30148-50-6Relevant articles and documents
Phosphinic acid analogues of thiaproline and the related heterocyclic aminophosphinic acids
Hatam,Martens
, p. 2553 - 2559 (1995)
Bis(trimethylsilyl) phosphonite adds in a 1,2 fashion to the C = N bond in 3-thiazolines 3a-d to give after hydrolysis phosphinic acids 5a-d. Starting from 3-oxazines, the corresponding 6a,b phosphinic acids 7a,b were obtained.
Synthesis of Phosphine Analog of Glutamylglcine
Ragulin, V. V.
, p. 1823 - 1824 (2001)
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One-pot synthesis of α-amino phosphinic acids
Ragulin
, p. 142 - 143 (2004)
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Complexes of divalent transition metal ions with bis(aminomethyl)phosphinic acid in aqueous solution and in the solid state
Kubicek, Vojtech,Vojtisek, Pavel,Rudovsky, Jakub,Hermann, Petr,Lukes, Ivan
, p. 3927 - 3938 (2003)
Bis(aminomethyl)phosphinic acid, (NH2CH2)2PO2H (HL), was synthesized using a new procedure. Its coordination ability towards CO(II)/(III), Ni(II), Cu(II) and Zn(II) was studied both in solution and in the solid state. Because of the presence of two nitrogen atoms the ligand exhibits a higher overall basicity than common (aminoalkyl)phosphinic acids. Consequently, the values of the determined stability constants are comparable with those found for (aminoalkyl)phosphonic acids. NMR titrations of Zn(II) point to the interaction of phosphinate with the metal ion in a strong acid solution. The X-ray structures show several coordination modes in the solid state. All-trans-[MCl2(H2L-O)2 (H2O)2]Cl2, where M(II) are Mn(II), Co(II), Ni(II), Cu(II), Zn(II), Ca(II), and Cd(II), crystallized from acid solutions. The central ion is octahedrally coordinated with two phosphinate oxygen atoms, two molecules of water and two chlorides in all-trans arrangement. Amine groups are protonated and non-coordinated. Participation of the donor groups in crystals isolated from neutral solutions depends on the metal ion. All donor atoms are coordinated in monomeric fac-N,N,O-trans-O,O'-[Co(L-N,N,O)2]+. On the other hand, in the zinc(II) complex, two phosphinate oxygen atoms and two amine nitrogen atoms (trans to each other) of two different ligand molecules are coordinated in an equatorial plane and two amino groups of the two other ligand molecules are bound in axial positions. Thus, each molecule of the amino acid forms a five-membered N,O-chelate to one zinc(II) ion and the other amino group is bound to the neighbouring ion creating an infinite chain. Nickel(II) forms a trans-O,O′-[Ni(H2O)2-(L-N,N)2] complex in which the metal ion is chelated by four amine nitrogen atoms forming two six-membered chelates in an equatorial plane and the octahedron is completed with two water molecules at the apical positions. The phosphinate group is not coordinated. The above results point to a relatively low coordination ability of the phosphinate group; however, due to its low pKA, it is able to bind metal ions at lower pH than other coordinating groups do.
Reactions of Unsaturated Ketones with Bis(trimethylsilyl) Hypophosphite
Tatarinov,Kundina,Dobrynin,Mironov
, p. 90 - 95 (2018)
Bis(trimethylsilyl) hypophosphite reacts with unsaturated ketones (methyl vinyl ketone and mesityl oxide) to give, depending on the reaction conditions, 1: 1 or 1: 2 adducts after hydrolysis. It was found that the intramolecular cyclization of the 1: 2 reaction product with mesityl oxide, trimethylsilyl bis(2-methyl-4- oxopentan-2-yl)phosphinate, yields, after hydrolysis, a phosphorinane with exocyclic carbonyl and hydroxyl groups.
Synthesis of a bifunctional monophosphinate DOTA derivative having a free carboxylate group in the phosphorus side chain
Rezanka, Pavel,Kubicek, Vojtech,Hermann, Petr,Lukes, Ivan
, p. 1431 - 1435 (2008)
A new bifunctional cyclen-based ligand, 3-[hydroxy({4,7,10-tris[(tert- butoxycarbonyl)methyl]-1,4,7,10-tetraazacyclododecan-1-yl}methyl)phosphoryl] propanoic acid, was synthesized by alkylation of tri-tert-butyl 1,4,7,10-tetraazacyclododecane-1,4,7-triacetate (t-Bu3DO3A) by ethyl 3-{ethoxy[(mesyloxy)methyl]phosphoryl}propanoate [MsOCH2P(O)(OEt) CH2CH2CO2Et]. The ethyl carboxylate group in the side chain was selectively deprotected to obtain the esterified bifunctional ligand. More efficient syntheses of some phosphinopropanoic acid derivatives were devised and the phosphorus alkylation reagent was prepared starting from hypophosphorus acid or its salt. Georg Thieme Verlag Stuttgart.
Nucleoside H-boranophosphonates: A new class of boron-containing nucleotide analogues
Higashida, Renpei,Oka, Natsuhisa,Kawanaka, Toshihide,Wada, Takeshi
, p. 2466 - 2468 (2009)
A study on the synthesis of nucleoside H-boranophosphonates, a new class of nucleotide analogues having a P→BH3 and a P-H group, via condensation of the corresponding nucleosides with H-boranophosphonate derivatives is described. The Royal Soci
Covalent Inhibition of Bacterial Urease by Bifunctional Catechol-Based Phosphonates and Phosphinates
Pagoni, Aikaterini,Grabowiecka, Agnieszka,Tabor, Wojciech,Mucha, Artur,Vassiliou, Stamatia,Berlicki, ?ukasz
, p. 404 - 416 (2021/01/13)
In this study, a new class of bifunctional inhibitors of bacterial ureases, important molecular targets for antimicrobial therapies, was developed. The structures of the inhibitors consist of a combination of a phosphonate or (2-carboxyethyl)phosphinate functionality with a catechol-based fragment, which are designed for complexation of the catalytic nickel ions and covalent bonding with the thiol group of Cys322, respectively. Compounds with three types of frameworks, including β-3,4-dihydroxyphenyl-, α-3,4-dihydroxybenzyl-, and α-3,4-dihydroxybenzylidene-substituted derivatives, exhibited complex and varying structure-dependent kinetics of inhibition. Among irreversible binders, methyl β-(3,4-dihydroxyphenyl)-β-(2-carboxyethyl)phosphorylpropionate was observed to be a remarkably reactive inhibitor of Sporosarcina pasteurii urease (kinact/KI = 10 420 s-1 M-1). The high potential of this group of compounds was also confirmed in Proteus mirabilis whole-cell-based inhibition assays. Some compounds followed slow-binding and reversible kinetics, e.g., methyl β-(3,4-dihydroxyphenyl)-β-phosphonopropionate, with Ki? = 0.13 μM, and an atypical low dissociation rate (residence time τ = 205 min).
One-pot synthesis of phosphinylphosphonate derivatives and their anti-tumor evaluations
Deschamp, Julia,Dussart-Gautheret, Jade,Lecouvey, Marc,Legigan, Thibaut,Migianu-Griffoni, Evelyne,Monteil, Maelle
, (2021/12/24)
This paper reports on the synthesis of new hydroxymethylene-(phosphinyl)phosphonates (HMPPs). A methodology has been developed to propose an optimized one-pot procedure without any intermediate purifications. Various aliphatic and (hetero)aromatic HMPPs were synthesized in good to excellent yields (53–98%) and the influence of electron withdrawing/donating group substitution on aromatic substrates was studied. In addition, the one-pot synthesis of HMPP was monitored by31P NMR spectroscopy, allowing effective control of the end of the reaction and identification of all phosphorylated intermediate species, which enabled us to propose a reaction mechanism. Optimized experimental conditions were applied to the preparation of biological relevant aminoalkyl-HMPPs. A preliminary study of the complexation to hydroxyapatite (bone matrix) was carried out in order to verify its lower affinity towards bone compared to bisphosphonate molecules. Moreover, in vitro anti-tumor activity study revealed encouraging antiproliferative activities on three human cancer cell lines (breast, pancreas and lung).
