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Methyl [hydr­oxy(phen­yl)phosphono­meth­yl]phospho­nate methanol solvate

The title compound, C(8)H(12)O(7)P(2)·CH(4)O, is a monoesterified bis­phospho­nate (or 1-hydroxy­methyl­ene-1,1-bis­phospho­nic acid). These synthetic compounds are widely used in medicine to inhibit bone resorption in diseases like osteoporosis, and are characterized by a stable P—C—P group and are...

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Autores principales: Dupont, Nathalie, Retailleau, Pascal, Migianu-Griffoni, Evelyne, Barbey, Carole
Formato: Texto
Lenguaje:English
Publicado: International Union of Crystallography 2008
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2959469/
https://www.ncbi.nlm.nih.gov/pubmed/21201089
http://dx.doi.org/10.1107/S160053680802285X
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author Dupont, Nathalie
Retailleau, Pascal
Migianu-Griffoni, Evelyne
Barbey, Carole
author_facet Dupont, Nathalie
Retailleau, Pascal
Migianu-Griffoni, Evelyne
Barbey, Carole
author_sort Dupont, Nathalie
collection PubMed
description The title compound, C(8)H(12)O(7)P(2)·CH(4)O, is a monoesterified bis­phospho­nate (or 1-hydroxy­methyl­ene-1,1-bis­phospho­nic acid). These synthetic compounds are widely used in medicine to inhibit bone resorption in diseases like osteoporosis, and are characterized by a stable P—C—P group and are thus analogs of inorganic pyrophosphate. By masking one or several ionizable groups, introduced as phosphono­ester, it was anti­cipated the formation of prodrugs with higher lipophilicity that could facilitate the drug delivery and metabolization. Mol­ecules are paired by inter­molecular hydrogen bonds involving the phospho­nic groups. In addition, dimers are connected side-by-side, building infinite ribbons along the a-axis direction; these ribbons are cross-linked perpendicularly along the b-axis direction via a methanol solvent mol­ecule (disordered over two sites with occupancy factors ca 0.6 and 0.4), forming an extended inter­molecular hydrogen-bonded network. The H atoms of the methyl group in the main molecule are disordered equally over two positions.
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spelling pubmed-29594692010-12-30 Methyl [hydr­oxy(phen­yl)phosphono­meth­yl]phospho­nate methanol solvate Dupont, Nathalie Retailleau, Pascal Migianu-Griffoni, Evelyne Barbey, Carole Acta Crystallogr Sect E Struct Rep Online Organic Papers The title compound, C(8)H(12)O(7)P(2)·CH(4)O, is a monoesterified bis­phospho­nate (or 1-hydroxy­methyl­ene-1,1-bis­phospho­nic acid). These synthetic compounds are widely used in medicine to inhibit bone resorption in diseases like osteoporosis, and are characterized by a stable P—C—P group and are thus analogs of inorganic pyrophosphate. By masking one or several ionizable groups, introduced as phosphono­ester, it was anti­cipated the formation of prodrugs with higher lipophilicity that could facilitate the drug delivery and metabolization. Mol­ecules are paired by inter­molecular hydrogen bonds involving the phospho­nic groups. In addition, dimers are connected side-by-side, building infinite ribbons along the a-axis direction; these ribbons are cross-linked perpendicularly along the b-axis direction via a methanol solvent mol­ecule (disordered over two sites with occupancy factors ca 0.6 and 0.4), forming an extended inter­molecular hydrogen-bonded network. The H atoms of the methyl group in the main molecule are disordered equally over two positions. International Union of Crystallography 2008-09-06 /pmc/articles/PMC2959469/ /pubmed/21201089 http://dx.doi.org/10.1107/S160053680802285X Text en © Dupont et al. 2008 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
Dupont, Nathalie
Retailleau, Pascal
Migianu-Griffoni, Evelyne
Barbey, Carole
Methyl [hydr­oxy(phen­yl)phosphono­meth­yl]phospho­nate methanol solvate
title Methyl [hydr­oxy(phen­yl)phosphono­meth­yl]phospho­nate methanol solvate
title_full Methyl [hydr­oxy(phen­yl)phosphono­meth­yl]phospho­nate methanol solvate
title_fullStr Methyl [hydr­oxy(phen­yl)phosphono­meth­yl]phospho­nate methanol solvate
title_full_unstemmed Methyl [hydr­oxy(phen­yl)phosphono­meth­yl]phospho­nate methanol solvate
title_short Methyl [hydr­oxy(phen­yl)phosphono­meth­yl]phospho­nate methanol solvate
title_sort methyl [hydr­oxy(phen­yl)phosphono­meth­yl]phospho­nate methanol solvate
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2959469/
https://www.ncbi.nlm.nih.gov/pubmed/21201089
http://dx.doi.org/10.1107/S160053680802285X
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AT migianugriffonievelyne methylhydroxyphenylphosphonomethylphosphonatemethanolsolvate
AT barbeycarole methylhydroxyphenylphosphonomethylphosphonatemethanolsolvate