- New dinuclear nickel(II) complexes: Synthesis, structure, electrochemical, and magnetic properties
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The reaction of [NiBr2(bpy)2] (bpy = 2,2′-bipyridine) with organic phosphinic acids ArP(O)(OH)H [Ar = Ph, 2,4,6-trimethylphenyl (Mes), 9-anthryl (Ant)] leads to the formation of binuclear nickel(II) complexes with bridging ArP(H)Osu
- Yakhvarov, Dmitry,Trofimova, Ekaterina,Sinyashin, Oleg,Kataeva, Olga,Budnikova, Yulia,Loennecke, Peter,Hey-Hawkins, Evamarie,Petr, Andreas,Krupskaya, Yulia,Kataev, Vladislav,Klingeler, Ruediger,Buechner, Bernd
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Read Online
- Synthesis and evaluation of phosphorus containing, specific CDK9/CycT1 inhibitors
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Although there is a significant effort in the design of a selective CDK9/CycT1 inhibitor, no compound has been proven to be a specific inhibitor of this kinase so far. The aim of this research was to develop novel and selective phosphorus containing CDK9/CycT1 inhibitors. Molecules bearing phosphonamidate, phosphonate, and phosphinate moieties were synthesized. Prepared compounds were evaluated in an enzymatic CDK9/CycT1 assay. The most potent molecules were tested in cell-based toxicity and HIV proliferation assays. Selectivity of shortlisted compounds against CDKs and other kinases was tested. The best compound was shown to be a highly specific, ATP-competitive inhibitor of CDK9/CycT1 with antiviral activity.
- Németh, Gábor,Greff, Zoltán,Sipos, Anna,Varga, Zoltán,Székely, Rita,Sebestyén, Mónika,Jászay, Zsuzsa,Béni, Szabolcs,Nemes, Zoltán,Pirat, Jean-Luc,Volle, Jean-No?l,Virieux, David,Gyuris, ágnes,Kelemenics, Katalin,áy, éva,Minarovits, Janos,Szathmary, Susan,Kéri, Gy?rgy,Orfi, László
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p. 3939 - 3965
(2014/06/09)
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- Phosphonothioate hydrolysis by molybdocene dichlorides: Importance of metal interaction with the sulfur of the thiolate leaving group
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The metallocene bis(cyclopentadienyl)molybdenum(IV) dichloride Cp 2MoCl2 hydrolyzes O,S-diethyl phenylphosphonothioate (1) with only P-S scission to yield a phosphonate under mild aqueous conditions. In terms of degrading phosphonoth
- Kuo, Louis Y.,Baker, Devon C.,Dortignacq, Adria K.,Dill, Kristina M.
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p. 4759 - 4765
(2013/09/24)
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- Revisited synthesis of aryl-H-phosphinates
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A systematic study of the reaction conditions for the preparation of pure aryl-H-phosphinate esters, originally developed by Sander and optimized by Petnehazy, is reported. The influence of the reaction concentration has been investigated for the formation of phosphonite intermediates via direct addition of triethyl phosphite to the appropriate Grignard reagent. Subsequent hydrolysis of the phosphonites under acidic conditions gives various aryl-H-phosphinates in high yields and purities. Georg Thieme Verlag Stuttgart, New York.
- Volle, Jean-Noel,Filippini, Damien,Midrier, Camille,Sobecki, Michal,Drag, Marcin,Virieux, David,Pirat, Jean-Luc
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body text
p. 2490 - 2494
(2011/09/20)
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- Efficient synthesis of mono- and diarylphosphinic acids: a microwave-assisted palladium-catalyzed cross-coupling of aryl halides with phosphinate
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A general, efficient method for the microwave-assisted synthesis of mono- and diarylphosphinic acids from anilinium phosphinate and aryl halides, using Pd(0) and Xantphos as a supporting ligand, was developed.
- Kalek, Marcin,Stawinski, Jacek
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experimental part
p. 10406 - 10412
(2010/02/27)
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- Proline/pipecolinic acid-promoted copper-catalyzed P-arylation
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We have developed a convenient and efficient approach for P-arylation of organophosphorus compounds containing P-H. Using commercially available and inexpensive proline and pipecolinic acid as the ligands greatly improved the efficiency of the coupling reactions, so the method can provide an entry to arylphosphonates, arylphosphinates and arylphosphine oxides.
- Huang, Cheng,Tang, Xu,Fu, Hua,Jiang, Yuyang,Zhao, Yufen
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p. 5020 - 5022
(2007/10/03)
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- A versatile and efficient ligand for copper-catalyzed formation of C-N, C-O, and P-C bonds: Pyrrolidine-2-phosphonic acid phenyl monoester
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A new and readily available bidentate ligand, namely, pyrrolidine-2- phosphonic acid phenyl monoester (PPAPM), has been developed for the copper-catalyzed formation of C-N, C-O, and P-C bonds, and various N-, O-, and P-arylation products were synthesized in good to excellent yields by using the CuI/PPAPM catalyst system. Addition of the PPAPM ligand greatly increases the reactivity of the copper catalyst, and the resulting versatile and efficient catalyst system is of widespread and practical application in cross-coupling reactions.
- Rao, Honghua,Jin, Ying,Fu, Hua,Jiang, Yuyang,Zhao, Yufen
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p. 3636 - 3646
(2008/02/03)
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- Recent advances in phosphorus-carbon bond formation: Synthesis of H-phosphinic acid derivatives from hypophosphorous compounds
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This account summarizes the research conducted in our laboratory over the past five years. New methodologies were devised for the formation of P-C bonds with a focus on the reactions of hypophosphorous acid derivatives. Three types of reactions have been developed: palladium-catalyzed cross-coupling, room-temperature radical addition, and palladium-catalyzed addition. Our results are summarized in each of these areas and include some of our most recent data. (1) Our palladium-catalyzed cross-coupling has been extended to the direct coupling of alkyl phosphinates with a variety of aryl, heteroaryl, and even alkenyl electrophiles. (2) The addition of sodium hypophosphite under radical conditions is extended from alkenes to alkynes. (3) The catalytic addition of hypophosphorous compounds using palladium catalysts (hydrophosphinylation) is also discussed.
- Montchamp, Jean-Luc
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p. 2388 - 2406
(2007/10/03)
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- Conversions of 2-phenyl-1,3,2-dioxaphospholane under the action of hydrogen chloride
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The reaction of 2-phenyl-1,3,2-dioxaphospholane with HCl gives a mixture of phenylphosphinic acid, bis(2-chloroethyl) phenylphosphonate, and phenylphosphine; therewith, intermediate oligomeric phosphonites, hydrophosphoryl compounds, and phosphoranes were detected. Thermal treatment of the reaction mixture results in formation of ethylene phenylphosphonate and (2-chloroethyl)phenylphosphinate.
- Lazarev,Bredikhina,Bredikhin
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p. 928 - 932
(2007/10/03)
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- Design and pharmacological activity of phosphinic acid based NAALADase inhibitors
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A novel series of phosphinic acid based inhibitors of the neuropeptidase NAALADase are described in this work. This series of compounds is the most potent series of inhibitors of the enzyme described to date. In addition, we have shown that these compounds are protective in animal models of neurodegeneration. Compound 34 significantly prevented neurodegeneration in a middle cerebral artery occlusion model of cerebral ischemia. In addition, in the chronic constrictive model of neuropathic pain, compound 34 significantly attenuated the hypersensitivity observed with saline-treated animals. These data suggest that NAALADase inhibition may provide a new approach for the treatment of both neurodegenerative disorders and peripheral neuropathies.
- Jackson,Tays,Maclin,Ko,Li,Vitharana,Tsukamoto,Stoermer,Lu,Wozniak,Slusher
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p. 4170 - 4175
(2007/10/03)
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- First Synthesis of Secondary P-Alkenyl and P-Alkynyl Phosphine Oxides
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A general method for preparing secondary P-alkenyl and P-alkynyl phosphine oxides, compounds unknown so far, involves the condensation of the vinyl Grignard reagent or lithium acetylide on P-chloroaminophosphines followed by acidic hydrolysis of the corresponding vinyl or ethynylaminophosphines on a solid acid (Amberlyst 15).The few reported chemical properties are mainly related to the strong PH bond activation.Of special interest is the addition of a secondary vinylphosphine oxide derivative on methyl acrylate which occurs at room temperature without any catalyst.
- Baba, Gnon,Pilard, Jean-Francois,Tantaoui, Khalid,Gaumont, Annie-Claude,Denis, Jean-Marc
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p. 4421 - 4424
(2007/10/02)
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- Experiments on the Generation of 2-Coordinate Phosphoryl Species by Fragmentation of 7-Phosphanorbornene and 3-Phospholene Derivatives
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2,6-Di-tert-butyl-4-methylphenyl phosphenite (ArOP=O) was released into the gas phase on heating a neat sample of a 7-phosphanorbornene derivative 6 bearing this aryloxy substituent at 300 deg C (0.01 mm).Attempts to prepare 1-adamantyl phosphenite simila
- Quin, Louis D.,Jankowski, Stefan,Rudzinski, Juliusz,Sommese, Anthony G.,Wu, Xiao-Ping
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p. 6212 - 6216
(2007/10/02)
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- KINETICS AND MECHANISTIC ASPECTS OF THE HYDROLYSIS REACTION OF CYCLIC PHOSPHONODITHIOITES
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The hydrolysis of the cyclic phosphonodithioite in aqueous acetonitrile follows a rate law that is first order in the concentration of , and independent of the water concentration.The values of Ea, ΔH(excit) and ΔS(excit) are
- Kim, Sangha,Roundhill, D. Max
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- SYNTHESIS AND HYDROLYTIC STABILITY OF SOME NEW PHOSPHONODITHIOITE, PHOSPHONODITHIOATE, AND PHOSPHONOTRITHIOATE ESTERS
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The compounds RP(SCH2CH2CO2CH2CH3)2 (R = (CH3)3C, C6H5) have been prepared from RPCl2 and HSCH2CH2CO2CH2CH3 and base.The compounds react with hydrogen peroxide and with sulfur to give RP(O)(SCH2CH2CO2CH2CH3)2 and RP(S)(SCH2CH2CO2CH2CH3)2 respectively.The 5-membered ring compound has been synthesized from C6H5PCl2 and diethyl 2,3-dimercaptosuccinate and base.The compounds reacts with hydrogen peroxide and with sulfur to give and respectively.Reacting C6H5PCl2 with one equivalent of HSCH2CH2CO2CH2CH3 and base gives C6H5PCl(SCH2CH2CO2CH2CH3), which undergoes hydrolysis to give C6H5PH(O)(SCH2CH2CO2CH2CH3).Except for and C6H5PH(O)(SCH2CH2CO2CH2CH3), the compounds do not undergo significant hydrolytic cleavage of the P-S bond.The hydrolysis of likely proceeds via C6H5PH(O)(SCH(CO2CH2CH3)CH(CO2CH2CH3)SH).The increased hydrolysis rate of C6H5PH(O)(SCH2CH2CO2CH2CH3) is possibly due to hydrogen bonding between water and the PH(O) functionality. Key words: Phosphonodithioite; phosphonodithioate; phosphonotrithioate; hydrogen bonding; NMR spectra.
- Kim, Sangha,Mimikakis, John L.,Roundhill, D. Max
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p. 119 - 128
(2007/10/02)
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- DIPOLE MOMENTS OF SOME PHENYL AND CHLOROPHENYL PHOSPHORUS-HALOGEN COMPOUNDS
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The electric dipole moments of o-ClC6H4PCl2 1, C6H5PF4 2, o-ClC6H4PF4 3, C6H5P(O)F2 4, C6H5P(O)HF 5, C6H5P(O)H(OH) 6, and o-ClC6H4P(O)Cl2 7, were determined in dilute benzene solution at 25 deg C.The phosphoryl bond moment P=O in compounds 4, 5, and 7 was
- Wang, Chengrui,Bock, E.,Peeling, J.,Janzen, A. F.
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p. 123 - 125
(2007/10/02)
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- On Organophosphorus Compounds, XXII. 1,2-Diaryl-1,2-dibromodiphosphanes
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1,2-Diaryl-1,2-dibromodiphosphanes R(Br)P-P(Br)R 2 (R = C6H5; 4-XC6H4, X = CH3O, F, Cl) were prepared by dehalogenation of RPBr2 with magnesium in a one-batch procedure.While solid 2 presumably consists of only one diastereomer there exists an equilibrium between meso-2, rac-2 and their disproportionation products RPBr2 and (RP)5 in solutions of 2.The influence of temperature, R and solvent on this equilibrium was investigated. - The reaction products of the dissolved phenyl compound 2a correspond to a reaction of its disproportionation products PhPBr2 and (PhP)5, the former preferably reacting on nucleophilic substitution, the latter with electrophilic agents.Under heterogenous conditions diphosphanes Ph(R)P-P(R)Ph can be obtained from 2a and LiR.
- Hinke, Axel,Kuchen, Wilhelm
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p. 3003 - 3010
(2007/10/02)
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