Journal Title
Title of Journal: J Chem Crystallogr
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Abbravation: Journal of Chemical Crystallography
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Authors: Anna K Przybył Maciej Kubicki
Publish Date: 2012/03/03
Volume: 42, Issue: 7, Pages: 685-690
Abstract
The crystal structures of three 3halogeno derivatives of 13Nsubstituted cytisine have been determined by Xray diffraction The two 13acetyl substituted compounds 3bromo 1 and 3iodo 2 are isostructural with the isostructurality index as high as 99 They both crystallize in monoclinic P21 space group with unit cell parameters of a = 8470910 Å b = 9226612 Å c = 8605110 Å β = 9852811º 1 and a = 823226 Å b = 917247 Å c = 854946 Å β = 981817º 2 In turn 3bromo13tbutylcarbonate derivative 3 crystallizes in orthorhombic P212121 space group with a = 681713 Å b = 789944 Å c = 31465715 Å Conformation of the cytisine skeleton is similar in all three molecules with almost planar A ring sofa conformation of Bring and C ring being an almost ideal chair However the orientations of the double C=O bonds in 13Nsubstituents are completely different in 1 and 2 it is cis with respect to C12 C12N13C14O15 torsion angle is 334º in 1 and 136º in 2 while in 3 it is trans −17543º In the structures of 1 and 2 the driving force of the crystal architecture are quite strong C–H···X halogen bonds with C···X distances far shorter than the sums of van der Waals radii C···Br in 1 is 2943019 Å and C···I in 2 29743 In contrast in 3–partially as the consequence of different orientation of the substituent—there are no halogen bondings but instead some weak C–H···O contacts organize the molecules into twodimensional patternsFor many years cytisine has been used for smoking cessation in central and eastern European countries 2 3 It is a partial agonist at the α4β2 nAChR Cytisine also shows high affinity for other nAChR subtypes but the therapeutic consequence of them is unknown These receptors have been identified as promising targets for the treatment of several neurological disorders such as Parkinson’s and Alzheimer’s diseases Tourette’s syndrome dyskinesias schizophrenia anxiety attention deficit disorder and pain 4 5 6 Additionally this natural compound was found to decrease nicotineinduced extra cellular dopamine release in the nucleus accumbens 7 and was shown to reduce ethanol drinking behaviors in mice or rats 8 9 and ethanolinduced dopamine and its metabolite 10 Therefore nicotinic ligands could be developed as potential therapeutic candidates for bingelike ethanol drinking and dependence in humansRecent interest in the chemistry of cytisine 1 has been growing because of a lack of understanding as to the molecular basis of this underpinning partial agonist profile In terms of analogues manipulation of cytisine itself is readily achievable at C3 and C5 C10 and N12 11 12 13 14 15 16 17 18 19 20 but interest in cytisine as a target for total synthesis has also been significant as well as the synthesis of cytisine derivatives 21 22
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