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Issue 20, 2018
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Design and synthesis of novel oleanolic acid based chromenes as anti-proliferative and anti-inflammatory agents

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Abstract

A practical and novel approach has been developed for the synthesis of oleanolic acid based chromene analogues. Different α,β-unsaturated carbonyl and chromene derivatives of oleanolic acid were synthesized and evaluated for their anticancer activity. Compounds 6e, 6k, 7e and 7g showed significant anticancer activity within the IC50 range of 12.23–39.04 μg mL−1. The promising derivatives 7e and 7g were further analyzed for their effects on the cell cycle and apoptosis in A-549 and MDA-MB-231 cells, and it was depicted that 7e and 7g triggered apoptosis in A-549 and MDA-MB-231 cells and arrested the cell population in the G2/M phase. The anticancer activity of the most active analogue 7g occurred through microtubule destabilization (IC50: ∼3.6 μg mL−1), and it was found to be non-toxic against human erythrocytes. The compounds 7e and 7g significantly inhibited the proinflammatory cytokines TNF-α and IL-6.

Graphical abstract: Design and synthesis of novel oleanolic acid based chromenes as anti-proliferative and anti-inflammatory agents

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Publication details

The article was received on 18 Jul 2018, accepted on 24 Aug 2018 and first published on 03 Sep 2018


Article type: Paper
DOI: 10.1039/C8NJ03564D
Citation: New J. Chem., 2018,42, 16782-16794
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    Design and synthesis of novel oleanolic acid based chromenes as anti-proliferative and anti-inflammatory agents

    D. S. Raghuvanshi, N. Verma, S. Singh, S. Luqman, A. Chand Gupta, D. U. Bawankule, S. Tandon, A. Nagar, Y. Kumar and F. Khan, New J. Chem., 2018, 42, 16782
    DOI: 10.1039/C8NJ03564D

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