A microwave-assisted synthesis of dialkyl and cyclic H-phosphonates via bis(2,2,2 trifluoroethyl) phosphonate (BTFEP) is described. This method enables the synthesis of various cyclic H-phosphonates and hetero-substituted dialkyl H-phosphonates by si...
The continuous flow alcoholysis of dialkyl H-phosphonates by aliphatic alcohols in the absence of a catalyst was elaborated using a microwave (MW) reactor equipped with a flow cell. By the precise control of the reaction conditions, the synthesis cou...
Naturally occurring phospholipids, such as phosphatidyl glycerol (PG), are gaining interest due to the roles they play in disease mechanisms. To elucidate the metabolism of PG, an optically pure material is required, but this is unfortunately not com...
H-phosphonates, H-phosphinates and secondary phosphine oxides may be preligands, and are important building blocks in the synthesis of pharmaceuticals, pesticides, and P-ligands. The prototropic tautomerism influenced by substituent effects plays an...
The chemical synthesis of DNA and RNA is universally carried out using nucleoside phosphoramidites or H-phosphonates as synthons. This review focuses on the phosphorus chemistry behind these synthons and how it has been developed to generate procedur...
Synthesis of spacer-armed pseudodi-, pseudotetra-, and pseudohexasaccharides related to the capsular phosphoglycan of Haemophilus influenzae type a, the second most virulent serotype of H. influenzae (after type b), was performed for the first time v...
The microwave (MW)-assisted direct esterification of phenyl-H-phosphinic acid, transesterification of the alkyl phenyl-H-phosphinates so obtained, and the similar reaction of dibenzyl phosphite (DBP) were investigated in detail, and the batch accompl...
We have developed a robust solid-phase protocol which allowed the synthesis of chimeric oligonucleotides modified with phosphodiester and O-methylphosphonate linkages as well as their P-S and P-N variants. The novel O-methylphosphonate-derived modifi...
The synthesis of novel 3,4-dihydropyrimidin-2(1H)-one-phosphonates was elaborated by the microwave (MW)-assisted three-component Biginelli reaction of β-ketophosphonates, aromatic or aliphatic aldehydes and urea derivatives. The condensation was...
Synthesis of 5''-phosphate 2'-O-ribosylribonucleosides [Nr(p)] of four common ribonucleosides, and 3'-phosphoramidites of 5''-phosphate 2'-O-ribosyladenosine and 2'-O-ribosylguanosine using the H-phosphonate chemistry is described. An additional rin...
Voltammetry provides important information on the redox properties of catalysts (transition metal complexes of Ni, Co, Mn, etc.) and their activity in electrocatalytic reactions of aromatic C–H phosphonation in the presence of a phosphorus prec...
This work reports a straightforward regioselective synthetic methodology to prepare α-aminophosphine oxides and phosphonates through the addition of oxygen and sulfur nucleophiles to the C–N double bond of 2H-azirine derivatives. Determin...
Organophosphorus compounds play an important role in the medicinal- or agricultural industry, and in the human body as well. Over the last years, heterocyclic phosphonates have received growing interest due to their potential biological activity. An...
Phosphorous, in the form of phosphate, is a key element in the nutrition of all living beings. In nature, it is present in the form of phosphate salts, organophosphates, and phosphonates. Bacteria transport inorganic phosphate by the high affinity ph...
Coumarins are an important class of natural heterocyclic compounds that have attracted considerable synthetic and pharmacological interest due to their various biological activities. This review emphasizes on the synthetic methods for the preparation...
Herein, silicon-protected, ortho-methylated hydroxy-pyridines were reported as initiators in 2-aminoalkoxy-bis(phenolate)yttrium complexes for rare earth metal-mediated group-transfer polymerization (REM-GTP) of Michael-type monomers. To introduce th...
Three 1,4,7,10-tetraazacyclododecane-based ligands disubstituted in 1,4-positions with phosphonic acid, phosphonate monoethyl-ester, and H-phosphinic acid pendant arms, 1,4-H4do2p, 1,4-H2do2pOEt, and 1,4-H2Bn2do2pH, were synthesized and their coordin...
Cellular NAD(P)H-dependent oxidoreductase activity with artificial dyes (NAD(P)H-OR) is an indicator of viability, as the cellular redox state is important for biosynthesis and antioxidant defense. However, high NAD(P)H due to impaired mitochondrial...
A new Co(II) phosphonate, Co(H2O)2PO3C–C12H9·H2O, has been synthesized under hydrothermal conditions. The monoclinic P21/c structure of this organic–inorganic hybrid consists of isolated perovskite-type chains of corner-shared CoO4...
The title compound, diethyl [(4-{(9H-carbazol-9-yl)methyl}-1H-1,2,3-triazol-1-yl)(benzamido)methyl]phosphonate, was synthesized with excellent yield and high regioselectivity through 1,3-dipolar cycloaddition reaction between the α-azido diethy...
The pH-dependent binding strengths and modes of the organometallic [(η6-p-cym)M(H2O)3]2+ (MII = Ru, Os; p-cym = 1-methyl-4-isopropylbenzene) or [(η5-Cp*)M(H2O)3]2+ (MIII = Rh, Ir; Cp* = pentamethylcyclopentadienyl anion) cations towards imino...
Phosphorus-modified prodrugs of dideoxynucleoside triphosphates (ddNTPs) have shown promise as pronucleotide strategies for improving antiviral activity compared to their parent dideoxynucleosides. Borane modified NTPs offer a promising choice as nuc...
An enzymatic route for phosphorous-carbon- bond formation is developed by discovering new promiscuous activity of lipase. This biocatalytic transformation of phosphorous-carbon- bond addition leads to biologically and pharmacologically relevant &alph...
Publications covering a new easy metal-free functionalization of pyridinoids (pyridines, quinolines, isoquinolines, acridine) under the action of the system of electron-deficient acetylenes (acetylenecarboxylic acid esters, acylacetylenes)/P-nucleoph...
Flame retardants play a crucial role in mitigating the hazards associated with fires by impeding their ignition and spread. However, conventional halogen-based flame retardants have encountered environmental and health concerns due to their persisten...
Using a novel strategy, amphiphilic polyphosphoesters based on poly(oxyethylene H-phosphonate)s (POEHP) with different poly(ethylene glycol) segment lengths and aliphatic alcohols with various alkyl chain lengths were synthesized using polycondensati...
Multistep one-pot polycondensation reactions synthesized amphiphilic diblock polyphosphoesters containing lactic acid units in the polymer backbone. At the first step was synthesized poly[poly(ethylene glycol) H-phosphonate–b-poly(ethylene glyc...
A series of 5′-phosphorylated (dialkyl phosphates, diaryl phosphates, phosphoramidates, H-phosphonates, phosphates) 1,2,3-triazolyl nucleoside analogues in which the 1,2,3-triazole-4-yl-β-D-ribofuranose fragment is attached via a methylene...
Synthesis of intermediate containing P(O)-Cl bonds is the key to converting P(O)-H bonds to P(O)-N. In this work we have performed chlorination reactions of different H-phosphinates and H-phosphonates using N-chlorosuccinimide as an environmentally-b...
Nowadays, increasing attention is devoted to the search for polymeric composite materials that are characterized by reduced flammability. In this work, the layer-by-layer (LbL) technique was applied to form multilayered protective coatings for polyam...
In the present study, for the first time, a biodegradable and non-toxic polyphosphoramidate glycohydrogel (PPAGHGel) was prepared by crosslinking a polyphosphoramidate glycoconjugate (PPAG) with hexamethylene diisocyanate (HMDI) under mild conditions...
The new linker molecule 4-phosphono-biphenyl-4′-carboxylic acid (H2O3P-(C6H4)2-COOH, H3BPPA) has been structurally elucidated in hydrogen-bonded networks with the ammonium cation NH4(H2BPPA)(H3BPPA) (1) and the hexaamminecobalt(III) cation [Co(NH3)6]...
Short and efficient syntheses of functionalized (pyrrolidin-2-yl)phosphonate and (5-oxopyrrolidin-2-yl)phosphonate have been developed. The synthetic strategy involved the diastereospecific 1,3-dipolar cycloaddition of N-benzyl-C-(diethoxyphosphoryl)...
Phosphonate ligands demonstrate strong affinity for metal ions. However, there are several cases where the phosphonate is found non-coordinated to the metal ion. Such compounds could be characterized as salts, since the interactions involved are ioni...
9,9-dimethylfluorenyl-2-phosphonic acid 1 was reacted with manganese nitrate tetrahydrate to produce under hydrothermal conditions the crystalline manganese phosphonate Mn(H2O)2[O2(OH)PC15H13]2·2H2O which crystallize in the P21/c space group....
In this study we report the synthesis of C5/C6-fused uridine phosphonates that are structurally related to earlier reported allosteric P2Y2 receptor ligands. A silyl-Hilbert-Johnson reaction of six quinazoline-2,4-(1H,3H)-dione-like base moieties wit...
In this study, perfluorinated phosphonic acid modifications were utilized to modify zinc oxide (ZnO) nanoparticles because they create a more stable surface due to the electronegativity of the perfluoro head group. Specifically, 12-pentafluorophenoxy...
Phosphonates are widely used as antiscalants for softening processes in drinking water treatment. To prevent eutrophication and accumulation in the sediment, it is desirable to remove them from the membrane concentrate before they are discharged into...
Starting from enantiomeric pure 1-[(3S,5R)- and 1-[(3R,5S)-3-(hydroxymethyl)-2-methylisoxazolidin-5-yl]-5-methylpyrimidine-2,4(1H,3H)-diones (−)7a and (+)7b, obtained by lipase-catalyzed resolution, pure diethyl{[(3S,5R)-2-methyl-5-(5-methyl-2,4-dio...
In the search for new antitumor agents, aminophosphonic acids and their derivatives based on octahydroquinoxalin-2(1H)-one scaffold were obtained and their cytotoxic properties and a mechanism of action were evaluated. Phosphonic acid and phosphonate...
Novel 1,2,3-triazol-5-yl-phosphonates were prepared by the copper(I)-catalyzed domino reaction of phenylacetylene, organic azides and dialkyl phosphites. The process was optimized on the synthesis of the dibutyl (1-benzyl-4-phenyl-1H-1,2,3-triazol-5-...
Two crystals of N,N′-bis(phosphonomethyl)-1,4,5,8-naphthalenediimide were grown in the presence of neutral (water) and charged (imidazolium cation) species, yielding [(H2O3P)CH2-(C14H4N2O4)-CH2(PO3H2)]∙H2O (1) and [C3H5N2][(H1.5O3P)CH2-(C...
Phosphonates derivatives are compounds of interests and are applied as drugs of, e.g., antibacterial antiviral activities, connected with their inhibitory activity towards different enzymes, which is related to the configuration of particular compoun...
By treating a suitable Wittig reagent under acid conditions, the phosphonate ester 1,4-bimethylenebenzene phosphonate ethyl ester (H2[BBPE], 1) was obtained. As a building block, compound 1 has been reacted with the Lewis-base N,N-dimethylpiperazine,...
Two isostructural lanthanide amino-phosphonate complexes [Ln10(μ3-OH)3(µ-OH)(CO3)2(O2CtBu)15(O3PC6H10NH2)3(O3PC6H10NH3)2(H2O)2][Et2NH2] (Ln = Gd(III), 1 and Tb(III), 2) have been obtained through reflux reactions of lanthanide pivalates with...
The present contribution reports on the synthesis via reversible addition-fragmentation chain transfer (RAFT) polymerization of a methacrylate derivative bearing an aminobisphosponate moiety as a pendant group, namely, ethyl N,N-tetramethylbis(phosph...
Selective depression of serpentine remains a major challenge in the flotation of low-grade nickel sulphide ores because serpentine slimes impair concentrate grade and recovery. In this study, four structurally related micromolecular depressants beari...
A library of novel phosphonic acid analogues of homophenylalanine and phenylalanine, containing fluorine and bromine atoms in the phenyl ring, have been synthesized. Their inhibitory properties against two important alanine aminopeptidases, of human...
A series of novel chiral thioureas 3a-n bearing leucine and phosphonate moieties were synthesized in excellent yields. The structures of the compounds were completely characterized by elemental analysis, IR, 1H-, 13C-, 31P- and 19F-NMR spectral data....
Aminophosphonates such as aminotris(methylenephosphonic acid) (ATMP) are common constituents of antiscalants. In nanofiltration (NF) and reverse osmosis (RO) processes, ATMP prevents inorganic scaling leading to more stable membrane performance. So f...
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