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, cilt.69, ss.622-631, 2013 (SCI İndekslerine Giren Dergi) identifier identifier identifier

  • Cilt numarası: 69
  • Basım Tarihi: 2013
  • Doi Numarası: 10.1016/j.ejmech.2013.07.040
  • Dergi Adı: EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
  • Sayfa Sayıları: ss.622-631

Özet

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).

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).

The synthesized compounds were screened for their antimicrobial and antiurease activities. Some of them were found to possess good moderate antimicrobial activity against the test microorganisms. Compound 5d was observed to have moderate anti-urease activity.