Mn(II) assisted synthesis of N-phenyl-5-(pyridin-3-yl)-1,3,4-oxadiazol-2-amine and evaluation of its antiproliferative activity

The global burden of cervical cancer is continuously increasing day by day affecting the world population. Wide arrays of agents are prevalent for the treatment of this chronic disease but the survival rates are still limited. The titled compound N-phenyl-5-(pyridin-3-yl)-1,3,4-oxadiazol-2-amine (Pypao) was prepared through the cyclization of nicotinoyl-N-phenyl hydrazine carbothioamide catalyzed by manganese (II) acetate. Uv-Vis, IR, NMR, elemental analyses, and single-crystal X-ray data were utilized for the description of the compound Pypao. The crystal structure of Pypao is stabilized via intermolecular hydrogen bonding interactions, which is further confirmed with Hirshfeld surface analysis. The DFT methods were also used to optimize the Pypao and obtained bond parameters have been found coherent with the experimental data. FMO and TD-DFT studies are also performed to gain insights into the electronic behavior of Pypao. Furthermore, the binding potential of Pypao to different oncoproteins of HPV namely E6, E6AP, and E7 have been examined through a molecular docking study. The in-vitro anticancer activity of Pypao has been investigated against SiHa cells. The anticancer potential of Pypao has been evaluated through various assays including MTT, DAPI stating, AO/PI staining, etc. Both time and dose-dependent activity of Pypao have been investigated.