Citation: GUO Dong, SONG Jia-Xi, LI Dan, CHEN Jia-Mei, LIN Li-Rong, LU Tong-Bu, ZHANG Hui. Determination and Correlation of the Absolute Configurations of Chiral Nimodipine[J]. Acta Physico-Chimica Sinica, ;2016, 32(9): 2241-2254. doi: 10.3866/PKU.WHXB201606132 shu

Determination and Correlation of the Absolute Configurations of Chiral Nimodipine

GUO Dong ^1, ,
SONG Jia-Xi ² ,
LI Dan ¹ ,
CHEN Jia-Mei ² ,
LIN Li-Rong ¹ ,
LU Tong-Bu ² ,
ZHANG Hui ¹

1.
Department of Chemistry, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, Fujian Province, P. R. China;
2.
School of Chemistry and Chemical Engineering, Sun Yat-Sen University, Guangzhou 510275, P. R. China

Received Date: 12 May 2016
Revised Date: 13 June 2016

Fund Project: The project was supported by the National Natural Science Foundation of China (21273175, 21331007, 21271150) and Natural Science Foundation of Guangdong Province, China (S2012030006240).

The stereochemical structures and absolute configuration-pharmacological activity relationship of chiral l,4-dihydropyridines (1,4-DHPs) calcium channel drugs were summarized. Additionally, the polymorphic forms of nimodipine were investigated. The absolute configurations of a pair of chiral nimodipines as a conglomerate prepared by spontaneous resolution under chiral crystallization were confirmed via X- ray crystallographic analysis directly correlated with their solid-state and solution electronic circular dichroism (ECD) spectra. The solid-state and solution ECD spectra of chiral l,4-DHPs were obtained for the first time. This comprehensive method can be used to determine the absolute configurations of small organic molecules. Furthermore, it can be extended to correlate the absolute configurations of other series of chiral l,4-DHP derivatives in the future. We also presented some effective techniques to distinguish polymorphs of chiral active pharmaceutical ingredients (APIs), which differ from the non-chiral conventional methods, to allow qualitative identification of different chiral crystalline states of APIs in pharmaceutical preparations.
- 1,4-Dihydropyridine,
- Absolute configuration correlation,
- Nimodipine,
- Polymorphism,
- Active pharmaceutical ingredient,
- Spontaneous resolution,
- Electronic circular dichroism
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