Diacylhydrazide Based Amide Linked Oxadiazole Derivatives as Molecules of Biological Interest: Synthesis and Characterization

Abstract

Keeping in view the biological significance of heterocyclic compounds, the research work presented in this thesis, highlights the synthesis of biologically interesting novel acylhydrazide-1 ,3,4-oxadiazole hybrid compounds. Owing to the immense applications in medicinal field of 1,3,4-oxadiazole and acylhydrazide, these two moieties have been hybridized in designing of target molecules of substituted N-[ 4-(2-benzoylhydrazinecarbonyl)phenyl]-2-[(5-phenyl 1,3,4-oxadiazol-2-yl)thio]acetamide (XI) by using amide linkage. N-[4-(2-benzoylhydrazinecarbonyl)phenyl]-2-[(5-phenyl-l,3,4-oxadiazol-2- yl)thio ] acetamide (XI) synthesis started from 4-(2-chloroacetamido )benzoic acid (III). Substituted 1,3,4-oxadiazole thiol (VII) were prepared from differently substituted benzoic acid (IV) by various sequence of conversions. These substituted 1,3,4- oxadiazole thiols were converted to 4-(2-((5-phenyl-1,3,4-oxadiazol-2- yl)thio)acetamido)benzoic acid (X) by reaction with 4-(2-chloroacetamido)benzoic acid (III). Alkoxylbenzoylhydrazies (IX) were treated with 4-(2-((5-phenyl-1,3,4-oxadiazol-2- yl)thio )acetamido )benzoic acid (X) to afford substituted N-[ 4-(2- benzoylhydrazinecarbonyl)phenyl]-2-[(5-phenyl-1 ,3,4-oxadiazol-2-yl)thio ] acetamide (XI). The structure characterization of all the synthesized compounds was carried out using IR, IH and 13C-NMR spectroscopy.