STEREOSPECIFIC SYNTHESIS AND ABSOLUTE-CONFIGURATION OF MEXILETINE

被引：33

作者：

FRANCHINI, C ^{[1
]}

CELLUCCI, C ^{[1
]}

CORBO, F ^{[1
]}

LENTINI, G ^{[1
]}

SCILIMATI, A ^{[1
]}

TORTORELLA, V ^{[1
]}

STASI, F ^{[1
]}

机构：

[1] UNIV BARI,DEPT GEOMINERAL,I-70126 BARI,ITALY

来源：

CHIRALITY | 1994年 / 6卷 / 07期

关键词：

ANTIARRHYTHMIC DRUG; MEXILETINE; ABSOLUTE CONFIGURATION; CHIROPTICAL PROPERTIES; X-RAY ANALYSIS;

D O I：

10.1002/chir.530060713

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Data on the absolute configuration of mexiletine (MEX) do not appear to have been published, although in several published reports the configuration is referred to as (-)-(R) and (+)-(S), based on information from manufacturers providing the drug stereoisomers. We demonstrate that (-)-MEX has the (R)-configuration by mean of a new stereospecific synthesis. X-Ray analysis of an optical active sample of (+)-MEX as its hydrobromide salt, obtained from chemical resolution of the racemic mixture, was carried out in order to obtain precise information on bond lengths and angles, useful for studies on structure-activity relationships. We also report the NMR analysis in presence of Eu(hfc)(3) as shift reagent, which represents a simple method for the determination of enantiomeric excess (ee) in addition to the well-known chiral HPLC methods. (C) 1994 Wiley-Liss, Inc.

引用

页码：590 / 595

页数：6

共 19 条

[1]

Abounassif M.A., 1991, ANAL PROFILES DRUG S, V20, P433

[2]

FRANCHINI C, 1991, 2ND INT S CHIR DISCR

[3] REVERSED-PHASE LC RESOLUTIONS OF CHIRAL ANTIARRHYTHMIC AGENTS VIA DERIVATIZATION WITH HOMOCHIRAL ISOTHIOCYANATES [J].