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Molecules 2013, 18(2), 1881-1896; doi:10.3390/molecules18021881

Synthesis and Antiproliferative Activity of C-3 Functionalized Isobenzofuran-1(3H)-ones

1,* , 2,* , 1, 2, 1 and 1
1 Departamento de Química, Universidade Federal de Viçosa, Av. P.H. Rolfs, S/N, CEP 36.570-000, Viçosa, MG, Brazil 2 Departamento de Bioquímica e Biologia Molecular, Universidade Federal de Viçosa, Av. P.H. Rolfs, S/N, CEP 36.570-000, Viçosa, MG, Brazil
* Authors to whom correspondence should be addressed.
Received: 25 October 2012 / Revised: 20 December 2012 / Accepted: 24 December 2012 / Published: 1 February 2013
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A series of thirteen C-3 functionalized isobenzofuran-1(3H)-ones (phtalides) was synthesized via condensation, aromatization, and acetylation reactions. NMR (one and two dimensional experiments), IR, and mass spectrometry analysis allowed confirmation of the identity of the synthesized compounds. The substances were submitted to in vitro bioassays against U937 (lymphoma) and K562 (myeloid leukemia) cancer cell lines using the MTT cytotoxicity assay. Some derivatives inhibited 90% of cell viability at 100 µM. Also, two phtalides presented biological activity superior than that of etoposide (VP16), a commercial drug used as a positive control in the assays. In silico drug properties of the evaluated compounds were calculated and the results are discussed.
Keywords: isobenzofuran-1(3H)-one; phtalides; antiproliferative activity isobenzofuran-1(3H)-one; phtalides; antiproliferative activity
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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Teixeira, R.R.; Bressan, G.C.; Pereira, W.L.; Ferreira, J.G.; de Oliveira, F.M.; Thomaz, D.C. Synthesis and Antiproliferative Activity of C-3 Functionalized Isobenzofuran-1(3H)-ones. Molecules 2013, 18, 1881-1896.

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