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Issue 12, 2018
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Stereoselective synthesis of natural product inspired carbohydrate fused pyrano[3,2-c]quinolones as antiproliferative agents

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Abstract

Pyrano[3,2-c]quinolone structural motifs are commonly found in natural products with diverse biological activities. As part of a research programme aimed at developing the efficient synthesis of natural product-like small molecules, we designed and developed the microwave assisted, facile stereoselective synthesis of two series of carbohydrate fused pyrano[3,2-c]quinolone derivatives (n = 23) starting from 2-C-formyl galactal and 2-C-formyl glucal, reacting with various 4-hydroxyquinolones in shorter reaction times (15–20 min). The antiproliferative activity of these synthesized pyrano[3,2-c]quinolones was determined against MCF-7 (breast) and HepG2 (liver) cancer cells. The selected library members displayed low micromolar (3.53–9.68 μM) and selective antiproliferative activity. These findings on carbohydrate fused pyrano[3,2-c]quinolone derivatives are expected to provide new leads for anticancer drug discovery.

Graphical abstract: Stereoselective synthesis of natural product inspired carbohydrate fused pyrano[3,2-c]quinolones as antiproliferative agents

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Publication details

The article was received on 27 Dec 2017, accepted on 31 Jan 2018 and first published on 31 Jan 2018


Article type: Paper
DOI: 10.1039/C7OB03186F
Citation: Org. Biomol. Chem., 2018,16, 2049-2059
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    Stereoselective synthesis of natural product inspired carbohydrate fused pyrano[3,2-c]quinolones as antiproliferative agents

    P. Kumari, C. Narayana, S. Dubey, A. Gupta and R. Sagar, Org. Biomol. Chem., 2018, 16, 2049
    DOI: 10.1039/C7OB03186F

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