7-(5-Methyl­sulfanyl-β-d-erythrofuran­osyl)-7H-pyrrolo­[2,3-d]pyrimidin-4-amine monohydrate (MT-tubercidin·H(2)O)

The title compound, C(12)H(16)N(4)O(3)S·H(2)O, which has potential as a possible anti­malarial drug, was studied when small deviations in melting points, for two differently aged preparations, were observed. The unexpected existence of a water mol­ecule of crystallization is considered to be the cau...

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Detalles Bibliográficos
Autores principales: Gainsford, Graeme J., Fröhlich, Richard F. G., Evans, Gary B.
Formato: Texto
Lenguaje:English
Publicado: International Union of Crystallography 2010
Materias:
Organic Papers
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3006811/
https://www.ncbi.nlm.nih.gov/pubmed/21587912
http://dx.doi.org/10.1107/S1600536810020179
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author Gainsford, Graeme J.
Fröhlich, Richard F. G.
Evans, Gary B.
author_facet Gainsford, Graeme J.
Fröhlich, Richard F. G.
Evans, Gary B.
author_sort Gainsford, Graeme J.
collection PubMed
description The title compound, C(12)H(16)N(4)O(3)S·H(2)O, which has potential as a possible anti­malarial drug, was studied when small deviations in melting points, for two differently aged preparations, were observed. The unexpected existence of a water mol­ecule of crystallization is considered to be the cause of this variation. The 7H-pyrrolo­[2,3-d]pyrimidine unit is very slightly puckered with a total puckering amplitude of 0.035 (2) Å; its mean plane makes an angle of 88.40 (12)° with the mean plane through the ribofuranosyl unit. In the crystal, the mol­ecules are bound by strong O—H⋯N and N—H⋯O hydrogen bonds, utilizing all available protons and linking mainly through the water of crystallization.
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spelling pubmed-30068112010-12-30 7-(5-Methyl­sulfanyl-β-d-erythrofuran­osyl)-7H-pyrrolo­[2,3-d]pyrimidin-4-amine monohydrate (MT-tubercidin·H(2)O) Gainsford, Graeme J. Fröhlich, Richard F. G. Evans, Gary B. Acta Crystallogr Sect E Struct Rep Online Organic Papers The title compound, C(12)H(16)N(4)O(3)S·H(2)O, which has potential as a possible anti­malarial drug, was studied when small deviations in melting points, for two differently aged preparations, were observed. The unexpected existence of a water mol­ecule of crystallization is considered to be the cause of this variation. The 7H-pyrrolo­[2,3-d]pyrimidine unit is very slightly puckered with a total puckering amplitude of 0.035 (2) Å; its mean plane makes an angle of 88.40 (12)° with the mean plane through the ribofuranosyl unit. In the crystal, the mol­ecules are bound by strong O—H⋯N and N—H⋯O hydrogen bonds, utilizing all available protons and linking mainly through the water of crystallization. International Union of Crystallography 2010-06-18 /pmc/articles/PMC3006811/ /pubmed/21587912 http://dx.doi.org/10.1107/S1600536810020179 Text en © Gainsford et al. 2010 http://creativecommons.org/licenses/by/2.0/uk/ This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
spellingShingle Organic Papers
Gainsford, Graeme J.
Fröhlich, Richard F. G.
Evans, Gary B.
7-(5-Methyl­sulfanyl-β-d-erythrofuran­osyl)-7H-pyrrolo­[2,3-d]pyrimidin-4-amine monohydrate (MT-tubercidin·H(2)O)
title 7-(5-Methyl­sulfanyl-β-d-erythrofuran­osyl)-7H-pyrrolo­[2,3-d]pyrimidin-4-amine monohydrate (MT-tubercidin·H(2)O)
title_full 7-(5-Methyl­sulfanyl-β-d-erythrofuran­osyl)-7H-pyrrolo­[2,3-d]pyrimidin-4-amine monohydrate (MT-tubercidin·H(2)O)
title_fullStr 7-(5-Methyl­sulfanyl-β-d-erythrofuran­osyl)-7H-pyrrolo­[2,3-d]pyrimidin-4-amine monohydrate (MT-tubercidin·H(2)O)
title_full_unstemmed 7-(5-Methyl­sulfanyl-β-d-erythrofuran­osyl)-7H-pyrrolo­[2,3-d]pyrimidin-4-amine monohydrate (MT-tubercidin·H(2)O)
title_short 7-(5-Methyl­sulfanyl-β-d-erythrofuran­osyl)-7H-pyrrolo­[2,3-d]pyrimidin-4-amine monohydrate (MT-tubercidin·H(2)O)
title_sort 7-(5-methyl­sulfanyl-β-d-erythrofuran­osyl)-7h-pyrrolo­[2,3-d]pyrimidin-4-amine monohydrate (mt-tubercidin·h(2)o)
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3006811/
https://www.ncbi.nlm.nih.gov/pubmed/21587912
http://dx.doi.org/10.1107/S1600536810020179
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