Synthesis and Pharmacological Activity of Ethyl-2-Amino-1-Benzamido-4-Oxo-5-(2-Oxo-2-Arylethylidene)Pyrrolidine-3-Carboxylates

Abstract

Ethyl-2-amino-1-benzamido-4-oxo-5-(2-oxo-2-arylethylidene)pyrrolidine-3-carboxylates (IIa-g) were synthesized via recyclization of 3-(2-benzoylhydrazono)-5-arylfuran-2(3H)-ones (I) through the action of ethylcyanoacetate. The synthesized compounds were screened for biological activity and were found to have low toxicity. Ethyl-2-amino-1-benzamido-5-[2-(3, 4-dimethoxyphenyl)-2-oxoethylidene]-4-oxopyrrolidine-3-carboxylate exhibited antiradical activity in a diphenylpicrylhydrazyl (DPPH)-binding assay that was greater than that of the reference drug trolox. This same compound showed anti-inflammatory activity in a carrageenan edema model that was greater than that of diclofenac sodium. Assessment of antihypoxic activity in an acute normobaric hypoxia test found that ethyl-2-amino-1-benzamido-5-[2-oxo-2-(4-methylphenyl) ethylidene]-4-oxopyrrolidine-3-carboxylate was comparable with the succinic acid standard.