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Populene D Analogues Design, Concise Synthesis and Antiproliferative Activity 英文参考文献
Molecules 2012, 17, 9621-9630; doi:10.3390/moleculeOPEN ACCESS
molecules
ISSN 1420-3049
/journal/molecules
Article
Populene D Analogues: Design, Concise Synthesis and
Antiproliferative Activity
Kachi R. Kishore Kumar Reddy 1, Giovanna B. Longato 2, Jo?o E. de Carvalho 2,
Ana L. T. G. Ruiz 2,* and Luiz F. Silva, Jr. 1,*
1
Instituto de Química, Universidade de S?o Paulo, Av. Prof. Lineu Prestes, 748, CP 26077,
CEP S?o Paulo 05513-970, SP, Brazil; E-Mail: kishorereddyk@
2
Divis?o de Farmacologia e Toxicologia, Centro Pluridisciplinar de Pesquisas Químicas,
Biológicas e Agrícolas (CPQBA), UNICAMP, CP6171, Campinas 13083-970, SP, Brazil;
E-Mails: giovannabl@.br (G.B.L.); carvalho@cpqba.unicamp.br (J.E.C.)
* Authors to whom correspondence should be addressed;
E-Mails: analucia@cpqba.unicamp.br (A.L.T.G.R.); luizfsjr@iq.usp.br (L.F.S.J.);
Tel.: +55-11-3091-2388 (L.F.S.J.); Fax: +55-11-3815-5579 (L.F.S.J.).
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
1. Introduction
Natural products have always played an important role in drug discovery [1–5]. Although it is not
always possible to understand the exact function of the secondary metabolites isolated from natural
sources, they are often used as inspiration for new drugs, particularly in the area of cancer [6–9]. The
pyran subunit can be frequently recog
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