Assessing the stable conformations of ibuprofen in solution by means of Residual Dipolar Couplings

被引：13

作者：

Di Pietro, Maria Enrica ^{[1
]}

Celebre, Giorgio ^{[1
]}

Aroulanda, Christie ^{[2
]}

Merlet, Denis ^{[2
]}

De Luca, Giuseppina ^{[1
]}

机构：

[1] Univ Calabria, Dipartimento Chim & Tecnol Chim, Lab LKNMR SCAn, Via P Bucci, I-87036 Arcavacata Di Rende, CS, Italy

[2] Univ Paris Saclay, Univ Paris Sud, UMR 8182, Equipe RMN Milieu Oriente,ICMMO, 15 Rue Georges Clemenceau, F-91405 Orsay, France

来源：

EUROPEAN JOURNAL OF PHARMACEUTICAL SCIENCES | 2017年 / 106卷

关键词：

Non-steroidal anti-inflammatory drugs; NMR spectroscopy; Alignment media; Conformational surface; LIQUID-CRYSTAL NMR; NONSTEROIDAL ANTIINFLAMMATORY DRUGS; INFORMATION-CONTENT; SPECTROSCOPY; SOLVENTS; NAPROXEN; ENERGY; ACIDS; (R)-IBUPROFEN; DERIVATIVES;

D O I：

10.1016/j.ejps.2017.05.029

中图分类号：

R9 [药学];

学科分类号：

1007 ;

摘要：

Detailing the conformational equilibria between global and local minimum energy structures of anti-inflammatory alpha-arylpropionic acids directly in solution is of the utmost importance for a better understanding of the structure-activity relationships, hence providing valuable clues for rational structure-based drug design studies. Here the conformational preferences of the widely used pharmaceutical ibuprofen were investigated in solution by NMR spectroscopy in weakly ordering phases. A thorough theoretical treatment of the anisotropic interactions that are relevant for NMR spectra led to a conformational model characterized by six pairs of symmetry-related conformers, in particular four couples of gauche structures, with a total probability of 93%, and 2 couples of trans structures, counting for the remaining 7%.

引用

页码：113 / 121

页数：9

共 74 条

[1] SOME BIOLOGICAL PROPERTIES OF 2-(4-ISOBUTYLPHENYL)-PROPIONIC ACID [J].