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Bioorg Med Chem Lett. 2012 Mar 1;22(5):1995-9. doi: 10.1016/j.bmcl.2012.01.033. Epub 2012 Jan 21.

A domino Knoevenagel hetero-Diels-Alder reaction for the synthesis of polycyclic chromene derivatives and evaluation of their cytotoxicity.

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  • 1Natural Product Chemistry, Indian Institute of Chemical Technology, Hyderabad 500 007, India.

Abstract

A novel octahydrochromeno[4,3-a]xanthen-1(2H)-one derivatives has been prepared using 10mol% dl-proline in ethanol via a domino Knoevenagel hetero-Diels-Alder reaction of alkene-tethered chromene-3-carboxaldehyde with cyclic 1,3-diketones. This is not only the first example on the preparation of highly diastereoselective pentacyclic chromene derivatives from alkene appended chromene-3-carboxaldehyde in one-pot process at ambient temperature but also preliminary evaluation of the cytotoxic activity of these chromene derivatives. Some of these compounds are found to exhibit potent cytotoxicity against two carcinoma cell lines A549 and B-16.

PMID:
22330634
DOI:
10.1016/j.bmcl.2012.01.033
[PubMed - indexed for MEDLINE]
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