Synthesis of Some 2,3-Dihydro-1,3,4-Oxadiazoles and 4,5-Dihydro-1,2,4-Triazoles as Anticancer Agents

Abstract

Objective: The main objective of this work was to synthesize and evaluate the novel 2,3-dihydro-1,3,4-oxadiazole and 4,5-dihydro-1,2,4-triazole derivatives for cytotoxic activities.
 Methods: The 2,3-dihydro-1,3,4-oxadiazole derivatives 4a-h were synthesized by cyclization of N'-(substituted-benzylidene) isonicotinohydrazide 3a-e in refluxing acetic anhydride. The 2,3-dihydro-1,3,4-oxadiazole derivatives 4a-h were converted into the corresponding 4,5-dihydro-1,2,4-triazoles 5a-h using ammonia. All the synthesized compounds were identified, depending on the physical and spectral data. Title compounds were assessed for their cytotoxic activity against human cancer cell line (MCF-7) by using Sulforhodamine B (SRB) colorimetric assay.
 Results: All the synthesized compounds showed characteristic peaks in FTIR, 1HNMR and Mass spectral analysis. The results of the in vitro cytotoxic activity revealed that the compound 4c exhibited equipotent cytotoxic activity with an IC50 value of 8.04 µM when compared with that of standard drug doxorubicin (IC50= 8.02 µM). The reminder compounds have shown good to moderate cytotoxic activities when compared with that of a reference standard.
 Conclusion: We synthesized a series of title compounds in quantitative yields. Most derivatives showed moderate to good cytotoxic activity.

In Silico Evaluation of Binding Interaction and Adme Properties of Novel 5-(Thiophen-2-Yl)-1,3,4-Oxadiazole-2-Amine Derivatives as Anti-Proliferative Agents

“…The 1,3,4-oxadiazole ring can function as bio-isostere for compounds that have carbonyl, ester, amide, and carbamate groups and it can be used as a major part of the leading pharmacophore which can interact with the ligand. Additionally, as a flat aromatic moiety, it provides the proper positioning of the molecule [8], and derivatives with the 1,3,4oxadiazole nucleus exhibit ability of different biological actions such as anti-cancer [9,10], antioxidant [11], and antibacterial [12].…”