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Molecules 2007, 12(5), 1101-1116; doi:10.3390/12051101

Synthesis and Cytotoxic Activity of Some 3-Benzyl-5-Arylidenefuran-2(5H)-ones

1, 1,* , 1, 1, 3, 3, 3 and 3
1 Department of Chemistry, Federal University of Viçosa, Av. P.H. Rolfs, S/N, CEP 36570-000, Viçosa, MG, Brazil 2 Department of Chemistry, Federal University of Minas Gerais, Av. Antônio Carlos, 6627, CEP 31270-901, Belo Horizonte, MG, Brazil 3 Department of Physiology and Pharmacology, Federal University of Ceará, Rua Coronel Nunes de Melo, 1127, CEP 60431-970, Fortaleza, CE, Brazil
* Author to whom correspondence should be addressed.
Received: 26 April 2007 / Revised: 21 May 2007 / Accepted: 21 May 2007 / Published: 24 May 2007
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3-Benzyl-furan-2(5H)-one (2a) and 3-(4-bromobenzyl)-furan-2(5H)-one (2b) were treated with TBDMSOTf and converted into the corresponding tert-butyldimethyl-silylfuran ethers. These furans were further condensed with several aromatic aldehydes affording compounds 5-14 with general 3-benzyl-5-arylidene-furan-2(5H)-one structures in 31% to 98% yields. Such compounds are analogues of the naturally occurring nostoclide lactones, reported to present moderate cytotoxic activity. Compounds 5-14 were submitted to an in vitro bioassay against the HL-60, HCT-8, SF295 and MDA-MB-435 cancer cell lines using the MTT cytotoxicity assay.
Keywords: Nostoclides; cytotoxic activity; lactones; γ-alkylidenebutenolides Nostoclides; cytotoxic activity; lactones; γ-alkylidenebutenolides
This is an open access article distributed under the Creative Commons Attribution License (CC BY) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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Teixeira, R.R.; Barbosa, L.C.; Maltha, C.R.A.; Rocha, M.E.; Bezerra, D.P.; Costa-Lotuf, L.V.; Pessoa, C.; Moraes, M.O. Synthesis and Cytotoxic Activity of Some 3-Benzyl-5-Arylidenefuran-2(5H)-ones. Molecules 2007, 12, 1101-1116.

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