Structural study of metal complexes of bisphosphonate amide ester: copper, magnesium, zinc and cadmium complexes of (dichloromethylene)bisphosphonic acid P-piperidinium-P′-methyl ester

Jokiniemi, Jorma; Vuokila-Laine, Eija; Peräniemi, Sirpa; Vepsäläinen, Jouko; Ahlgrén, Markku

doi:10.1039/b616077h

Cited by 25 publications

(4 citation statements)

References 40 publications

(25 reference statements)

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“…Compound 1 is isostructural with the previously published nickel and zinc complexes of clodronic acid 16, and the M –O bond lengths and the O– M –O angles follow the same pattern. In addition, a similar bischelating bonding mode is found, for example, in the cobalt and vanadium complexes of medronate [8f, 15], copper complexes of etidronate [8c–8d], aluminium complexes of ethylenediphosphonate 16, magnesium complexes of clodronate 3a and calcium 12a and cadmium 12b complexes of monoethyl, and cobalt complexes of P‐piperidinium‐P′‐methyl 12c derivatives of clodronate.…”

Section: Resultsmentioning

confidence: 85%

“…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: 85%

Section: Resultsmentioning

confidence: 99%

Synthesis and Antioxidant Evaluation of Some New 3‐Substituted Coumarins

Hamama

Berghot

Baz

et al. 2011

Archiv der Pharmazie

View full text Add to dashboard Cite

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“…The minor or lack of P2Y 6 -R agonist and antagonist activity of 10 and 7, containing a bridging CCl 2 group (vs. 11 and 9, Fig. 5) may be related to the large size of dichloro methylene bisphosphonate, vs. difluoro methylene bisphosphonate or methylene bisphosphonate anion, 50 which may not be compatible with the binding pocket of the receptor. Reduced activation of P2Y 6 -R by 2'-dUDP analogues has been described before.…”

Section: Discussionmentioning

confidence: 98%

Synthesis and structure–activity relationship of uracil nucleotide derivatives towards the identification of human P2Y 6 receptor antagonists

Meltzer

Ethan

Arguin

et al. 2015

Bioorganic & Medicinal Chemistry

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“…Due to the selective inhibitory ability of N-BPs on the isoprenoid and cholesterol biosynthesis, extensive studies of BPs have been carried out to unveil their potential applications to other diseases related to Alzheimer's, immunomodulator and parasitological infections [13][14][15][16]. BPs are also known to own special metal-binding properties, [17] which has made great interests to scientists to explore the chemistry and metal conjugations of this category of compounds, [18,19] in particular for the development in nuclear medicines ( 186 Re therapy) [20] and radiopharmaceuticals ( 99 Tc imaging), [21][22][23] in advance material discoveries for bone and dental implants [24][25][26] as well as in nanotechnologies [27][28][29].…”

Section: Introductionmentioning

confidence: 99%

Biological evaluations of novel 2,3,3-Trisphosphonate in osteoclastic and osteoblastic activities

Cheong¹,

Huang²,

Detsch³

et al. 2017

Gen Med Open

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Bisphosphonates (BPs) are the first line treatment for many bone diseases including hypercalcimia associated with bone malignancies. In this paper, we introduce a new analogue of bisphosphonate called the 2,3,3-Trisphosphonate (2,3,3-TriPP) that was synthesised in a two steps reaction. In vitro investigations using a medically known bisphosphonate (Etidronate) and the 2,3,3-TrisPP were performed with an aim to evaluate biological effect of this novel compound in major bone cells. 2,3,3-TrisPP showed to have potential to supress the bone resorption process, as our data found that this novel compound exhibited cytotoxic effect in osteoclastic cells at a low concentration of 0.172 mg/mL (LC 50 ). A molecular docking computational simulation calculated a high level of binding affinity between the human farnesyl pyrophosphate synthase (hFPPS) and 2,3,3-TrisPP. This calculation suggested 2,3,3TrisPP may have undergone the mevalonate pathway to prevent the prenylation step during biosynthesis and subsequently resulted in the deactivation of osteoclastic cells. Finally, high levels of osteoblast mineralisation potentials were recorded upon treatments with 2,3,3-TrisPP (0.01-0.1 mg/ml), which implied 2,3,3-TrsiPP may also facilitate bone regeneration.

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Structural study of metal complexes of bisphosphonate amide ester: copper, magnesium, zinc and cadmium complexes of (dichloromethylene)bisphosphonic acid P-piperidinium-P′-methyl ester

Cited by 25 publications

References 40 publications

Synthesis and Antioxidant Evaluation of Some New 3‐Substituted Coumarins

Synthesis and Antioxidant Evaluation of Some New 3‐Substituted Coumarins

Synthesis and structure–activity relationship of uracil nucleotide derivatives towards the identification of human P2Y 6 receptor antagonists

Biological evaluations of novel 2,3,3-Trisphosphonate in osteoclastic and osteoblastic activities

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