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炔黄酮衍生物的合成、X射线晶体结构及生物学性质

Synthesis, X-ray crystal structure and biological properties of acetylenic flavone derivatives.

作者信息

Artali Roberto, Barili Pier Luigi, Bombieri Gabriella, Re Paolo Da, Marchini Nicoletta, Meneghetti Fiorella, Valenti Piero

机构信息

Istituto di Chimica Farmaceutica e Tossicologica, Universita di Milano, Viale Abruzzi, 42, I-20131 Milan, Italy.

出版信息

Farmaco. 2003 Sep;58(9):875-81. doi: 10.1016/S0014-827X(03)00145-9.

DOI:10.1016/S0014-827X(03)00145-9
PMID:13679182
Abstract

The reactions of iodoflavone with 3-methyl-3-hydroxybut-1-yne and 3-methylbut-3-en-2-yne are described and the antimicrobial and cytotoxic activities of the obtained compounds have been tested. The molecular structures of 6-(3-hydroxy-3-methylbut-1-ynyl)-flavone (1a) and 6-(3-methylbut-3-en-1-ynyl) flavone (1b) have been determined by X-ray crystallography. The planar configuration of the two compounds has been attributed to intramolecular hydrogen bond interactions. In 1a, the presence of the hydroxyl group determines a dimeric arrangement of the molecules. In both compounds in the crystal state, molecular stacking has been observed.

摘要

描述了碘黄酮与3-甲基-3-羟基丁-1-炔和3-甲基丁-3-烯-2-炔的反应,并测试了所得化合物的抗菌和细胞毒性活性。通过X射线晶体学确定了6-(3-羟基-3-甲基丁-1-炔基)黄酮(1a)和6-(3-甲基丁-3-烯-1-炔基)黄酮(1b)的分子结构。这两种化合物的平面构型归因于分子内氢键相互作用。在1a中,羟基的存在决定了分子的二聚排列。在晶体状态下的两种化合物中,均观察到了分子堆积。

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