Palmer, Rex A., Potter, Brian S., Helliwell, Madeleine, Leach, Michael J. ORCID: 0000-0002-9859-1325 and Chowdhry, Babur Z. (2008) Central nervous system drugs: Low temperature X-ray structures of (I) the base 5-(2,3-dichlorophenyl)-2,4-diamino-6-fluoromethyl-pyrimidine (4030W92) and (II) 5-(2,6-dichlorophenyl)-1-H-2,4-diamino-6-methyl-pyrimidine methanesulphonic acid salt (227C89). Journal of Chemical Crystallography, 39 (1). pp. 36-41. ISSN 1074-1542 (Print), 1572-8854 (Online) (doi:https://doi.org/10.1007/s10870-008-9428-5)

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Abstract

The X-ray crystal structures of (I), the base 4030W92, 5-(2,3-dichlorophenyl)-2,4-diamino-6-fluoromethyl-pyrimidine, C11H9Cl2FN4, and (II) 227C89, the methanesulphonic acid salt of 5-(2,6-dichlorophenyl)-1-H-2,4-diamino-6-methyl-pyrimidine, C11H11Cl2N4 center dot CH3O3S, have been carried out at low temperature. A detailed comparison of the two structures is given. Structure (I) is non-centrosymmetric, crystallizing in space group P2(1) with unit cell a = 10.821(3), b = 8.290(3), c = 13.819(4) angstrom, beta = 105.980(6)degrees, V = 1191.8(6) angstrom(3), Z = 4 (two molecules per asymmetric unit) and density (calculated) = 1.600 mg/m(3). Structure (II) crystallizes in the triclinic space group P (1) over bar with unit cell a = 7.686(2), b = 8.233(2), c = 12.234(2) angstrom, alpha = 78.379(4), beta = 87.195(4), gamma = 86.811(4)degrees, V = 756.6(2) angstrom(3), Z = 2, density (calculated) = 1.603 mg/m(3). Final R indices [I > 2sigma(I)] are R1 = 0.0572, wR2 = 0.1003 for (I) and R1 = 0.0558, wR2 = 0.0982 for (II). R indices (all data) are R1 = 0.0983, wR2 = 0.1116 for (I) and R1 = 0.1009, wR2 = 0.1117 for (II). 5- Phenyl-2,4 diaminopyrimidine and 6-phenyl-1,2,4 triazine derivatives, which include lamotrigine (3,5-diamino-6-(2,3-dichlorophenyl)-1,2,4-triazine), have been investigated for some time for their effects on the central nervous system. The three dimensional structures reported here form part of a newly developed data base for the detailed investigation of members of this structural series and their biological activities.

Item Type:	Article
Additional Information:	[1] First published online: 19 June 2008. [2] First published in print: January 2009. [3] Journal of Chemical Crystallography, (2009), Volume 39, Issue 1, pp. 36-41.
Uncontrolled Keywords:	central nervous system drugs, pyrimidines, lamotrigines, lamotrigine, voltage-gated Na+ channel blockers, gated sodium channels, crystal structures and drug design
Subjects:	Q Science > QD Chemistry R Medicine > RM Therapeutics. Pharmacology
Pre-2014 Departments:	School of Science
Related URLs:	Publisher Organisation
Last Modified:	21 Oct 2020 14:37
URI:	http://gala.gre.ac.uk/id/eprint/1595

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