19928-97-3Relevant academic research and scientific papers
On the reaction of carbonyl diphosphonic acid with hydroxylamine and O-alkylhydroxylamines: Unexpected degradation of P-C-P bridge
Khomich, Olga A.,Yanvarev, Dmitry V.,Novikov, Roman A.,Kornev, Alexey B.,Puljulla, Elina,Veps?l?inen, Jouko,Khomutov, Alex R.,Kochetkov, Sergey N.
, (2017)
Derivatives of methylenediphosphonic acid possess wide spectra of biological activities and are used in enzymology as research tools as well as in practical medicine. Carbonyl diphosphonic acid is a promising starting building block for synthesis of functionally substituted methylenediphosphonates. Investigation of the interaction of carbonyl diphosphonic acid with hydroxylamine clearly demonstrates that it is impossible to isolate oxime within the pH range 2–12, while only cyanophosphonic and phosphoric acids are the products of the fast proceeding Beckmann-like fragmentation. In the case of O-alkylhydroxylamines, corresponding alcohols are found in the reaction mixtures in addition to cyanophosphonic and phosphoric acids. Therefore, two residues of phosphonic acid being attached to a carbonyl group provide new properties to this carbonyl group, making its oximes very unstable. This principally differs carbonyl diphosphonic acid from structurally related phosphonoglyoxalic acid and other α-ketophosphonates.
Lithiation of diethyl trichloromethylphosphonate and the transformations of the α-lithiated derivative
Perlikowska, Wieslawa,Modro, Agnes M.,Modro, Tomasz A.,Mphahlele, Malose J.
, p. 2611 - 2613 (1996)
The lithiation of diethyl trichloromethylphosphonate below -100 °C leads to a stable α-lithiated derivative, but at temperatures of about -80 °C the lithiation is accompanied by spontaneous reactions leading to tetraethyl (chloromethylene)bisphosphonate as the exclusive product. Possible mechanisms of the reaction are discussed.
Partial esters of (Di) chloromethanediphosphonic acid useful for treating disorders relating to the metabolism of calcium
-
, (2008/06/13)
Novel pharmaceutically active bisphosphonic acid derivatives of formula (I), in which R1, R2, R3 and R4 independently are C1 -C22 -alkyl, C2 -C22 -alkenyl, C2 -C22 -alkynyl, C3 -C10 -cycloalkyl, C3 -C10 -cycloalkenyl, aryl, aralkyl, silyl and hydrogen, and R4 is different from hydrogen, Q1 is hydrogen, fluorine, chlorine, bromine or iodine, and Q2 is chlorine, bromine or iodine, including the stereoisomers, such as the geometrical isomers and optically active isomers, of the compounds, as well as the pharmaceutically acceptable salts of the compounds. STR1
SYNTHESIS AND HIV-1 REVERSE TRANSCRIPTASE INHIBITION ACTIVITY OF FUNCTIONALIZED PYROPHOSPHATE ANALOGUES
McKenna, Charles E.,Khare, Anil,Ju, Jing-Yue,Li, Zeng-Min,Duncan, Greg,et al.
, p. 139 - 142 (2007/10/02)
A new approach, ketone derivatization, for introducing desired functionality into the α-keto pyrophosphate analogues oxophosphonoacetic acid (COPAA) and oxomethanediphosphonic acid (COMDP) is exemplified in the synthesis of several COPAA and COMDP hydrazones with specific functional groups.The preparation of tetraalkyl COMDP esters is also described.Inhibition of HIV-1 reverse transcriptase (isolated enzyme) and of p24 production by HIV-1 (virus-infected H9 cells) by hydrazone derivatives of COPAA and COMDP is briefly discussed.
Bisphosphonic Compounds. Part 3. Preparation and Identification of Tetraalkyl Methylene- and (α-Halomethylene)bisphosphonates by Mass Spectrometry, NMR Spectroscopy and X-Ray Crystallography
Vepsaelaeinen, Jouko,Nupponen, Heikki,Pohjala, Esko,Ahlgren, Markku,Vainiotalo, Pirjo
, p. 835 - 842 (2007/10/02)
The preparation and identification of tetraalkyl methylenebisphosphonates (XYC2; X = Y = H, Cl or Br and R = alkyl) have been studied.Detailed procedures are given for the synthesis of XYC2 (X = Y = H; R = hexyl; X = Y = Cl or Br and R = Me). 1H, 13C and 31P NMR data are reported including 1JCH, 2JCP', 3JCP and 2JPP coupling constants.The fragmentation of 19 XYC2 has been studied in the gas phase.The solid state structures are given for two compounds (X = Y = Cl, R = Pri and X = Y = Br, R = Me).
SYNTHESIS OF α-HALOGENATED METHANEDIPHOSPHONATES
McKenna, Charles E.,Khawli, Leslie A.,Ahmad, Wan-Yaacob,Pham, Phuong,Bongartz, Jean-Pierre
, p. 1 - 12 (2007/10/02)
Methanediphosphonate (MDP) anions can exhibit anti-viral activity, inhibit bone resorption, and act as ligands in radiopharmaceuticals. α-Halo-substitution provides MDP derivatives (XYMPD, where X = H, F, Cl or Br; Y = F, Cl or Br) with modified acid-base, steric and other properties.These compounds are conveniently made from the corresponding α-halogenated XYMDP esters (RO)2P(O)CXYP(O)(OR)2.Detailed procedures are given for synthesis of R4XYMDP for R = Pri and X, Y = H, Cl; Cl, Cl; H, Br; Br, Br; F, Cl; F, Br and Cl, Br in 88-96percent yield; for R = Et and X, Y = H, Cl; Cl, Cl; H, Br; Br, Br and Cl, F in 81-94percent yield; and for R = Me and X, Y = Cl, Cl and Br, Br in 72-80percent yield.NMR data (1H, 31P,13C, (19F)) are presented for the products obtained.The XYMDP acids (X, Y = H, Cl; Cl, Cl; H, Br; Br, Br; F, Cl; F, Br and Cl, Br) were prepared by HCl hydrolysis of a corresponding ester and characterized as tris(dicyclohexylammonium) salts by elemental analyses and 31P NMR.
