Journal Name: EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.622-631
  • Keywords: 7-Aminocephalosporanic acid, 1,3-Oxazole, 1,3-Thiazole, Antimicrobial activity, Anti-urease activity, Anti beta-lactamase activity, BETA-LACTAMASE, ANTIMICROBIAL ACTIVITY, HYBRID MOLECULES, AKT INHIBITORS, RESISTANT, CEPHALOSPORINS, 4-THIAZOLIDINONES, ANTIBACTERIAL, COMBINATION, ANTIFUNGAL
  • Recep Tayyip Erdoğan University Affiliated: Yes

Abstract

The treatment of 7-ACA with 4-substituted benzensulfonyl chlorides afforded the compounds containing 4-nitro/aminophenyl sulfonylamino moiety in the cephalosporanic acid skeleton (2, 4). The synthesis of the cephalosporanic acid derivatives containing 1,3-thiazole or 5-oxo-1,3-thiazolidine nucleus and sulfonamide function (8a, 8b, 10) was performed starting from 7-ACA by several steps. The reaction of 7ACA with [4-(2-fluoro-4-nitrophenyl)piperazin-1-yl]acetyl chloride afforded the corresponding 7{[4-(2-fluoro-4-nitrophenyl)piperazin-1-yl]acetyl)amino derivative (13).