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Molecules 2014, 19(6), 7881-7900; doi:10.3390/molecules19067881

Synthesis and Cytotoxic Activity of a New Group of Heterocyclic Analogues of the Combretastatins

1
Laboratory of Medicinal Chemistry, Novosibirsk Institute of Organic Chemistry, Siberian Branch, Russian Academy of Sciences, Lavrentjev Avenue 9, Novosibirsk 630090, Russia
2
Medicinal Department, Novosibirsk State University, Pirogova St. 2, Novosibirsk 630090, Russia
*
Author to whom correspondence should be addressed.
Received: 15 April 2014 / Revised: 3 June 2014 / Accepted: 5 June 2014 / Published: 11 June 2014
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Abstract

A series of new analogs of combretastatin A-4 (CA-4, 1) with the A or B-ring replaced by a 3-oxo-2,3-dihydrofurocoumarin or a furocoumarin residue have been designed and synthesized by employing a cross-coupling approach. All the compounds were evaluated for their cytotoxic activity with respect to model cancer cell lines (CEM-13, MT-4, U-937) using conventional MTT assays. Structure-activity relationship analysis reveals that compounds 2, 3, 68 in which the (Z)-styryl substituent was connected to the 2-position of the 3-oxo-2,3-dihydrofurocoumarin core, demonstrated increased potency compared to 3-(Z)-styrylfurocoumarins 4, 5, 911. The methoxy-, hydroxyl- and formyl- substitution on the aromatic ring of the (Z)-styryl moiety seems to play an important role in this class of compounds. Compounds 2 and 3 showed the best potency against the CEM-13 cell lines, with CTD50 values ranging from 4.9 to 5.1 μM. In comparison with CA-4, all synthesized compounds presented moderate cytotoxic activity to the T-cellular human leucosis cells MT-4 and lymphoblastoid leukemia cells CEM-13, but most of them were active in the human monocyte cell lines U-937. View Full-Text
Keywords: furocoumarins; oreoselone; psoralen; Sonogashira coupling; semi-hydrogenation; combretastatins; cytotoxicity furocoumarins; oreoselone; psoralen; Sonogashira coupling; semi-hydrogenation; combretastatins; cytotoxicity
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This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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MDPI and ACS Style

Lipeeva, A.V.; Shults, E.E.; Shakirov, M.M.; Pokrovsky, M.A.; Pokrovsky, A.G. Synthesis and Cytotoxic Activity of a New Group of Heterocyclic Analogues of the Combretastatins. Molecules 2014, 19, 7881-7900.

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