Pyrimethaminium sulfosalicylate monohydrate

Hemamalini, Madhukar; Muthiah, Packianathan Thomas; Sridhar, Balasubramanian; Rajaram, R. Κ.

doi:10.1107/s1600536805012237

Cited by 18 publications

(19 citation statements)

References 8 publications

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“…The sulfonate O atoms mimic the role of the carboxylate group in generating the R 2 2 (8) ring motif (Bernstein et al, 1995;Etter, 1990). A similar type of interaction of the PMN cation with a sulfonate group has been reported (Hemamalini et al, 2005;Nirmalram & Thomas Muthiah, 2010). Base pairing via N4B-H4B1Á Á ÁN3A i and N4A-H4A1Á Á ÁN3B vi hydrogen bonds (see Scheme 4 and Table 13) generates a quadruple DADA array with the fused-ring motifs R 2 3 (8), R 2 2 (8) and R 3 3 (10) ( Fig.…”

Section: Table 13mentioning

confidence: 54%

Supramolecular hydrogen-bonding patterns in salts of the antifolate drugs trimethoprim and pyrimethamine

Darious

Muthiah

Perdih

2018

Acta Crystallogr C Struct Chem

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Nine salts of the antifolate drugs trimethoprim and pyrimethamine, namely, trimethoprimium [or 2,4-diamino-5-(3,4,5-trimethoxybenzyl)pyrimidin-1-ium] 2,5-dichlorothiophene-3-carboxylate monohydrate (TMPDCTPC, 1:1), CHNO·CHClOS, (I), trimethoprimium 3-bromothiophene-2-carboxylate monohydrate, (TMPBTPC, 1:1:1), CHNO·CHBrOS·HO, (II), trimethoprimium 3-chlorothiophene-2-carboxylate monohydrate (TMPCTPC, 1:1:1), CHNO·CHClOS·HO, (III), trimethoprimium 5-methylthiophene-2-carboxylate monohydrate (TMPMTPC, 1:1:1), CHNO·CHOS·HO, (IV), trimethoprimium anthracene-9-carboxylate sesquihydrate (TMPAC, 2:2:3), CHNO·CHO·1.5HO, (V), pyrimethaminium [or 2,4-diamino-5-(4-chlorophenyl)-6-ethylpyrimidin-1-ium] 2,5-dichlorothiophene-3-carboxylate (PMNDCTPC, 1:1), CHClN·CHClOS, (VI), pyrimethaminium 5-bromothiophene-2-carboxylate (PMNBTPC, 1:1), CHClN·CHBrOS, (VII), pyrimethaminium anthracene-9-carboxylate ethanol monosolvate monohydrate (PMNAC, 1:1:1:1), CHClN·CHO·CHOH·HO, (VIII), and bis(pyrimethaminium) naphthalene-1,5-disulfonate (PMNNSA, 2:1), 2CHClN·CHOS, (IX), have been prepared and characterized by single-crystal X-ray diffraction. In all the crystal structures, the pyrimidine N1 atom is protonated. In salts (I)-(III) and (VI)-(IX), the 2-aminopyrimidinium cation interacts with the corresponding anion via a pair of N-H...O hydrogen bonds, generating the robust R(8) supramolecular heterosynthon. In salt (IV), instead of forming the R(8) heterosynthon, the carboxylate group bridges two pyrimidinium cations via N-H...O hydrogen bonds. In salt (V), one of the carboxylate O atoms bridges the N1-H group and a 2-amino H atom of the pyrimidinium cation to form a smaller R(6) ring instead of the R(8) ring. In salt (IX), the sulfonate O atoms mimic the role of carboxylate O atoms in forming an R(8) ring motif. In salts (II)-(IX), the pyrimidinium cation forms base pairs via a pair of N-H...N hydrogen bonds, generating a ring motif [R(8) homosynthon]. Compounds (II) and (III) are isomorphous. The quadruple DDAA (D = hydrogen-bond donor and A = hydrogen-bond acceptor) array is observed in (I). In salts (II)-(IV) and (VI)-(IX), quadruple DADA arrays are present. In salts (VI) and (VII), both DADA and DDAA arrays co-exist. The crystal structures are further stabilized by π-π stacking interactions [in (I), (V) and (VII)-(IX)], C-H...π interactions [in (IV)-(V) and (VII)-(IX)], C-Br...π interactions [in (II)] and C-Cl...π interactions [in (I), (III) and (VI)]. Cl...O and Cl...Cl halogen-bond interactions are present in (I) and (VI), with distances and angles of 3.0020 (18) and 3.5159 (16) Å, and 165.56 (10) and 154.81 (11)°, respectively.

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Section: Table 13mentioning

confidence: 54%

Supramolecular hydrogen-bonding patterns in salts of the antifolate drugs trimethoprim and pyrimethamine

Darious

Muthiah

Perdih

2018

Acta Crystallogr C Struct Chem

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“…It selectively binds with DHFR enzyme through several hydrogen bonds (Hitchings & Burchall, 1965). The crystal structures of PMN (Sethuraman & Muthiah, 2002), PMN sulfosalicylate monohydrate (Hemamalini et al, 2005) and PMN benzoate complexes (Stanley et al, 2005) have been reported from our laboratory. The present study has been undertaken to study the hydrogen-bonding patterns in pyrimethaminium 3-chlorobenzoate (PMMB), (I).…”

Section: Commentmentioning

confidence: 93%

Hydrogen-bonding patterns in pyrimethaminium 3-chlorobenzoate

et al. 2006

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“…Table 5. ) and four other CSD entries [refcodes GAMFAC (Hemamalini et al, 2005), MUFMAB (Sethuraman & Thomas Muthiah, 2002), ULAXIO (Sethuraman et al, 2003) and VEVNIU (Devi, Muthiah, Bocelli & Cantoni, 2006)].…”

Section: Figurementioning

confidence: 99%

A new polymorph and two pseudopolymorphs of pyrimethamine

Tutughamiarso

Bolte

2011

Acta Crystallogr C

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Due to its donor-acceptor-donor site, the antimalarial drug pyrimethamine [systematic name: 5-(4-chlorophenyl)-6-ethylpyrimidine-2,4-diamine] is a potential component of a supramolecular synthon. During a cocrystallization screen, one new polymorph of solvent-free pyrimethamine, C(12)H(13)ClN(4), (I), and two pseudopolymorphs, pyrimethamine dimethyl sulfoxide monosolvate, C(12)H(13)ClN(4)·C(2)H(6)OS, (Ia), and pyrimethamine N-methylpyrrolidin-2-one monosolvate, C(12)H(13)ClN(4)·C(5)H(9)NO, (Ib), were obtained. In (I), (Ia), (Ib) and the previously reported polymorph, the pyrimethamine molecules exhibit similar conformations and form R(2)(2)(8) dimers stabilized by a pair of N-H···N hydrogen bonds. However, the packing arrangements are completely different. In (I), the dimers are connected by two additional N-H···N hydrogen bonds to form ribbons and further connected into a two-dimensional network parallel to (100), while layers containing N-H···Cl hydrogen-bonded pyrimethamine ribbons are observed in the packing of the known polymorph. In the two pseudopolymorphs, two pyrimethamine molecules are linked to form R(2)(2)(8) dimers and the solvent molecules are connected to the dimers by R(2)(3)(8) interactions involving two N-H···O hydrogen bonds. These arrangements are connected to form zigzag chains by N-H···Cl interactions in (Ia) and to form ribbons by N-H...N interactions in (Ib). Unexpectedly, a reaction between pyrimethamine and N-methylpyrrolidin-2-one occurred during another cocrystallization experiment from a solvent mixture of N-methylpyrrolidin-2-one and dimethyl sulfoxide, yielding solvent-free 5,5'-{[5-(4-chlorophenyl)-6-ethylpyrimidine-2,4-diyl]bis(azanediyl)}bis(1-methylpyrrolidin-2-one), C(22)H(27)ClN(6)O(2), (II). In the packing of (II), the pyrimethamine derivatives are N-H···O hydrogen bonded to form ribbons. A database study was carried out to compare the molecular conformations and hydrogen-bonding interactions of pyrimethamine.

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Pyrimethaminium sulfosalicylate monohydrate

Abstract: Key indicatorsSingle-crystal X-ray study T = 273 K Mean (C-C) = 0.004 Å R factor = 0.036 wR factor = 0.106 Data-to-parameter ratio = 12.9For details of how these key indicators were automatically derived from the article, see

Cited by 18 publications

References 8 publications

Supramolecular hydrogen-bonding patterns in salts of the antifolate drugs trimethoprim and pyrimethamine

Supramolecular hydrogen-bonding patterns in salts of the antifolate drugs trimethoprim and pyrimethamine

Hydrogen-bonding patterns in pyrimethaminium 3-chlorobenzoate

A new polymorph and two pseudopolymorphs of pyrimethamine

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