Synthesis and DPPH radical-scavenging effect of novel heterocyclic derivatives of 2-amino-4-(1-benzoylindol-3-yl)selenophene-3-carbonitrile

El-Sawy, Eslam R.; Abo-Salem, Heba M.; Ebaid, Manal Sh.; El-Gendy, Abd El-Nasser; Mandour, Adel H.

doi:10.4103/1687-4315.124007

Synthesis and DPPH radical-scavenging effect of novel heterocyclic derivatives of 2-amino-4-(1-benzoylindol-3-yl)selenophene-3-carbonitrile

Authors

Abstract

Background and objectives
Selenophene moiety is one of the heterocyclic compounds with a selenium atom that plays a vital role in biological fields such as antioxidant, antidepressant, anticonvulsant, antimicrobial, and anticancer activities. The aim of this study was to describe the synthesis of some new heterocycles derived from 2-amino-4-(1-benzoylindol-3-yl)selenophene-3-carbonitrile derivatives and to evaluate their 2,2¢-diphenyl-1-picrylhydrazyl radical-scavenging activity.
Materials and methods
2-Amino-4-(1-benzoylindol-3-yl)selenophene-3-carbonitrile () was prepared and allowed to react with each of formic acid, formamide, carbon disulfide, urea, thiourea, malononitrile, or ethyl cyanoacetate to yield selenolo[2,3-]pyrimidines and selenolo[2,3-]pyridine derivatives and , respectively. Moreover, reaction of compound with hydrochloric acid or acetic anhydride in glacial acetic acid yielded selenolo[2,3-]pyrimidin-4-one and selenoacetamide derivative , respectively. In contrast, reaction of Schiff base with thioglycolic acid, phenacyl bromide, or chloroacetyl chloride yielded thiazolidine and azidatine derivatives and , respectively. Reaction of compound with some substituted benzenesulfonyl chlorides yielded sulfonamide derivatives , , , respectively. Moreover, 2-amino-1,3,4-thiadiazole and 4-oxo-2-iminothiazolidine derivatives were prepared through cyclization of hydrazinecarbothioamide or chloroacetamido derivative , respectively. The fusion of with succinic anhydride yielded pyrrolidine-2,5-dione , whereas heating of with succinic anhydride in ethanol yielded succinamic acid derivative . The newly synthesized compounds were screened for their 2,2′-diphenyl-1-picrylhydrazyl radical-scavenging activity.
Results and conclusion
Compound showed promising activity with a radical-scavenging effect (IC50) of 166.40 μg/ml compared with ascorbic acid (an IC50 of 129.64 μg/ml) as a reference standard.

Keywords