Synthesis and reactions of Biginelli compounds, part 19 - X-ray structure, conformational analysis, enantioseparation, and determination of absolute configuration of the mitotic kinesin Eg5 inhibitor monastrol

被引:194
作者
Kappe, CO
Shishkin, OV
Uray, G
Verdino, P
机构
[1] Karl Franzens Univ Graz, Inst Chem, A-8010 Graz, Austria
[2] Natl Acad Sci Ukraine, STC Inst Single Crystals, Dept Alkali Halide Crystals, UA-310072 Kharkov, Ukraine
基金
奥地利科学基金会;
关键词
Biginelli reactions; enantiomeric purity; circular dichroism; conformation;
D O I
10.1016/S0040-4020(00)00116-2
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The conformational features of the mitotic kinesin Eg5 inhibitor monastrol were investigated by computational (AM1, HF/3-21G*), X-ray diffraction, and NMR studies showing that monastrol is a conformationally highly flexible molecule. Racemic monastrol was resolved by direct enantioselective HPLC and thr absolute configuration of the first eluting (S)-(+) enantiomer was established by CD spectroscopy. (C) 2000 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:1859 / 1862
页数:4
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