Microwave-assisted synthesis of some hybrid molecules containing penicillanic acid or cephalosporanic acid moieties and investigation of their biological activities.
Ethyl 4-amino-2-fluorophenylpiperazin-1-carboxylates containing a 1,3-oxazol(idin)e, 5-thioxo-1,2,4-triazole, 1,3,4-thiadiazole, 5-thioxo-1,3,4-oxadiazole, or 1,3-thiazole nucleus were obtained starting from ethyl piperazine-1-carboxylate (1) by several steps. The treatment of amine,3or hydrazide,9with several aromatic aldehydes generated the corresponding arylmethyleneamino (3a-f) or arylidenehydrazino (12a-c) compounds. The Mannich reaction between the 1,2,4-triazole or 1,3,4-oxadiazole compounds and 7-aca produced cephalosporanic acid derivatives. Penicillanic acid derivatives were obtained when 6-apa was used in the Mannich reactions. The synthesized compounds were screened for their antimicrobial, antilipase, and antiurease activities. Some of them were found to possess good-moderate antimicrobial activity against the test microorganisms. Two compounds exhibited antiurease activity, and four of them displayed antilipase activity.
Department of Chemistry, Faculty of Sciences, Karadeniz Technical University, 61080 Trabzon, Turkey.
Serap
S
Basoglu
Department of Biology, Recep Tayyip Erdogan University, 53100 Rize, Turkey.
Serdar
S
Ulker
Department of Biology, Recep Tayyip Erdogan University, 53100 Rize, Turkey.
Sengul
S
Alpay-Karaoglu
Department of Chemistry, Faculty of Sciences, Karadeniz Technical University, 61080 Trabzon, Turkey.
Neslihan
N
Demirbas
1,2,4-Triazole; 1,3-Oxa(thia)zole; 5-Oxo-1,3-oxazolidine; 6-Aminopenicillanic acid; 7-Aminocephalosporanic acid; Biological activity; Piperazine