55422-18-9Relevant articles and documents
Synthesis of new functionalized aryl and pyridyl aminomethylenebisphosphonic acids and their derivatives via silicon-assisted methodology
Prishchenko, Andrey A.,Alekseyev, Roman S.,Livantsov, Mikhail V.,Novikova, Olga P.,Livantsova, Ludmila I.,Petrosyan, Valery S.
, (2020)
The new convenient synthesis of functionalized aryl and pyridyl aminomethylenebisphosphonic acids and their derivatives has been developed via silicon-assisted methodology. New functionalized aminomethylenebisphosphonic acids containing pyridines moieties were obtained using unique reaction of tris(trimethylsilyl) phosphite with N-formyl aminopyridines and trimethylsilyl triflate as a catalyst under mild conditions. Intermediates – tetra(trimethylsilyl) aminomethylenebisphosphonates formed, were converted to the target acids by further treatment with methanol excess. In contrast the corresponding tetraethyl aminomethylenebisphosphonates were synthesized under heating (130 °C) of four component mixture (diethyl trimethylsilyl phosphite, triethyl orthoformate, aryl- or pyridylamine, and diethyl phosphite) in the presence of zinc chloride catalyst. The catalytic schemes of target substances formation are proposed and thoroughly discussed.
Microwave-assisted synthesis of (aminomethylene)bisphosphine oxides and (aminomethylene)bisphosphonates by a three-component condensation
Bálint, Erika,Tajti, ádám,Dzielak, Anna,H?gele, Gerhard,Keglevich, Gy?rgy
supporting information, p. 1493 - 1502 (2016/08/03)
A practical method was elaborated for the synthesis of (aminomethylene)bisphosphine oxides comprising the catalyst- and solventfree microwave-assisted three-component condensation of primary amines, triethyl orthoformate and two equivalents of diphenylpho
Bisphosphonic acids as effective inhibitors of Mycobacterium tuberculosis glutamine synthetase
Kosikowska, Paulina,Bochno, Marta,Macegoniuk, Katarzyna,Forlani, Giuseppe,Kafarski, Pawe?,Berlicki, ?ukasz
, p. 931 - 938 (2016/10/09)
Inhibition of glutamine synthetase (GS) is one of the most promising strategies for the discovery of novel drugs against tuberculosis. Forty-three bisphosphonic and bis-H-phosphinic acids of various scaffolds, bearing aromatic substituents, were screened
Arylamino methylene bisphosphonate derivatives as bone seeking matrix metalloproteinase inhibitors
Tauro, Marilena,Laghezza, Antonio,Loiodice, Fulvio,Agamennone, Mariangela,Campestre, Cristina,Tortorella, Paolo
, p. 6456 - 6465 (2013/10/22)
The complexity of matrix metalloproteinase inhibitors (MMPIs) design derives from the difficulty in carefully addressing their inhibitory activity towards the MMP isoforms involved in many pathological conditions. In particular, specific metalloproteinases, such as MMP-2 and MMP-9, are key regulators of the 'vicious cycle' occurring between tumor metastases growth and bone remodeling. In an attempt to devise new approaches to selective inhibitor derivatives, we describe novel bisphosphonate bone seeking MMP inhibitors (BP-MMPIs), capable to be selectively targeted and to overcome undesired side effects of broad spectrum MMPIs. In vitro activity (IC50 values) for each inhibitor was determined against MMP-2, -8, -9 and -14, because of their relevant role in skeletal development and renewal. The results show that BP-MMPIs reached IC50 values of enzymatic inhibition in the low micromolar range. Computational studies, used to rationalize some trends in the observed inhibitory profiles, suggest a possible differential binding mode in MMP-2 that explains the selective inhibition of this isoform. In addition, survival assay was conducted on J774 cell line, a well known model system used to evaluate the structure-activity relationship of BPs for inhibiting bone resorption. The resulting data, confirming the specific activity of BP-MMPIs, and their additional proved propensity to bind hydroxyapatite powder in vitro, suggest a potential use of BP-MMPIs in skeletal malignancies.
The preparation of N-substituted aminomethylidenebisphosphonates and their tetraalkyl esters via reaction of isonitriles with trialkyl phosphites and hydrogen chloride. Part 1
Goldeman, Waldemar,Kluczyński, Artur,Soroka, Miros?aw
, p. 5290 - 5292 (2012/11/13)
The reaction of isonitriles with trialkyl phosphites in the presence of hydrogen chloride gives tetraalkyl N-substituted aminomethylidenebisphosphonates via N-methylideneaminium (isonitrilium) salts. Hydrolysis or dealkylation of these tetraalkyl esters gives N-substituted aminomethylidenebisphosphonic acids in high yields.
Synthesis of the new types of N-substituted aminomethylenebisorganophosphorus acids and their derivatives
Prishchenko, Andrey A.,Livantsov, Mikhail V.,Novikova, Olga P.,Livantsova, Ludmila I.,Petrosyan, Valery S.
experimental part, p. 319 - 324 (2010/08/05)
The interaction of esters of trivalent organophosphorus acids containing PH and POSiMe3 fragments with various derivatives of formamide is proposed as convenient methods for the synthesis of new N-substituted aminomethylenebisorganophos-phorus acids and their derivatives with three-, four-, and five-coordinated phosphorus. Also the new functionalized derivatives of the new aminomethylenebisphosphinic acids with substituted hydroxymethyl moieties are synthesized, and some properties of the obtained compounds are presented.
A microwave-assisted solvent- and catalyst-free synthesis of aminomethylene bisphosphonates
Kaboudin, Babak,Alipour, Soheil
experimental part, p. 4243 - 4245 (2009/10/26)
A convenient preparative approach for the synthesis of aminomethylene bisphosphonates is developed which involves treatment of amines with triethyl orthoformate and diethyl phosphite under microwave irradiation.
Optimization, continuation and lack of the one-step diphosphorylation reaction. Assay of modification of the tetraethyl-(pyrrolidine-2,2-diyl)bisphosphonate
Olive, Gilles,Jacques, Alain
, p. 33 - 46 (2007/10/03)
The optimization of the one-step diphosphorylation reaction is reported. The synthesis of new α-aminobisphosphonates with four- and six-membered rings and acyclic species with several substituents on the nitrogen atom and on the carbon atom bearing the two phosphorus atoms is described.
