Synthesis of novel steroid analogues containing nitrile and disulfide moieties via palladium-catalyzed cross-coupling reactions

被引：7
|
作者：
Mayer, Christoph D. [1 ]
Allmendinger, Lars [1 ]
Bracher, Franz [1 ]
机构：
[1] Univ Munich, Dept Pharm, Zentrum Pharmaforsch, D-81377 Munich, Germany
来源：
TETRAHEDRON | 2012年 / 68卷 / 06期
关键词：
Secosteroid; Cross-coupling reaction; Nitrile; Disulfide; CYTOTOXIC ACTIVITY; WITHANOLIDES; DESIGN; ADDUCT;
D O I：
10.1016/j.tet.2011.11.076
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Grundmann's ketone (3) was used as a common building block for introduction of the C+D) ring motif of steroids to prepare series of novel secosteroids containing nitrile or disulfide functionalities. Key steps in synthesis of these novel steroid analogues are palladium-catalyzed cross-coupling reactions. All target compounds were characterized by comprehensive analysis; in particular the stereochemical assignments of dinitriles 12a and 12b could be carried out in detail by NMR experiments. The pharmacological potential of all compounds was initially verified by a cytotoxicity test. (C) 2011 Elsevier Ltd. All rights reserved.
引用
收藏
页码：1810 / 1818
页数：9
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