Imine/amide-imidazole conjugates derived from 5-amino-4-cyano-N1-substituted benzyl imidazole: Microwave-assisted synthesis and anticancer activity via selective topoisomerase-II-α inhibition

Bioorg Med Chem. 2015 Sep 1;23(17):5654-61. doi: 10.1016/j.bmc.2015.07.020.

Arvind Negi ¹, Jimi Marin Alex ¹, Suyog M Amrutkar ², Ashish T Baviskar ², Gaurav Joshi ¹, Sandeep Singh ³, Uttam C Banerjee ², Raj Kumar ⁴

Affiliations

1 Laboratory for Drug Design and Synthesis, Centre for Chemical and Pharmaceutical Sciences, Central University of Punjab, 151 001 Bathinda, India.
2 Department of Pharmaceutical Technology (Biotechnology), National Institute of Pharmaceutical Education and Research (NIPER), Mohali, S.A.S. Nagar, Sec 67, 160 062 Punjab, India.
3 Centre for Genetic Diseases and Molecular Medicine, Central University of Punjab, 151 001 Bathinda, India.
4 Laboratory for Drug Design and Synthesis, Centre for Chemical and Pharmaceutical Sciences, Central University of Punjab, 151 001 Bathinda, India. Electronic address: raj.khunger@gmail.com.

PMID: 26216018 DOI: 10.1016/j.bmc.2015.07.020

Abstract

Microwave-accelerated synthesis and Anticancer activity of novel imine/amide-imidazole conjugates derived from 5-amino-4-cyano-N1-substituted benzyl imidazole against a panel of seven Cancer cell lines are reported for the first time. Compounds ARK-4, 10 and 12 in the series show promising in vitro anti proliferative activity with low micromolar IC50 values against A-459 (lung), Hep-G2 (liver) and H-460 (liver) Cancer cell lines. Compounds caused the increase in ROS levels as well as mitochondrial membrane depolarization, which might induce Apoptosis. Further, mechanistic interventions on biological and molecular modeling data supported that compounds inhibited topoisomerase-II selectively.

Keywords

Anticancer activity; Antioxidant activity; Imine/amide–imidazole; Molecular modeling; Topoisomerase inhibition.

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