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synthesis and cytotoxic activity of some 3-benzyl-5-arylidenefuran-2(5h)-ones合成和细胞毒性的活动有些3-benzyl-5-arylidenefuran-2(5 h)的.pdf

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Molecules 2007, 12, 1101-1116 molecules ISSN 1420-3049 © 2007 by MDPI /molecules Full Paper Synthesis and Cytotoxic Activity of Some 3-Benzyl-5-Arylidenefuran-2(5H)-ones Róbson Ricardo Teixeira 1,2, Luiz Cláudio Almeida Barbosa 1,*, Célia Regina Alvares Maltha 1, Marcelo Eça Rocha 1, Daniel Pereira Bezerra 3, Letícia Veras Costa-Lotufo 3, Cláudia Pessoa 3 3 and Manoel Odorico Moraes 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; E-mail: lcab@ufv.br; Tel.: (+55) 31 3899 3068; Fax: (+55) 31 3899 3065 Received: 26 April 2007; in revised form: 21 May 2007 / Accepted: 21 May 2007 / Published: 24 May 2007 Abstract: 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
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