populene d analogues design, concise synthesis and antiproliferative activitypopulene d类似物的设计、简洁的合成和抗增殖活动.pdfVIP
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populene d analogues design, concise synthesis and antiproliferative activitypopulene d类似物的设计、简洁的合成和抗增殖活动
Molecules 2012, 17, 9621-9630; doi:10.3390/molecule
OPEN ACCESS
molecules
ISSN 1420-3049
/journal/molecules
Article
Populene D Analogues: Design, Concise Synthesis and
Antiproliferative Activity
1 2 2
Kachi R. Kishore Kumar Reddy , Giovanna B. Longato , João E. de Carvalho ,
Ana L. T. G. Ruiz 2,* and Luiz F. Silva, Jr. 1,*
1 Instituto de Química, Universidade de São Paulo, Av. Prof. Lineu Prestes, 748, CP 26077,
CEP São Paulo 05513-970, SP, Brazil; E-Mail: kishorereddyk@
2 Divisão 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
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