Phosphonate Research Articles

Pd(Ar‐BIAN)(alkene)]‐Catalyzed Highly Chemo‐, Regio‐, and Stereoselective Semihydrogenation of 1,2‐Allenyl Phosphonates and Related Compounds.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract, please click on HTML or PDF.

Synthesis of the Dimethyl Ester of 1‐Deoxy‐L‐idonojirimycin‐1‐methylenephosphonate: A New Approach to Iminosugar Phosphonates.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract, please click on HTML or PDF.

Reactions of 1,3-dicarbonyl compounds with (chloroethynyl)phosphonates

Reactions of 1,3-dicarbonyl compounds with (chloroethynyl)phosphonates

Pd(Ar‐BIAN)(alkene)]‐Catalyzed Highly Chemo‐, Regio‐, and Stereoselective Semihydrogenation of 1,2‐Allenyl Phosphonates and Related Compounds

Pd(Ar‐BIAN)(alkene)]‐Catalyzed Highly Chemo‐, Regio‐, and Stereoselective Semihydrogenation of 1,2‐Allenyl Phosphonates and Related Compounds

Pd(Ar‐BIAN)(alkene)]‐Catalyzed Highly Chemo‐, Regio‐, and Stereoselective Semihydrogenation of 1,2‐Allenyl Phosphonates and Related Compounds

Ansonsten schwer fassbare trisubstituierte (Z)-1-Alkenylphosphonate erhält man durch partielle Hydrierung von Allenylphosphonaten in Gegenwart des Pd-Komplexes 1. Viele dieser Reaktionen zeichnen sich durch hohe Ausbeuten, Chemo-, Regio- und Stereoselektivitäten aus. Ähnlich funktionalisierte Allene sind gleichfalls geeignet und liefern die entsprechenden Z-konfigurierten Alkene (siehe Schema). R1=H, Alkyl, Aryl, Benzyl; R2,R3=H, Alkyl; FG=P(O)(OR)2, P(O)Ph2, SO2Ph, COOEt.

Reaction of chloromethyliso(thio)cyanato(thio)phosphonates(-phosphinates) with phenol, ethanol, and thiols

(Chloromethyl)isocyanatophosphonates(-phosphinates) take up phenol to form carbamates whose β-cleavage gives rise to phenyl (chloromethyl)phosphonates(-phosphinates). (Chloromethyl)(thio)phosphinic-(phosphonic) isothiocyanates react with phenol at 20°C in the absence of catalyst to afford phenyl phosphinates(-phosphonates). (Alkylsulfanyl)carbamates formed by addition of thiols to (chloromethyl)iso(thio)cyanastophosphonates(-phosphinates) under the action of an equimolar amount of triethylamine undergo cyclization into 1,3,4-oxaza(thiaza)phospholines.

Substrates for Cell Adhesion Prepared via Active Site-Directed Immobilization of a Protein Domain

Recent studies in basic cell biology and bioengineering call for model substrates that present active proteins, with control over protein density, pattern, and orientation, to more directly mimic the natural extracellular matrix. Herein we demonstrate a strategy for controlled, irreversible immobilization of a cell adhesion protein domain onto an otherwise bioinert substrate with well-defined protein orientation and density. Our approach uses a tri(ethylene glycol)-terminated self-assembled monolayer presenting a phosphonate ligand that is used to immobilize an engineered fusion protein. One component of the fusion protein, the 22 kDa serine esterase cutinase, reacts with the surface-bound ligand to form a site-specific covalent adduct, and the second component of the fusion protein is therefore immobilized on the surface. Here we use this approach to immobilize an engineered version of the 12 kDa 10th domain of fibronectin III (FnIII10Eng) to direct cell adhesion. Substrates presenting this protein media...

Synthesis and Properties of Poly(Styrene‐co‐Phosphonate‐Containing Maleimide)

Soluble copolymers of diethyl(p‐(N‐phenyl)maleimide)phosphonate (4P), diphenyl (p‐(N‐phenyl)maleimide)phosphonate (PP), diethyl(p‐(N‐(2′,6′‐dibromophenyl)maleimide) phosphonate) (BrP) with styrene (St) were synthesized by radical polymerization in toluene at 70°C using 2,2′‐azobisisobutyronitrile (AIBN) as initiator. The comonomer reactivity ratios were calculated by the conventional Fineman‐Ross, Joshi‐Joshi, and Kelen‐Tüdos methods. The glass transition temperatures (T gs) and thermal degradation of copolymers were determined by differential scanning calorimetric (DSC) and thermo‐gravimetric analysis (TGA) methods, respectively. The introduction of phosphonate side‐chain into maleimide (MI) monomers changed the comonomer reactiviy ratio with St from an alternating to azeotropic copolymerization. The curves of T gs vs. the different compositions of the above synthesized MI–St copolymers matched the modified Johnston's equation as increasing the affect of weight ratio on alternating‐segment, and exhibited an S‐shaped curve of deviation in comparison with the Fox's equation. As the azeotropic composition of the above copolymers nearby Fox's equation, their thermal stability and flame retardancy could be enhanced simultaneously by the synergy effect of their comonomers. Furthermore, a rigid structure or polar bromine atom within the phosphonate‐containing MI segment of copolymer also could further promote its thermal stability and flame retardancy.

Cyclization of Allenyl Phosphonates to 3‐Chloro‐4‐(diethylphosphono)‐2,5‐dihydrofurans Induced by CuCl2.

3-Chloro-4-(diethylphosphono)-2,5-dihydrofurans5a–fwere synthesised by the reaction of 1-(hydroxymethyl)allenyl phosphonates with CuCl 2 .

Cyclization of allenyl phosphonates to 3-chloro-4-(diethylphosphono)-2,5-dihydrofurans induced by CuCl 2

3-Chloro-4-(diethylphosphono)-2,5-dihydrofurans5a–fwere synthesised by the reaction of 1-(hydroxymethyl)allenyl phosphonates with CuCl 2 .

Curative treatments trialed on young grapevines infected with Phaeomoniella chlamydospora

Internal symptoms of Petri disease include brown wood-streaking and an abnormally dark pith, caused by Phaeomoniella chlamydospora (Pch). This paper reports on the effect of eight fungicides and a hot water treatment on naturally infected one-year-old Pinot Noir rootlings in a glasshouse trial. Vines were destructively assessed 22 weeks after planting. All treatments significantly reduced the incidence of dark pith. Phosphonate treatment was the most effective and benzothiodiazole was the least effective treatment with respect to controlling Pch. These results will contribute to the development of an integrated management program for grapevine propagating material.

A New and Efficient Electrosynthesis of 2-Substituted 1,1-Cyclopropanediylbis(phosphonates)

A New and Efficient Electrosynthesis of 2-Substituted 1,1-Cyclopropanediylbis(phosphonates)

Synthesis and Biological Evaluation of Phosphonate Derivatives of Some Acyclic Pyridine-C-Nucleosides

Abstract

Synthesis and Characterization of New Cα,α-Disubstituted (Diarylaminomethyl)-phosphonates

Synthesis and Characterization of New Cα,α-Disubstituted (Diarylaminomethyl)-phosphonates

Synthesis of N-(alkoxycarbonyl or alkoxycarbonyl-methyl-alkoxyphosphonyl)-α-amino-O, O-diphenyl phosphonates and their bioactivities

Synthesis of N-(alkoxycarbonyl or alkoxycarbonyl-methyl-alkoxyphosphonyl)-α-amino-O, O-diphenyl phosphonates and their bioactivities

Synthesis of N-(alkoxycarbonyl or alkoxycarbonyl-methyl-alkoxyphosphonyl)-α-amino-O,O-diphenyl phosphonates and their bioactivities

With phosphonoformic acid (PFA) and its analog, phosphonoacetic acid (PAA), as the lead compounds, α-amino phosphonates were introduced into PFA and PAA. The derivatives of N-(alkoxycarbonyl-alkoxyphosphonyl)-α-amino phosphonates (I) and N-(alkoxycarbonyl-methyl-alkoxyphosphonyl)-α-amino phosphonates (II) with the N-terminal of amino phosphonates bonding to phosphorus atom of PFA andPAA were synthesized via the reaction of the corresponding phosphonyl chloride with α-amino phosphonates in the presence of a base. The31P NMR spectra of I and II were determined. It is found that the coupling constants3 J pp with R3 being alkyl group were lower than those with R3 being (substituted) phenyl, and this result was discussed. The preliminary bioassay showed that some of the compounds I and II have better activities against tobacco mosaic virus (TMV). The inhibitory was higher than that of DHT (2, 4-dioxyhexahydro-1, 3, 5-triazine). In addition, some of the compounds showed the activity against cancer cells.

1,1,3,3,3‐Pentafluoro‐2‐pentafluorophenylpropene oxide. Precursor for novel phosphonates and ylides

1,1,3,3,3‐Pentafluoro‐2‐pentafluorophenylpropene oxide. Precursor for novel phosphonates and ylides

Global analysis of proteins synthesized during phosphorus restriction in Escherichia coli.

The pattern of proteins synthesized in Escherichia coli during steady-state growth in media with ample inorganic phosphate (Pi), upon limitation for Pi (without an alternative phosphorous compound), and during steady-state growth in media containing phosphonate (PHN) as the sole P source was examined by two-dimensional gel electrophoresis. Of 816 proteins monitored in these experiments, all those with differential synthesis rates greater than 2.0 or less than 0.5 upon phosphate limitation (P limitation) or during growth on PHN compared with their rates in the cultures with Pi were classified as belonging to the PL or PHN stimulon, respectively. The PL stimulon included 413 proteins, 208 showing induced synthesis and 205 showing repressed synthesis. The PHN stimulon was smaller: it included 257 proteins; 227 showed induced synthesis and 30 showed repressed synthesis. The overlap of the two stimulons included 137 proteins: most (118) were ones showing induced synthesis. The promoter regions of genes for several of the proteins with induced or repressed synthesis contained sequences which resembled the consensus sequence for PhoB binding. The aggregate mass of proteins responding to P limitation or growth on PHN was 30 to 40% of the cells' total mass. By comparing the proteins responding to P limitation with those responding to growth on PHN, one can speculate which proteins are likely involved in adapting cells to new P sources or in preparing cells to survive stationary phase.

Isothiocyanatochloromethylphosphonates and Phosphinates - Versatile Synthones for Obtaining of S (Se), N, P-Containing Heterocycles

Abstract Isothiocyanatochloromethyl(thio)phosphonates and (thio)-phosphinates 1 (X=O, S; R1 = OPh, CH2Cl, NCS; R2 = H, Cl have been found to be convenient starting material for synthesis of a variety of S (Se), N, P-containing cyclic compounds. They react with different proton containing nucleophiles in the presence of a base with formation of saturated 2 and unsaturated 3 five membered phosphacyclanes. Diisothiocyanatodichloromethylphosphonates 1 (R1 = NCS, R2 =Cl) produce with amines and thiols appropriate bicyclic compounds 4.

A molecular dynamics study of the three-dimensional model of human synovial fluid phospholipase A2--transition state mimic complexes.

Different modes of binding of transition state mimics: amide, phosphonate and difluoro ketone, to human synovial fluid phospholipase A2 (HSF PLA2) are studies by molecular dynamics simulations computed in solvent. The results are analysed in the light of primary binding sites. Hydrogen bonding interaction plays an important role for amino acids such as Gly32, Val30, and Glu55, apart from the well known active site residues viz Asp48, Gly25, Gly29, Gly31, His27, His47, Lys62, Phe23, Asn114 and Tyr112. In addition, the hydrogen bonding interaction between Sn-1 tetrahedral phosphonate group of amide and difluoro ketone inhibitors and crystallographic water molecules (H2O 523, H2O 524 and H2O 401) seems to have a significant role. Many of the active site charged residues display considerable movement upon ligand binding. The structural effects of ligand binding were analyzed from RMS deviations of C alpha in the resulting energy-minimized average structures of the receptor-ligand complexes. The values of the RMS deviations differ among the HSF PLA2s, in a pattern that is not the same for the three complexes. This suggests that ligands with different pharmacological efficacies induce different types of conformational changes of the receptor. Our active-orientation model is, at least qualitatively, consistent with experimental data and should be useful for the rational design of more potent inhibitors.