CONFORMATION OF THE NOOTROPIC AGENTS 1-(4-METHOXYBENZOYL)-5-OXO-2-PYRROLIDINEPROPANOIC ACID (CI-933) AND 4-HYDROXYMETHYL-1-BENZYL-PYRROLIDIN-2-ONE (WEB-1868) - X-RAY CRYSTAL-STRUCTURES, THEORETICAL MO CALCULATIONS (AM-1) AND 600 MHZ H-1-NMR SPECTRA

被引:7
作者
AMATO, ME
BANDOLI, G
DJEDAINI, F
DOLMELLA, A
GRASSI, A
PAPPALARDO, GC
机构
[1] UNIV CATANIA,DIPARTIMENTO SCI CHIM,VIALE A DORIA 6,I-95125 CATANIA,ITALY
[2] UNIV CATANIA,FAC FARM,CATTEDRA CHIM GEN,I-95125 CATANIA,ITALY
[3] UNIV PADUA,DIPARTIMENTO SCI FARMACEUT,I-35131 PADUA,ITALY
[4] CENS,DEPT PHYSIOCHIM,SCM,F-91191 GIF SUR YVETTE,FRANCE
关键词
D O I
10.1016/0022-2860(90)85055-N
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 crystal and molecular structures of the cognition activators 1-(4-methoxybenzoyl)-5-oxo-2-pyrrolidinepropanoic acid (CI-933) (1) and 4-hydroxymethyl-1-benzyl-pyrrolidin-2-one (WEB-1868) (2) have been determined by X-ray analysis. The conformations of the isolated molecules 1 and 2 have been deduced from AM1-type theoretical calculations. Whilst in 1 there are no hydrogen bonds, in 2 stabilization of the crystal occurs through effective inter- and intramolecular {A figure is presented} bonds. The five-membered ring in both 1 and 2 adopts an envelope conformation in the solid with C(3) at the flap displaced from the C(1), C(2), C(4), N(5) mean plane. Bond distances and angles are normal and comparable with previously known similar structures. In the crystal, the torsion angles C(1)-N(5)-C(6)-C(7) and N(5)-C(6)-C(7)-C(8) in 1 are 43.1° and 44.8°, respectively; the same torsion angles in 2 are -101° and 42°, respectively. Results of theoretical calculations correlate well with the conformation of 1 in the solid, whilst in the case of 2 these indicate that the conformation in the crystal should not be retained by the isolated molecule. The complete analysis of the very high field (600 MHz) 1H NMR spectra of both compounds in CDCl3, gives results well in line with the above established conformational features. © 1990.
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页码:487 / 502
页数:16
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