Abstract
The high-resolution X-ray data for two bioactive molecules: cytisine (1) and its N-methyl derivative (2) have been collected up to sinθ/λ = 1.12 Å−1 for 1 and 1.0 Å−1 for 2. This data was used for modeling of the fine features of electron density distribution, including bonding density and electron lone pairs. The quality of the model was checked by, e.g., rigid bond test and RDA analysis. The topological analysis (gradient field analysis) has been also performed for both inter- and intramolecular interactions. In case of 1 a number of intermolecular interactions, from relatively strong N-H···O hydrogen bonds to weak H···H contacts was found, and their topological features were analyzed. For N-methyl derivative, only few intermolecular bonding contacts were found. The analyzed features show that besides the structural similarities of both alkaloids, the electron density distribution and consequently all its derivatives differ quite significantly in places.
Highlights
Cytisine is a quinolizidine alkaloid obtained from plants belonging to the Fabaceae (Leguminosae) family
Comparison of the structures of nicotine and cytisine (Scheme 1) showed that the quasi-aromatic ring in cytisine and the pyridine ring in nicotine are associated in a similar way with respect to the nitrogen atom in the bispidine ring system and in the pyrrolidine ring [8]
Cytisine shows an affinity towards the specific subunits of nicotine acetylcholine receptors, nAChRs
Summary
Cytisine is a quinolizidine alkaloid obtained from plants belonging to the Fabaceae (Leguminosae) family. We present the analysis of a charge density distribution and intermolecular interactions in the cytisine [(−)-1,2,3,4,5,6Hexahydro-1,5-methano-8H-pyrido(1,2-a)(1,5)diazocin-8one] (1) and N-methylcytisine [(−)-1,2,3,4,5,6-hexahydro-3methyl-1,5-methano-8H-pyrido(1,2-a)(1,5)diazocin-8-one] (2) crystals The results of these studies are supposed to provide high-quality electron density distribution data, which can be used in SAR studies and in docking studies of the active site if the appropriate receptor. Those two compounds, despite the relatively small changes in their structures, display quite significant differences in affinity towards α4β2 subtype of AChRs [12].
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