Effect of a minor component on thermal transformation of crystalline 6-mercaptopurine.

Nakamachi, Hideo; Wada, Yutaka; Aoki, Isamu; Kodama, Yoshihiko; Kuroda, Koji

doi:10.1248/cpb.29.2956

Cited by 5 publications

(6 citation statements)

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“…All the H atoms were positioned geometrically and refined using riding model approximation, with C−H = 0.86-0.93 Å and U iso (H) = 1.2 U eq (parent atom). The R-factor of the structure (2.48 %) confirms the convergence of the structure, which is better than the earlier report [30].…”

Section: Single Crystal Xrd Studiessupporting

confidence: 41%

“…The compound crystallized in the monoclinic crystal system with P2 1 /n space group and the determined unit cell parameters were matched with the already reported data. However, the present crystal structure has better R-factor (2.48 % instead of the previous 4.24 % and 4.40 %) than the earlier report [30]. The protonation on the cation is confirmed from the elongated C-N bond distances [1.35 (2) …”

Section: Molecular Geometrymentioning

confidence: 44%

“…The structural and solubility studies of co-crystals of 6MP with 4-hydroxybenzoic acid and 2,4-dihydroxybenzoic acid were already reported [27]. The crystal and molecular structure of anhydrous 6-mercaptopurine [28], 6-mercaptopurine monohydrate [29] and 6-mercaptopurine hydrochloride [30] were also reported. The present work is carried out as a re-determination of the crystal and molecular structure of chloride salt of 6MP in an elaborate narration about hydrogen bonding network and the intermolecular assembly with improved R-factor.…”

Section: A C C E P T E D Accepted Manuscriptmentioning

confidence: 99%

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Hydrogen bonding motifs, spectral characterization, theoretical computations and anticancer studies on chloride salt of 6-mercaptopurine: An assembly of corrugated lamina shows enhanced solubility

Kumar

Athimoolam

Sridhar

2015

Journal of Molecular Structure

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Section: Single Crystal Xrd Studiessupporting

confidence: 41%

Section: Molecular Geometrymentioning

confidence: 44%

Section: A C C E P T E D Accepted Manuscriptmentioning

confidence: 99%

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Hydrogen bonding motifs, spectral characterization, theoretical computations and anticancer studies on chloride salt of 6-mercaptopurine: An assembly of corrugated lamina shows enhanced solubility

Kumar

Athimoolam

Sridhar

2015

Journal of Molecular Structure

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“…9 6-Mercaptopurine is a biologically interesting ligand with a wide area of potential applications. 16,17 In metal complexes the ligand predominantely acts as chelate [via S and N(7), formula j] here or as monodentate thiolate. 18 The latter form has also been found in gold() compounds.…”

Section: Resultsmentioning

confidence: 99%

Reactions of dichloro[2-(dimethylaminomethyl)phenyl-C1,N ]gold(III), [Au(damp-C1,N )Cl2], with heterocyclic thiols. Evidence for Au–N bond cleavage and protonation of the dimethylamino group

Abram¹,

Mack²,

Ortner³

et al. 1998

J. Chem. Soc., Dalton Trans.

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Dichloro[2-(dimethylaminomethyl)phenyl-C 1 ,N]gold(), [Au(damp-C 1 ,N)Cl 2 ], reacts with 2-mercapto-1,3thiazoline (HSthiaz), 2-mercaptopyridine (HSpy), sodium 1-methylmercaptotetrazolate (NaSmetetraz), 4-methyl-3-mercapto-1,2,4-triazole (HSmetriaz) or 6-mercaptopurine (HSpur) under cleavage of the Au᎐N bond and protonation of the dimethylamino group. Compounds of general formulae [Au(Hdamp-C 1 )Cl(HL) 2 ] 2ϩ (HL = HSthiaz or HSpy), [Au(Hdamp-C 1 )Cl(L)] (L = Spur Ϫ ) or [Au(Hdamp-C 1 )(L) 3 ] (L = Smetetraz Ϫ ) have been isolated and characterized. The reaction with HSmetriaz leads to a rapid reduction of the metal and the formation of the gold() complex [Au(HSmetriaz) 2 ] ϩ . The crystal structures of [Au(Hdamp-C 1 )Cl(HSthiaz) 2 ]Cl 2 ؒMe 2 CO, [Au(Hdamp-C 1 )Cl(HSpy) 2 ]ؒH 2 O, [Au(Hdamp-C 1 )(Smetetraz) 3 ] and [Au(Hdamp-C 1 )Cl(Spur)]Cl have been elucidated showing the gold atoms in distorted square-planar co-ordination environments. Generally, one or more hydrogen atoms of the heterocyclic ligands and/or the NMe 2 H ϩ group form hydrogen bonds in the solid-state structures. The reaction of Na[AuCl 4 ] with Na(Smetetraz) and [NEt 4 ]Br yields bright red crystals of [NEt 4 ][Au(Smetetraz) 4 ], the first structurally characterized gold() complex with four monodentate thiolate ligands. The structure of the complex shows well separated [Au(Smetetraz) 4 ] Ϫ anions with Au᎐S distances of 2.354(4) Å. Square-planar gold() complexes containing 2-(dimethylaminomethyl)phenyl-C 1 ,N, (damp-C 1 ,N) Ϫ , have been known since 1984. 1 Key compounds are the dichloro and diacetato complexes [Au(damp-C 1 ,N)Cl 2 ] (1a) and [Au(damp-C 1 ,N )-(CH 3 CO 2 ) 2 ] 1 (1b) which recently have been studied by structural analysis 2 showing distorted square-planar co-ordination spheres for the gold atoms. During ligand exchange reactions the chloro or acetato ligands are preferably replaced. 2-9 Only a few examples are reported where the Au᎐N bond is cleaved. 9 However, to our knowledge, protonation of the liberated N(CH 3 ) 2 group has not yet been observed for gold compounds.

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“…Due to the complexity of solid-state reaction, the stability-indicating kinetic interpretation has been fully discussed in only a few reports (1,7,8). differential scanning calorimetry (4,5), and X-ray powder diffractometry (7,8). differential scanning calorimetry (4,5), and X-ray powder diffractometry (7,8).…”

mentioning

confidence: 99%

Kinetic Study of the Polymorphic Transformations of Phenylbutazone

Matsuda

Tatsumi

Chiba

et al. 1984

Journal of Pharmaceutical Sciences

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Effect of a minor component on thermal transformation of crystalline 6-mercaptopurine.

Cited by 5 publications

References 0 publications

Hydrogen bonding motifs, spectral characterization, theoretical computations and anticancer studies on chloride salt of 6-mercaptopurine: An assembly of corrugated lamina shows enhanced solubility

Hydrogen bonding motifs, spectral characterization, theoretical computations and anticancer studies on chloride salt of 6-mercaptopurine: An assembly of corrugated lamina shows enhanced solubility

Reactions of dichloro[2-(dimethylaminomethyl)phenyl-C1,N ]gold(III), [Au(damp-C1,N )Cl2], with heterocyclic thiols. Evidence for Au–N bond cleavage and protonation of the dimethylamino group

Kinetic Study of the Polymorphic Transformations of Phenylbutazone

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