Synthesis of Fluorinated Brassinosteroids Based on Alkene Cross-Metathesis and Preliminary Biological Assessment

被引：33

作者：

Eignerova, Barbara ^{[1
,2
]}

Slavikova, Barbora ^{[2
]}

Budesinsky, Milos ^{[2
]}

Dracinsky, Martin ^{[2
]}

Klepetarova, Blanka ^{[2
]}

St'astna, Eva ^{[2
]}

Kotora, Martin ^{[1
,2
]}

机构：

[1] Charles Univ Prague, Dept Organ & Nucl Chem, Fac Sci, Prague 12843 2, Czech Republic

[2] Inst Organ Chem & Biochem AS CR, Prague 16610 6, Czech Republic

来源：

JOURNAL OF MEDICINAL CHEMISTRY | 2009年 / 52卷 / 18期

关键词：

PERFLUOROALKYL IODIDES; MEDICINAL CHEMISTRY; OLEFIN METATHESIS; BRASSICA-NAPUS; PART; ANTICANCER; ANALOGS; ALLOPREGNANOLONE; DERIVATIVES; EFFICIENT;

D O I：

10.1021/jm900495f

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Three types of brassinosteroid analogues with perfluoroalkylated side chains were synthesized by using alkene cross-metathesis of a brassinosteroid derivative bearing a terminal alkene moiety with different (perfluoroalkyl)propenes. The presence of the double bonds in the cross-metathesis products allowed a facile one-step double dihydroxylation to provide intermediates that after Baeyer-Villiger oxidation afforded the target compounds. Biological activity of the prepared analogues was tested in GABA(A) receptor, cytotoxic, and brassinolide activity, which reached in some cases the same range as their nonfluorinated analogues,

引用

页码：5753 / 5757

页数：5

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