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Conformational analysis of ticagrelor: effect of noncovalent interaction on conformational population.

Authors :
Fan, Qiangwen
Tan, Hongbo
Wang, Yeming
Song, Xiuqing
Yan, Hong
Source :
Structural Chemistry. Dec2018, Vol. 29 Issue 6, p1663-1670. 8p.
Publication Year :
2018

Abstract

In order to track the source of duplicated peaks in the 1H-NMR spectrum of Ticagrelor, variable-temperature NMR (VT-NMR) experiment was carried out with temperature increasing from 300 to 343 K. The result showed that the phenomenon was brought forth by coexistence of conformational isomers. Subsequently, conformational search was carried out by molecular mechanics (MM) stimulations associating with quantum mechanics (QM) calculations. The results revealed that the isomers resulting in duplicated proton peaks were introduced by the rotation of 2,4-diflurophenyl group on C3’position of cyclopropyl. Finally, noncovalent interaction (NCI) topological analysis of the conformers exhibited that CH-π interactions and H-bonds play important roles in controlling the population of conformers of ticagrelor. [ABSTRACT FROM AUTHOR]

Details

Language :
English
ISSN :
10400400
Volume :
29
Issue :
6
Database :
Academic Search Index
Journal :
Structural Chemistry
Publication Type :
Academic Journal
Accession number :
132696429
Full Text :
https://doi.org/10.1007/s11224-018-1143-z