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Stereoselective synthesis of carbohydrate fused pyrano[3,2-c]pyranones as anticancer agents

Abstract

Pyrano[3,2-c]pyranone is an important structural motif present in many natural products exhibiting diverse biological activities. Two series of carbohydrate fusedpyrano[3,2-c]pyranone derivatives (n = 20) were efficiently synthesized starting from 2-C–formyl galactal and 2-C–formyl glucal, reacting with various 4-hydroxycoumarins in very short reaction time (10 min) under microwave assisted condition. Anticancer activity of these synthesized pyrano[3,2-c]pyranones were determined in detail through cellular assays against MCF-7 (breast), MDA-MB-231 (breast) and HepG2 (liver) cancer cell lines. The newly synthesized pyrano[3,2-c]pyranones were screened for their cell-viability and anti-proliferative activity against MCF-7, MDA-MB-231 and HepG2 cell lines. The compounds 12, 13 and 14 exhibited high growth inhibitory potencies selectively against MCF-7 cell with half maximal inhibitory concentration (IC50) values 19.9, 14.5 and 10.9 µM respectively. The compounds 12, 13, 14, 15 and 19 inhibited cell growth of MDA-MB-231 cell (breast) by 43, 44, 37, 31 and 45% respectively. However, no inhibitory effect was observed by these compounds in human liver cancer cell line (HepG2) and normal cell lines (HEK293, human embryonic kidney cells). Mechanistic studies showed that, these compounds alter cell morphology and cause G2/M arrest in MCF-7. Further study showed compounds 12, 13 and 14 significantly inhibited cell migration which was accompanied by altered microtubule distribution. An enhanced accumulation of these compounds in cells was observed as compared to 4-hydroxycoumarins precursor in intracellular uptake assay. These findings confirms that, carbohydrate fused pyrano[3,2-c]pyranone are better candidates for anticancer activity.

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Publication details

The article was received on 21 Mar 2018, accepted on 08 Jul 2018 and first published on 09 Jul 2018


Article type: Paper
DOI: 10.1039/C8NJ01395K
Citation: New J. Chem., 2018, Accepted Manuscript
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    Stereoselective synthesis of carbohydrate fused pyrano[3,2-c]pyranones as anticancer agents

    R. Sagar, P. Kumari, S. Gupta, C. Narayana, S. Ahmad and S. Singh, New J. Chem., 2018, Accepted Manuscript , DOI: 10.1039/C8NJ01395K

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