A structural study of bisphosphonate metal complexes. Alkaline earth metal complexes of (dichloromethylene)bisphosphonic acid P,P′-diethyl ester

Kontturi, Mervi; Vuokila-Laine, Eija; Peräniemi, Sirpa; Pakkanen, Tuula T.; Vepsäläinen, Jouko; Ahlgrén, Markku

doi:10.1039/b201124g

Cited by 33 publications

(16 citation statements)

References 13 publications

(9 reference statements)

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“…There are relatively few metal complexes from the mono ester derivatives of clodronate, but they form 2D and 3D structures, where the ethyl [12a, 12b, 12d] and phenyl ester 12a derivatives of clodronate both chelate and bridge the metal atoms. The symmetrical diester derivatives of clodronate, in turn, both act in a chelating manner and bridge the metal atoms with ionic radii of 0.74–1.42 Å 19, forming monomeric 12c, dimeric 12f, tetrameric [12g, 12h] and polymeric 12 structures, some of which form 1D and 2D structures through hydrogen bonding.…”

Section: Resultsmentioning

confidence: 99%

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Synthesis and Antioxidant Evaluation of Some New 3‐Substituted Coumarins

Hamama

Berghot

Baz

et al. 2011

Archiv der Pharmazie

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3-Acetylcoumarin (1) was utilized as a key intermediate for the synthesis of 2-aminothiazole derivative 3 via bromination of 1 to afford acetylbromide 2 followed by treatment with thiourea or via Biginelli reaction of 1. Treatment of 3 with 5-chloro-3-methyl-1-phenyl-1H-pyrazole-4-carbaldehyde, 2-methyl-4H-benzo[d][1,3]oxazin-4-one, furo[3,4-b]pyrazine-5,7-dione or 2-methyl-5,6,7,8-tetrahydro-4H-benzothieno[2,3-d][1,3]oxazin-4-one afforded diazine derivatives 4-7. Also, pyridopyrimidine 8 was obtained via a one pot reaction of 6-aminothiouracil, p-chlorobenzaldehyde and 3-acetylcoumarin. Moreover, refluxing of 6-aminothiouracil with one equivalent amount of 2 afforded the thiazolopyrimidine 9, while the pyrrolothiazolopyrimidine 10 was revealed when two equivalent amounts of 2 was used. Furthermore, treatment of enamine 11 with 2-aminobenzothiazole or 6-aminothiouracil afforded the pyrimidine derivatives 12 and 13, respectively. Transamination of enamine 11 with m-anisidine followed by cyclization of the resulting enaminone 14 gave the desired quinoline 15. Also, treatment of 11 with thiophenol in dioxane gave the mercapto derivative 16. Moreover, coupling of 11 with 4,6-dimethyl-1H-pyrazolo[3,4-b]pyridin-3-yl-diazonium chloride, followed by complete cyclization of the resulting product afforded the pyridopyrazolothiazine 19 via the intermediate 18. Furthermore, the pyrazolopyrimidine 20 was revealed via a one pot condensation of 11, 3-methyl-1-phenyl-1H-pyrazol-5(4H)-one and ammonium acetate. The thiadiazine derivatives 21-23 were obtained via treatment of 2 with the corresponding o-aminothiols. Desulphonation of 23 afforded the pyrazolotriazine 24. Finally, reaction of 2 with 2-hydroxybenzaldehyde gave benzofuran derivative 25. Representative compounds of the synthesized products were evaluated as antioxidant agents.

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Section: Resultsmentioning

confidence: 99%

“…All metal complexes of the L2 ligand form 2D structures through the hydrogen bonding of crystal water and coordinated water. In addition, the other diester derivatives, where the ester group is smaller, form also 1D structures through hydrogen bonding 12f.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Antioxidant Evaluation of Some New 3‐Substituted Coumarins

Hamama

Berghot

Baz

et al. 2011

Archiv der Pharmazie

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“…[14] However, we have reported structures of alkaline earth metal complexes of a symmetrical diethyl ester derivative of clodronic acid in which one O atom of each of the two phosphonate groups is masked by an ethyl group, and the results showed that this ligand provides 3Ϫ5 donor O atoms, producing dimeric and polymeric structures. [15] In the present study, three new polymeric structures of the calcium complex of clodronic acid, [{Ca 2 …”

Section: Introductionmentioning

confidence: 99%

A Structural Study of Bisphosphonate Metal Complexes − Three New Polymeric Structures of the Calcium Complex of Clodronic Acid

et al. 2004

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Three novel calcium complexes of clodronic acid were prepared and their structures determined by single‐crystal X‐ray diffractometry. Previously, a monomeric structure, [Ca{Cl2C(PO3H)2}(H2O)5] (1), has been determined, but the new structures are polymeric: [{Ca2[Cl2C(PO3)2](H2O)6}·4.5H2O]n (2), [{Ca2Na0.5[Cl2C(PO3)2](H2O)8}Cl0.5·4H2O]n (3) and [{Ca5[Cl2C(PO3)2]2(H2O)15}(NO3)2·1.5H2O]n (4); and they provide new, important information about the binding abilities of clodronic acid. Compounds 2−4 crystallise in the triclinic crystal system, the space group being P$\bar 1$ with Z = 2. Compound 2 consists of Ca atoms and Cl2MBP ligands connected to one‐dimensional chains. The chains are held together by hydrogen bonds formed by aqua ligands and lattice water molecules. The structure of 3 consists of similar calcium clodronate chains forming two‐dimensional layers through additional, six‐coordinate Na atoms. Compound 4 consists of two‐dimensional calcium clodronate layers, the calcium atoms are connected by Cl2MBP− and aqua ligands. The nitrate groups and lattice water molecules lie between the layers and hold them together. The layered compounds 3 and 4 reveal substantial porosity. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)

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“…The formation of such extended M-O-M structures was also observed with flexible as well as rigid phosphonic acids in barium phosphonates. Thus, the barium hydrogenphosphonates, Ba(HO 3 PC 6 H 5 ) 2 [24], Ba(HO 3 [28] or blocking one of the phosphonate oxygen atoms through the use of a phosphonic acid ester [29]. …”

Section: H(o 3 P-c 2 H 4 -So 3 ) 2à Ions Through Eight P/s-o-ba Bondsmentioning

confidence: 99%

Synthesis and characterization of 2-phosphonoethanesulfonic acid and a barium-hydrogenphosphonatoethanesulfonate — BaH(O3P–C2H4–SO3)

Sonnauer

Stock

2008

Journal of Solid State Chemistry

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A structural study of bisphosphonate metal complexes. Alkaline earth metal complexes of (dichloromethylene)bisphosphonic acid P,P′-diethyl ester

Cited by 33 publications

References 13 publications

Synthesis and Antioxidant Evaluation of Some New 3‐Substituted Coumarins

Synthesis and Antioxidant Evaluation of Some New 3‐Substituted Coumarins

A Structural Study of Bisphosphonate Metal Complexes − Three New Polymeric Structures of the Calcium Complex of Clodronic Acid

Synthesis and characterization of 2-phosphonoethanesulfonic acid and a barium-hydrogenphosphonatoethanesulfonate — BaH(O3P–C2H4–SO3)

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