LFER AND COMFA STUDIES ON OPTICAL RESOLUTION OF ALPHA-ALKYL ALPHA-ARYLOXY ACETIC-ACID METHYL-ESTERS ON DACH-DNB CHIRAL STATIONARY-PHASE

被引：22

作者：

CAROTTI, A ^{[1
]}

ALTOMARE, C ^{[1
]}

CELLAMARE, S ^{[1
]}

MONFORTE, AM ^{[1
]}

BETTONI, G ^{[1
]}

LOIODICE, F ^{[1
]}

TANGARI, N ^{[1
]}

TORTORELLA, V ^{[1
]}

机构：

[1] UNIV MESSINA,DIPARTIMENTO FARMACOCHIM,I-98168 MESSINA,ITALY

来源：

JOURNAL OF COMPUTER-AIDED MOLECULAR DESIGN | 1995年 / 9卷 / 02期

关键词：

CHIRAL CHROMATOGRAPHY; ENANTIOSEPARATION; COMFA; 3D QSAR;

D O I：

10.1007/BF00124403

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

The HPLC resolution of a series of racemic ct-substituted a-aryloxy acetic acid methyl esters I on a pi-acid chiral stationary phase containing N,N'-(3,5-dinitrobenzoyl)-trans-1,2-diaminocylohexane as chiral selector was modelled by linear free energy-related (LFER) equations and comparative molecular field analysis (CoMFA). Our results indicate that the retention process mainly depends on solute lipophilicity and steric properties, whereas enantioselectivity is primarily influenced by electrostatic and steric interactions. CoMFA provided additional information with respect to the LFER study, allowed the mixing of different subsets of I and led to a quantitative 3D model of steric and electrostatic factors responsible for chiral recognition.

引用

页码：131 / 138

页数：8

共 41 条

[31]

SCOTT PPW, 1992, TECHNIQUES LIGAND CH, P141

[32]

STEVENSON D, 1989, CHIRAL SEPARATIONS

[33] ENANTIOMERIC SEPARATION OF SUBSTITUTED 2-ARYLOXY PROPIONIC ESTERS - APPLICATION TO THE DETERMINATION OF THE ENANTIOMERIC EXCESS IN HERBICIDE FORMULATIONS [J].

TAMBUTE, A ;

SIRET, L ;

CAUDE, M ;

ROSSET, R .

JOURNAL OF CHROMATOGRAPHY, 1991, 541 (1-2) :349-357

[34] RECOMMENDATIONS FOR COMFA STUDIES AND 3D QSAR PUBLICATIONS [J].

THIBAUT, U ;

FOLKERS, G ;

KLEBE, G ;

KUBINYI, H ;

MERZ, A ;

ROGNAN, D .

QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIPS, 1994, 13 (01) :1-3

[35]

VANDEWATERBEEMD H, 1985, ADV DRUG RES, V17, P85

[36]

Verloop A., 1987, STERIMOL APPROACH DR

[37]

Vogtle F., 1991, SUPRAMOLECULAR CHEM

[38]

WAINER LW, 1993, DRUG STEREOCHEMISTRY

[39] BIOLOGICAL SIGNIFICANCE OF THE ENANTIOMERIC PURITY OF DRUGS [J].

WALDECK, B .

CHIRALITY, 1993, 5 (05) :350-355

[40] USING THEORETICAL DESCRIPTORS IN QUANTITATIVE STRUCTURE-ACTIVITY-RELATIONSHIPS - SOME TOXICOLOGICAL INDEXES [J].

WILSON, LY ;

FAMINI, GR .

JOURNAL OF MEDICINAL CHEMISTRY, 1991, 34 (05) :1668-1674

← 1 2 3 4 5 →