NDLI: 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

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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

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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

Content Provider	Springer Nature Link
Author	Palmer, Rex A. Potter, Brian S. Leach, Michael J. Chowdhry, Babur Z.
Copyright Year	2008
Abstract	The X-ray crystal structures of two crystalline forms of 5-(2,3,5-trichlorophenyl)-2,4-diaminopyrimidine, C$_{10}$H$_{7}$Cl$_{3}$N$_{4}$ (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) Å$^{3}$, Z = 2 and density (calculated) = 1.544 Mg/m3; and (II) in the monoclinic space group P2$_{1}$/c, unit cell a = 12.000(2), b = 7.518(2), c = 13.450(3) Å, β = 97.87(3)°, V = 1202.0(5) Å$^{3}$, Z = 4, Density (calculated) = 1.600 Mg/m3. Structure (I) includes a solvated CH$_{3}$OH 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.Rex A. Palmer, Brian S. Potter, Michael J Leach and Babur Z. Chowdhry5-(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.
Starting Page	407
Ending Page	411
Page Count	5
File Format	PDF
ISSN	10741542
Journal	Journal of Chemical Crystallography
Volume Number	38
Issue Number	6
e-ISSN	15728854
Language	English
Publisher	Springer US
Publisher Date	2008-02-01
Publisher Place	Boston
Access Restriction	One Nation One Subscription (ONOS)
Subject Keyword	Central nervous system drugs Pyrimidines Lamotrigines Voltage gated Na$^{+}$ channel inhibitors Crystal structures and drug design Inorganic Chemistry Physical Chemistry Crystallography Organometallic Chemistry
Content Type	Text
Resource Type	Article
Subject	Chemistry Condensed Matter Physics

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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

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