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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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Detalles Bibliográficos
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
Descripción
Sumario: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.