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Populene D Analogues: Design, Concise Synthesis and Antiproliferative Activity
Instituto de Química, Universidade de São Paulo, Av. Prof. Lineu Prestes, 748, CP 26077, CEP São Paulo 05513-970, SP, Brazil
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; in revised form: 2 August 2012 / Accepted: 3 August 2012 / Published: 10 August 2012
Abstract: 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
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Reddy, K.R.K.K.; Longato, G.B.; Carvalho, J.E.; Ruiz, A.L.T.G.; Silva, Jr., L.F. Populene D Analogues: Design, Concise Synthesis and Antiproliferative Activity. Molecules 2012, 17, 9621-9630.
Reddy KRKK, Longato GB, Carvalho JE, Ruiz ALTG, Silva, Jr. LF. Populene D Analogues: Design, Concise Synthesis and Antiproliferative Activity. Molecules. 2012; 17(8):9621-9630.
Reddy, Kachi R. Kishore Kumar; Longato, Giovanna B.; Carvalho, João E. de; Ruiz, Ana L. T. G.; Silva, Jr., Luiz F. 2012. "Populene D Analogues: Design, Concise Synthesis and Antiproliferative Activity." Molecules 17, no. 8: 9621-9630.