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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...
Autores principales: | , , , |
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Formato: | Texto |
Lenguaje: | English |
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International Union of Crystallography
2008
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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. |
format | Text |
id | pubmed-2959469 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2008 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
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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