NDLI: Low Temperature X-ray Crystallographic Structures of Two Lamotrigine Analogues: (I) 2-Methyl,3-amino, 5-imino-6-(2,3-dichlorophenyl)-1,2,4-triazine Water Solvate and (II) 2-Methyl,3,5-diamino-6-(2,3-dichlorophenyl)-1,2,4-triazine Isethionate, Hemi-hydrate

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Low Temperature X-ray Crystallographic Structures of Two Lamotrigine Analogues: (I) 2-Methyl,3-amino, 5-imino-6-(2,3-dichlorophenyl)-1,2,4-triazine Water Solvate and (II) 2-Methyl,3,5-diamino-6-(2,3-dichlorophenyl)-1,2,4-triazine Isethionate, Hemi-hydrate

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Low Temperature X-ray Crystallographic Structures of Two Lamotrigine Analogues: (I) 2-Methyl,3-amino, 5-imino-6-(2,3-dichlorophenyl)-1,2,4-triazine Water Solvate and (II) 2-Methyl,3,5-diamino-6-(2,3-dichlorophenyl)-1,2,4-triazine Isethionate, Hemi-hydrate

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 lamotrigine derivatives (I) 2-methyl, 3-amino, 5-imino-6-(2, 3-dichlorophenyl)-1,2,4-triazine, C$_{10}$H$_{9}$Cl$_{2}$N$_{5}$, as the hemi hydrate and (II) 2-methyl,3,5-diamino-6-(2,3-dichlorophenyl)-1,2,4-triazine, C$_{10}$H$_{10}$Cl$_{2}$N$_{5}$, as the isethionate-water solvate, have been carried out at liquid nitrogen temperature. A detailed comparison of the two structures is given. Both are monoclinic and centrosymmetric, with (I) in space group C2/c, and (II) in space group P2$_{1}$/n. For (I) the unit cell dimensions are a = 19.5466(10), b = 7.5483(4), c = 15.7861(8) Å, β = 91.458(3)°, volume = 2328.4(2) Å$^{3}$, Z = 8, density = 1.590 Mg/m$^{3}$; for (II). For (II) the unit cell dimensions are a = 6.0566(2), b = 11.0084(4) c = 23.9973(9) Å, β = 92.587(3)°, volume = 1598.35(10) Å$^{3}$, Z = 4, density = 1.597 Mg/m$^{3}$. For (I) final R indices [I > 2sigma(I)] are R1 = 0.0356, wR2 = 0.0782 and R indices (all data) are R1 = 0.0424, wR2 = 0.0817. For (II) final R indices [I > 2sigma(I)] are R1 = 0.0380, wR2 = 0.0871 and R indices (all data) R1 = 0.0558, wR2 = 0.0949. Both structures have a molecule of water of crystallization and (II) also includes a solvated CH$_{3}$SO$_{3}$. Comparisons are made between the two structures. Structure (I) is very unusual in having a = NH group at position C5′ on the triazine ring. No other examples of this particular substitution, which is usually −NH$_{2}$, have been reported.Rex A. Palmer, Brian S. Potter, Michael J Leach and Babur Z. ChowdhryThe crystal structures of (I) 2-methyl,3-amino, 5-imino-6-(2, 3-dichlorophenyl)-1, 2, 4-triazine, water solvate and (II) 2-methyl,3, 5-diamino-6-(2, 3-dichlorophenyl)-1, 2, 4-triazine isethionate water solvate are presented. The relative orientation of the two rings is shown to vary. Lamotrigine and analogues have been investigated for some time for their effects on the central nervous system. For example both lamotrigine and 5-(2,3,5-trichlorophenyl)-2,4-diaminopyrimidine (code name BW 1003C87) are voltage-gated sodium channel blockers as well as blocking the release of the neurotransmitter glutamate [D. R. Riddall, M. J. Leach, J. Garthwaite, Mol. Pharmacol. 2006, 69 (1), 278.3], BW10003C87 (like lamotrigine) has been shown to exhibit excitatory amino acid antagonist activity similar to that of three conventional antiepileptic drugs phenytoin, carbamazepine and phenobarbital [R. Lingamaneni, H. C. Hemmings Jr., Epilepsy Res. 1993, 15, 101.]. BW 1003C87 has also been shown [B. S. Meldrum, J. H. Swan, M. J. Leach, M. H. Millan, R. Gwinn, K. Kadota, S. H Graham, J. Chen, R. P. Simon , Brain Res., 1992, 593, 1.] to reduce the release of glutamate evoked by veratrine in brain tissue, providing a therapeutic approach in both cerebral ischemia and epilepsy. This is one of a series of papers on the structures of lamotrigine analogues.
Starting Page	255
Ending Page	260
Page Count	6
File Format	PDF
ISSN	10741542
Journal	Journal of Chemical Crystallography
Volume Number	38
Issue Number	4
e-ISSN	15728854
Language	English
Publisher	Springer US
Publisher Date	2008-01-30
Publisher Place	Boston
Access Restriction	One Nation One Subscription (ONOS)
Subject Keyword	Central nervous system drugs Triazines 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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X-ray Crystallographic Structures of Two Lamotrigine Analogues: (I) 3,5-Diamino-6-(2-chlorophenyl)-1,2,4-triazine Water Solvate and (II) 3,5-Diamino-6-(3,6-dichlorophenyl)-1,2,4-triazine Methanol Solvate

Structure of 3,5-diamino-6-(2,3-dichlorophenyl)-1,2,4-triazine isethionate solvate (lamotrigine isethionate)

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)

A new approach to the synthesis of lamotrigine and other 3,5-diamino-1,2,4-triazine derivatives

Synthesis of 2-methyl-1,2,4-triazolo[4,3-d]-1,2,4-triazino[2,3-a]-benzimidazole and 2-methyl-9-phenylimidazo[1,2-b]-1,2,4-triazolo[4,3-d]-1,2,4-triazine

Solubility of 5-(2-Chlorophenyl)-7-nitro-1,3-dihydro-1,4-benzodiazepin-2-one, 7-Chloro-1-methyl-5-phenyl-3H-1,4-benzodiazepin-2-one, and 6-(2,3-Dichlorophenyl)-1,2,4-triazine-3,5-diamine in the Mixtures of Poly(ethylene glycol) 600, Ethanol, and Water at a Temperature of 298.2 K

Synthesis and properties of substituted 3,5-bis(3-imino-2,3-dihydro-1H-isoindol-1-ylideneamino)-1,2,4-thiadiazoles

2,4-Diamino-6-methyl-1,3,5-triazine ethanol solvate

2,4-Diamino-6-methyl-1,3,5-triazine methanol solvate

Low Temperature X-ray Crystallographic Structures of Two Lamotrigine Analogues: (I) 2-Methyl,3-amino, 5-imino-6-(2,3-dichlorophenyl)-1,2,4-triazine Water Solvate and (II) 2-Methyl,3,5-diamino-6-(2,3-dichlorophenyl)-1,2,4-triazine Isethionate, Hemi-hydrate

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