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Molecules 2012, 17(8), 9621-9630; doi:10.3390/molecules17089621

Populene D Analogues: Design, Concise Synthesis and Antiproliferative Activity

2,*  and , Jr. 1,*
1 Instituto de Química, Universidade de São Paulo, Av. Prof. Lineu Prestes, 748, CP 26077, CEP São Paulo 05513-970, SP, Brazil 2 Divisão de Farmacologia e Toxicologia, Centro Pluridisciplinar de Pesquisas Químicas, Biológicas e Agrícolas (CPQBA), UNICAMP, CP6171, Campinas 13083-970, SP, Brazil
* Authors to whom correspondence should be addressed.
Received: 15 June 2012 / Revised: 2 August 2012 / Accepted: 3 August 2012 / Published: 10 August 2012
(This article belongs to the Section Organic Synthesis)
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An efficient and concise synthesis of nine populene D analogues was performed using an iodine-catalyzed Prins cyclization as the key transformation. The antiproliferative activity of these new pyrans against several cancer cell lines was then investigated. Among them, an isochromene with moderate activity (mean logGI50 = 0.91) was found. Additionally, compounds with selectivity toward the tumor cell lines NCI-ADR/RES, OVCAR-3, and HT29 were discovered.
Keywords: osochromene; pyrans; Prins cyclization; iodine; antiproliferative; cancer osochromene; pyrans; Prins cyclization; iodine; antiproliferative; cancer
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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Reddy, K.R.K.K.; Longato, G.B.; Carvalho, J.E.; Ruiz, A.L.T.G.; Silva, L.F., , Jr. Populene D Analogues: Design, Concise Synthesis and Antiproliferative Activity. Molecules 2012, 17, 9621-9630.

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