title: Synthesis, solution, and structural characterization of tetrahydrofuranyl-2,2-bisphosphonic acid disodium salt.
abstract: Bisphosphonates are biologically relevant therapeutics for bone disorders and cancer. Reaction of gamma-chlorobutyric acid, phosphorus acid, and phosphorus trichloride without the use of solvent gave the tetrahydrofuranyl-2,2-bisphosphonate sodium salt (Na(2)H(2)L). The Na(2)H(2)L was isolated, characterized in solution by (1)H, (13)C, and (31)P NMR spectroscopy and in solid state by single X-Ray crystallography. The crystal structure showed that the Na(2)H(2)L forms in the crystal infinite two-dimensional sheets stacked one parallel to the other. A comparison of the chelating properties of H(2)L(2-) with similar hydroxyl bisphosphonate ligands shows that the strength of the Na-O(furanyl/hydroxyl) bond is directly related to the total charge of the ligand anion.
authors.affiliation: Department of Chemistry, University of Cyprus, 1678 Nicosia, Cyprus.
authors.forename: Elena
authors.initials: E
authors.lastname: Maltezou
authors.forename: Marios
authors.initials: M
authors.lastname: Stylianou
authors.forename: Sudeshna
authors.initials: S
authors.lastname: Roy
authors.forename: Chryssoula
authors.initials: C
authors.lastname: Drouza
authors.forename: Anastasios D
authors.initials: AD
authors.lastname: Keramidas
references.citation: J Clin Oncol. 1998 Dec;16(12):3890-9
references.pmid: 9850035
references.citation: Acta Crystallogr C. 2000 Jun;56(Pt 6):720-2
references.pmid: 10902035
references.citation: Bone. 2006 May;38(5):617-27
references.pmid: 16046206
references.citation: J Am Chem Soc. 2009 Jun 24;131(24):8374-5
references.pmid: 19489581
references.citation: J Am Chem Soc. 2009 Apr 15;131(14):5153-62
references.pmid: 19309137
references.citation: Eur Spine J. 2003 Oct;12 Suppl 2:S142-6
references.pmid: 13680318
references.citation: Acta Crystallogr C. 2002 Oct;58(Pt 10):m494-7
references.pmid: 12359924
references.citation: Acta Crystallogr C. 2003 Dec;59(Pt 12):m543-5
references.pmid: 14671354
references.citation: Bone. 1999 Jul;25(1):97-106
references.pmid: 10423031
references.citation: Endocr Rev. 1998 Feb;19(1):80-100
references.pmid: 9494781
references.citation: Acta Crystallogr C. 2002 Feb;58(Pt 2):m77-80
references.pmid: 11828086
references.citation: Bone. 2007 Oct;41(4):668-78
references.pmid: 17644459