NMR-STUDIES OF DRUGS - CHIRAL SOLVATING AGENTS FOR DIRECT DETERMINATION OF ENANTIOMERIC EXCESS OF THE CARDIAC ANTIARRHYTHMIC, MEXILETINE

被引:4
|
作者
ABOULENEIN, HY
ROTHCHILD, R
SINNEMA, A
机构
[1] CUNY JOHN JAY COLL CRIMINAL JUSTICE,DEPT SCI,TOXICOL RES & TRAINING CTR,NEW YORK,NY 10019
[2] DELFT UNIV TECHNOL,FAC CHEM TECHNOL & MAT SCI,ORGAN CHEM & CATALYSIS LAB,2628 BL DELFT,NETHERLANDS
关键词
OPTICAL PURITY; ENANTIOMER; ANALYSIS; 1-(2,6-DIMETHYLPHENOXY)-2-PROPANAMINE; ANTIARRHYTHMIC; CYCLODEXTRIN; ALPHA-METHOXY-ALPHA-(TRIFLUOROMETHYL) PHENYLACETIC ACID; MTPA; 2,2,2-TRIFLUORO-1-(9-ANTHRYL)ETHANOL; TFAE;
D O I
10.1080/00387019208017870
中图分类号
O433 [光谱学];
学科分类号
0703 ; 070302 ;
摘要
The 400 MHz H-1 NMR spectra of the cardiac antiarrhythmic, mexiletine, 1, have been studied with different chiral solvating agents (CSA) to obtain a very promising method for direct determination of enantiomeric excess (e.e.) with limited amounts of 1. The methods included the use of beta-cyclodextrin (beta-CD), gamma-cyclodextrin (gamma-CD), alpha-methoxy-alpha-(trifluoromethyl)phenylacetic acid (MTPA), and 2,2,2-trifluoro-1-(9-anthryl)ethanol (TFAE) . Use of TFAE in CDCl3 with the free base of 1 appeared to give the best results, with enantiomeric shift differences observed for the signals of the sidechain methyl, CH3CH, and the aryl methyls.
引用
收藏
页码:1367 / 1385
页数:19
相关论文
共 50 条
  • [1] 1H-NMR determination of the enantiomeric excess of the antiarrhythmic drug Mexiletine by using mandelic acid analogues as chiral solvating agents
    Carbonara, G
    Carocci, A
    Fracchiolla, G
    Franchini, C
    Lentini, G
    Loiodice, F
    Tortorella, P
    ARKIVOC, 2004, : 5 - 25
  • [2] NMR-STUDIES OF DRUGS - APPLICATION OF A CHIRAL LANTHANIDE SHIFT-REAGENT FOR POTENTIAL DIRECT DETERMINATION OF ENANTIOMERIC EXCESS OF METHSUXIMIDE
    REIFSNEIDER, RJ
    HOFFMAN, BH
    VENKATASUBBAN, KS
    ROTHCHILD, R
    MARTIN, R
    SPECTROSCOPY LETTERS, 1991, 24 (10) : 1373 - 1394
  • [3] 1H-NMR studies of drugs with chiral solvating agent:: The direct enantiomeric purity determination of the chiral anesthetic, prilocaine
    Hanna, GM
    ENANTIOMER, 2000, 5 (3-4): : 303 - 312
  • [4] Efficient and rapid determination of the enantiomeric excess of drugs with chiral solvating agents: carvedilol, fluoxetine and a precursor of diarylether lactams
    Perez-Trujillo, Miriam
    Virgili, Albert
    TETRAHEDRON-ASYMMETRY, 2006, 17 (20) : 2842 - 2846
  • [5] Macrocyclic Compound as NMR Chiral Solvating Agent for Determination of Enantiomeric Excess of Carboxylic Acids
    Yang, Xiao-feng
    Ning, Rui
    Xie, Li-jun
    Cui, Yu
    Zhang, Yong-ling
    Zheng, Lu-yi
    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 2013, 86 (08) : 987 - 989
  • [6] The novel macrocyclic compounds as chiral solvating agents for determination of enantiomeric excess of carboxylic acids
    Ma, Fengnian
    Shen, Xiumin
    Ming, Xin
    Wang, Junmei
    Jie Ou-Yang
    Zhang, Cong
    TETRAHEDRON-ASYMMETRY, 2008, 19 (13) : 1576 - 1586
  • [7] Chiral bis(amino amides) as chiral solvating agents for enantiomeric excess determination of α-hydroxy and arylpropionic acids
    Altava, Belen
    Burguete, M. Isabel
    Carbo, Noelia
    Escorihuela, Jorge
    Luis, Santiago V.
    TETRAHEDRON-ASYMMETRY, 2010, 21 (08) : 982 - 989
  • [8] Permethylated cyclodextrins as chiral solvating agents for the determination of the enantiomeric composition of apolar substrates by NMR
    Uccello-Barretta, G.
    Balzano, F.
    Cuzzola, A.
    Menicagli, R.
    Gazzetta Chimica Italiana, 127 (07):
  • [9] NMR-STUDIES OF DRUGS - ENANTIOMERIC EXCESS DETERMINATION OF N-ACETYLCATHINONE WITH EU(HFC)3
    BENSHAFRUT, R
    ROTHCHILD, R
    SPECTROSCOPY LETTERS, 1992, 25 (07) : 1097 - 1120
  • [10] Permethylated cyclodextrins as chiral solvating agents for the determination of the enantiomeric composition of apolar substrates by NMR
    Uccello-Barretta, G
    Balzano, F
    Cuzzola, A
    Menicagli, R
    Caporusso, AM
    Salvadori, P
    GAZZETTA CHIMICA ITALIANA, 1997, 127 (07): : 383 - 386