Abstract
The X-ray crystal structures of two crystalline forms of 5-(2,3,5-trichlorophenyl)-2,4-diaminopyrimidine, C10H7Cl3N4 (code name BW1003C87) (I) and (II), have been carried out at liquid nitrogen temperature. A detailed comparison of the two structures is given. Both are centrosymmetric, with structure (I) in the triclinic space group P\(\bar 1,\) unit cell a = 6.4870(10), b = 9.216(2), c = 12.016(2) Å, α = 75.78(3)°, β = 89.95(3)°, γ = 83.45(3)°, V = 691.5(2) Å3, Z = 2 and density (calculated) = 1.544 Mg/m3; and (II) in the monoclinic space group P21/c, unit cell a = 12.000(2), b = 7.518(2), c = 13.450(3) Å, β = 97.87(3)°, V = 1202.0(5) Å3, Z = 4, Density (calculated) = 1.600 Mg/m3. Structure (I) includes a solvated CH3OH in the lattice. Final R indices [I > 2sigma(I)] are R1 = 0.0427, wR2 = 0.1075 for (I) and R1 = 0.0487, wR2 = 0.1222 for (II). R indices (all data) are R1 = 0.0470, wR2 = 0.1118 for (I) and R1 = 0.0623, wR2 = 0.1299 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. Both lamotrigine and 5-(2,3,5-trichlorophenyl)-2,4-diaminopyrimidine (code name BW1003C87), the subject of the present study, are anticonvulsant as well as neuroprotective in models of brain ischaemia and in a model of white matter ischaemia. BW1003C87 is a sodium channel blocker which also reduces the release of the neurotransmitter glutamate. The three dimensional structures reported here form part of a newly developed data base for the detailed investigation of members of this drug family and their biological activities.
Index Abstract
Rex A. Palmer, Brian S. Potter, Michael J Leach and Babur Z. Chowdhry
5-(2,3,5-trichlorophenyl)-2,4-diaminopyrimidine occurs in two crystalline forms whose X-ray structures are described here. The molecular conformations in (I) and (II) are quite distinct as illustrated, the ring linkage torsion angle differing by 23.5 deg. (I) has a methanol solvate molecule in the lattice.
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Acknowledgments
We thank Dr P. Barraclough (University of Greenwich) for the synthesis and provision of samples of BW1003C87. Low temperature X-ray intensity data were collected on the EPSRC single crystal X-ray data facility at Southampton University.
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Palmer, R.A., Potter, B.S., Leach, M.J. et al. Low Temperature X-ray Structures of Two Crystalline Forms (I) and (II) of the Pyrimidine Derivative and Sodium Channel Blocker BW1003C87: 5-(2,3,5-Trichlorophenyl)-2,4-diaminopyrimidine. J Chem Crystallogr 38, 407–411 (2008). https://doi.org/10.1007/s10870-008-9319-9
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DOI: https://doi.org/10.1007/s10870-008-9319-9