Synthesis, stereochemistry and cytotoxic activity of novel steroidal 16-spiro-1,3,2-dioxaphosphorinanes

被引：6
|
作者：
Woelfling, Janos [1 ]
Kovacs-Penzes, Piroska [1 ,2 ]
Zupko, Istvan [3 ]
Schneider, Gyula [1 ]
Frank, Eva [1 ]
机构：
[1] Univ Szeged, Dept Organ Chem, H-6720 Szeged, Hungary
[2] Glycom AS, DK-2800 Lyngby, Denmark
[3] Univ Szeged, Dept Pharmacodynam & Biopharm, H-6720 Szeged, Hungary
来源：
JOURNAL OF MOLECULAR STRUCTURE | 2012年 / 1013卷
基金：
匈牙利科学研究基金会;
关键词：
Steroids; Spiro compounds; Phosphorylations; Dioxaphosphorinanes; Stereostructure; Antiproliferative effect; P-HETEROCYCLES; CHAIR; CONFORMATION; H-1-NMR; DESIGN; SERIES; P-31;
D O I：
10.1016/j.molstruc.2012.01.013
中图分类号：
O64 [物理化学（理论化学）、化学物理学];
学科分类号：
070304 ; 081704 ;
摘要：
The epimeric pairs a and b of novel steroidal 16-spiro-dioxaphosphorinanes 4-8 were synthetized via the phosphorylation of 16,16-bis(hydroxymethyl)androst-4-ene-3,17-dione (2) and their stereostructures were investigated by NMR methods. The dioxaphosphorinane moiety exists mainly as one of the possible chair conformers or as a chair twist equilibrium in solution as a consequence of the rigidity of the sterane framework. The contributions of the conformers depend strongly on the configuration of the P atom and the stereoelectronic properties of the substituents on it. The antiproliferative activities of the structurally related products were determined in vitro with the MTT assay on three malignant human cell lines (HeLa, MCF7 and A431). (C) 2012 Elsevier B.V. All rights reserved.
引用
收藏
页码：39 / 44
页数：6
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