Design and synthesis of novel oleanolic acid based chromenes as anti-proliferative and anti-inflammatory agents. (19th September 2018)

• Record Type: Journal Article
• Authors: Raghuvanshi, Dushyant Singh; Verma, Narsingh; Singh, Shilpi; Luqman, Suaib; Chand Gupta, Amit; Bawankule, Dnyaneshwar U.; Tandon, Sudeep; Nagar, Abhishek; Kumar, Yogesh; Khan, Feroz
• Is Part Of: New journal of chemistry. Volume 42:Number 20(2018)
• Page Start: 16782
• Page End: 16794
• Publication Date: 2018-09-19
• Subjects: Chemistry -- Periodicals; Chimie -- Périodiques; 540
• DOI: 10.1039/c8nj03564d
• Languages: English
• ISSNs: 1144-0546

Abstract

Abstract : A novel approach has been developed for the synthesis of oleanolic acid based anti-proliferative and anti-inflammatory chromenes. 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. Compounds6e, 6k, 7e and7g showed significant anticancer activity within the IC50 range of 12.23–39.04 μg mL −1 . The promising derivatives7e and7g were further analyzed for their effects on the cell cycle and apoptosis in A-549 and MDA-MB-231 cells, and it was depicted that7e and7g 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 analogue7g occurred through microtubule destabilization (IC50 : ∼3.6 μg mL −1 ), and it was found to be non-toxic against human erythrocytes. The compounds7e and7g significantly inhibited the proinflammatory cytokines TNF-α and IL-6.