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

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

Róbson Ricardo Teixeira 1,* email, Gustavo Costa Bressan 2,* email, Wagner Luiz Pereira 1 , Joana Gasperazzo Ferreira 2 , Fabrício Marques de Oliveira 1  and Deborah Campos Thomaz 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; in revised form: 20 December 2012 / Accepted: 24 December 2012 / Published: 1 February 2013
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Abstract: 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

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MDPI and ACS Style

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.

AMA Style

Teixeira RR, Bressan GC, Pereira WL, Ferreira JG, de Oliveira FM, Thomaz DC. Synthesis and Antiproliferative Activity of C-3 Functionalized Isobenzofuran-1(3H)-ones. Molecules. 2013; 18(2):1881-1896.

Chicago/Turabian Style

Teixeira, Róbson R.; Bressan, Gustavo C.; Pereira, Wagner L.; Ferreira, Joana G.; de Oliveira, Fabrício M.; Thomaz, Deborah C. 2013. "Synthesis and Antiproliferative Activity of C-3 Functionalized Isobenzofuran-1(3H)-ones." Molecules 18, no. 2: 1881-1896.

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