Benzo[d]imidazol-5-yl)-5-(substituted)-1,3,4-Oxadiazoles: Synthesis, Anticancer, Antimicrobial and In Silico Studies

Author(s): Naveen Kumar, Swamy Sreenivasa*, Bhuvanesh Sukhlal Kalal, Vasantha Kumar, Bantwal Shivarama Holla, Vinitha Ramanath Pai, Nadigar Revansiddappa Mohan, Shivaraj Govindaiah.

Journal Name: Letters in Drug Design & Discovery

Volume 16 , Issue 9 , 2019

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Graphical Abstract:


Background: Cancer is a fatal disease for mankind; continuous research is still going on for the invention of potent anticancer drugs. In this view, 1, 3, 4-Oxadiazoles are privileged molecules which attracted medicinal chemists towards their anticancer properties.

Methods: A new series of benzo[d]imidazol-5-yl)-5-(substituted)-1,3,4-oxadiazole derivatives was synthesized in an efficient ‘one-pot’ nitro reductive cyclization using sodium dithionite as a cyclizing agent by a conventional method with good yield. All the structures of the synthesized molecules were characterized by IR, 1H NMR, HRMS and Mass spectral analysis. Anticancer activity screening against A375 melanoma cancer cell line and MDA-MB-231 breast cancer cell line along with antimicrobial activity were carried out using agar well diffusion method.

Results: Compounds 8a and 8j of the series emerged as potent anticancer agents against A375 melanoma cancer cell line with IC50 47.06 µM and 36.76 µM, respectively. In silico studies also revealed that compounds 8a and 8j showed highest interaction with 2OH4 protein of VEGFR-2 tyrosine kinase. Substantial antibacterial and antifungal activities against the tested microorganism were observed for compounds 8j and 8g.

Conclusion: Potent anticancer property has been observed with 1,3,4-Oxadiazole linked tetrafluro substituted benzene ring 8j indicating that future research on these type of molecules can be continued to improve the anticancer activity.

Keywords: Benzimidazole, oxadiazole, antimicrobial, anticancer, docking, 2OH4 protein, VEGFR-2 tyrosine kinase.

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Year: 2019
Page: [994 - 1005]
Pages: 12
DOI: 10.2174/1570180816666181220123924

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