Oxcarbazepine: structure and anticonvulsant activity

被引:20
作者
Hempel, A
Camerman, N
Camerman, A
Mastropaolo, D
机构
[1] Univ Toronto, Dept Biochem, Toronto, ON M5S 1A8, Canada
[2] Ardono Res, Bellevue, WA 98004 USA
关键词
D O I
10.1107/S1600536805010676
中图分类号
O7 [晶体学];
学科分类号
0702 ; 070205 ; 0703 ; 080501 ;
摘要
In the crystal structure of the title compound, 10-oxo-10,11-dihydro-5H-dibenzo[b,f]azepine-5-carboxamide, C15H12N2O2, the azepine seven-membered ring adopts a classical but slightly twisted boat conformation, forcing the molecule to adopt a butterfly shape. In addition to one normal hydrogen bond, two non-standard weak hydrogen bonds of the C-H center dot center dot center dot O type also contribute to the molecular arrangement in the crystal structure. Stereochemical comparison with phenytoin indicates that oxcarbazepine may utilize the same mechanism for its anticonvulsant activity.
引用
收藏
页码:O1313 / O1315
页数:3
相关论文
共 11 条
[1]   CONFORMATION OF 6-MEMBERED RINGS [J].
BOEYENS, JCA .
JOURNAL OF CRYSTAL AND MOLECULAR STRUCTURE, 1978, 8 (06) :317-320
[2]   ON THE CRYSTALLOGRAPHY AND STEREOCHEMISTRY OF ANTI-EPILEPTIC DRUGS [J].
CAMERMAN, A ;
CAMERMAN, N .
ACTA CRYSTALLOGRAPHICA SECTION B-STRUCTURAL SCIENCE, 1981, 37 (SEP) :1677-1679
[3]   STEREOCHEMICAL BASIS OF ANTICONVULSANT DRUG ACTION .1. CRYSTAL AND MOLECULAR STRUCTURE OF DIPHENYLHYDANTOIN, A NONCENTROSYMMETRIC STRUCTURE SOLVED BY CENTRIC SYMBOLIC ADDITION [J].
CAMERMAN, A ;
CAMERMAN, N .
ACTA CRYSTALLOGRAPHICA SECTION B-STRUCTURAL CRYSTALLOGRAPHY AND CRYSTAL CHEMISTRY, 1971, B 27 (NOV15) :2205-&
[4]   GENERAL DEFINITION OF RING PUCKERING COORDINATES [J].
CREMER, D ;
POPLE, JA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1975, 97 (06) :1354-1358
[6]   THE STRUCTURE OF 10,11-DIHYDRO-10-HYDROXY-5H-DIBENZ[B,F]AZEPINE-5-CARBOXAMIDE, AN ANTICONVULSANT DRUG MOLECULE [J].
LISGARTEN, JN ;
PALMER, RA ;
SALDANHA, JW .
ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1989, 45 :656-658
[7]   A SEMI-EMPIRICAL METHOD OF ABSORPTION CORRECTION [J].
NORTH, ACT ;
PHILLIPS, DC ;
MATHEWS, FS .
ACTA CRYSTALLOGRAPHICA SECTION A-CRYSTAL PHYSICS DIFFRACTION THEORETICAL AND GENERAL CRYSTALLOGRAPHY, 1968, A 24 :351-&
[8]  
PICKER, 1967, PICKER OPERATING MAN
[9]  
Sheldrick G. M., 1997, SHELXS 97 PROGRAM CR
[10]   Unrolling the hydrogen bond properties of C-H center dot center dot center dot O interactions [J].
Steiner, T .
CHEMICAL COMMUNICATIONS, 1997, (08) :727-734