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88. Nalkylated 3,5bisarylidene4piperidones. Synthetic approaches, Xray structure and anticancer activity

Author

Makarov, Michael V., Odinets, Irina L., Lyssenko, Konstantin A., Rybalkina, Ekaterina Yu., Kosilkin, Ilya V., Antipin, Mikhail Yu., and Timofeeva, Tatiana V.

Abstract

In a search for cytotoxic fluorescent materials a series of Nalkylated and N,Ndialkylated 3,5bisarylidenepiperidones was synthesized. Alkylation of 3,5bisarylidene4piperidone afforded quaternary salts only while condensation of Nalkyl4piperidones with substituted benzaldehydes was a convenient route to the corresponding Nalkylated compounds. Compounds and their pharmaceutically acceptable salts demonstrated high activity against resistant human lung carcinoma cell line A549 with IC50values in the range of 0.36.5 μM.

Published
2008
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89. The Phosphorus Aspects of Green Chemistry: the Use of Quaternary Phosphonium Salts and 1,3-Dialkylimidazolium Hexafluorophosphates in Organic Synthesis

Author

Keglevich, Gyorgy, Baan, Zoltan, Hermecz, Istvan, Novak, Tibor, and Odinets, Irina L.

Abstract

The search for suitable ionic liquids that are non-volatile, non-toxic, dissolve a variety of reactants and are recyclable is a real challenge for chemists to be able to replace the traditional solvents that are volatile, flammable and toxic. This segment of chemistry has, these days, become a firm part of green chemistry attracting much attention. The present review summarizes and critically discusses the data accumulated in recent years on the synthesis and utilization of phosphorus containing ionic liquids, such as imidazolium hexafluorophosphates and phosphonium salts. As regards the preparation of ionic liquids, the key steps are quaternization and the introduction of the corresponding anion. Physical properties of the ionic liquids can be fine-tuned by selecting suitable cation-anion pairs. The reactions studied in ionic liquids embraces catalytic hydrogenations, transfer hydrogenations, oxidations, hydroformylations, carbonylations, alkylations, acylations, nucleophilic substitutions, halogenations, condensations, Diels-Alder reactions, Michael additions, coupling reactions and transformations in organophosphorus chemistry. Ionic liquids are especially suitable to accommodate catalytic reactions where one of the components is a gas. Stress was laid to highlight the chemo-, regio-, diastereo- and, especially, the enantioselectivity of the reactions performed in ionic liquids. The data on the ecotoxicity of imidazolium hexafluorophosphates and phosphonium salts are briefly discussed.

Published
2007

90. Synthesis and Coordination Chemistry of Cyano-Substituted Phosphines

Author

Odinets, Irina L., Vinogradova, Natalya M., Matveeva, Ekaterina V., and Mastryukova, Tatyana A.

Abstract

Synthetic approaches to both linear and cyclic cyano-substituted phosphines (P∼CN-phosphines) found an industrial application as catalyst precursors, pesticides, herbicides, flame retardants, precursors of aminophosphines etc., are reported. The main synthetic routes include reduction of P=O containing precursors, alkylation of silylphosphines and metal phosphides by halogenoalkyl(aryl)carbonitriles, phosphorylation of the latter ones, decomposition of phosphonium salts and hydrophosphination of cyano-substituted olefins proceeding under non-catalytical conditions and with use of metal complex catalysis. Merits and demerits of each approach are discussed. Phosphines bearing cyano function as an additional coordination site show diverse coordination behavior depending on the phosphine structure and nature of the metal. Four main types of complexes are observed, namely those with P-monodentate coordination, with N-monodentate coordination and complexes where bidentate coordination mode of P and N atoms is realized either at the single metal atom or of bridged type between two different metal atoms. Thus coordination behavior of such P∼CN-ligands relative to transition and non-transition metals, structure features of the complexes obtained and their application in catalytic processes are discussed.

Published
2005

91. Complexation of (1-diphenylphosphino)cyclopropanecarbonitrile with palladium(II)

Author

Vinogradova, Natalya M., Odinets, Irina L., Lyssenko, Konstantin A., Pasechnik, Margarita P., Petrovskii, Pavel V., and Mastryukova, Tatyana A.

Abstract

(1-Diphenylphosphino)cyclopropanecarbonitrile 1 was synthesised by the reduction of a phosphine oxide; the interaction of 1 with (PhCN)2PdCl2 leads to 1:1 or 1:2 complexes depending on the ratio between the reactants.

Published
2001

98. A monoclinic polymorph of α-diphenyl­phosphor­yl- o-cresol.

Author

Nelubina, Yulya V., Alexanyan, Diana V., Kozlov, Vladimir A., Lyssenko, Konstantin A., and Odinets, Irina L.

Subjects
*DIBENZOYLMETHANE, *PHOSPHORYLASES, *CRYSTALS spectra, *CRYSTALLOGRAPHY, *MAGNETIC structure, *MOLECULAR structure, *CHEMICAL bonds, *CHEMICAL structure, *MOLECULAR association
Abstract

When attempting the synthesis of the copper complex of the title compound {systematic name: 2-[(diphenyl­phosphor­yl)­meth­yl]phenol}, C19H17O2P, a new monoclinic polymorphic modification of the ligand was obtained instead of the complex. The variations of mol­ecular geometry and supramol­ecular organization in the crystal structures of the two polymorphs are discussed. [ABSTRACT FROM AUTHOR]

Published
2005
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99. Synthesis of functionalized bisphosphonates via click chemistry.

Author

Skarpos H, Osipov SN, Vorob'eva DV, Odinets IL, Lork E, and Röschenthaler GV

Subjects
Alkynes chemistry, Diphosphonates chemical synthesis, Models, Molecular, Molecular Structure, Diphosphonates chemistry
Abstract

An efficient general synthetic approach giving the possibility for facile, rapid and cheap access to a wide range of novel nitrogen-bisphosphonates (N-BPs) as potent drug candidates, based on the reaction of mono- and bis-propargyl-substituted bisphosphonates with a variety of azides under Cu(i) catalysis ("click" methodology), has been developed. The method allows the incorporation of two functionalities into the N-BP molecule simultaneously, as well as to ligate in situ two N-BPs to one another via the one-pot reaction of organic dibromides with propargyl-substituted bisphosphonates, generating both the diazide and Cu(I) moieties.

Published
2007
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100. Methyltrifluoropyruvate imines possessing N-oxalyl and N-phosphonoformyl groups--precursors to a variety of alpha-CF3-alpha-amino acid derivatives.

Author

Skarpos H, Vorob'eva DV, Osipov SN, Odinets IL, Breuer E, and Röschenthaler GV

Subjects
Amino Acids chemistry, Electrons, Amino Acids chemical synthesis, Imines chemistry, Pyruvic Acid analogs & derivatives, Pyruvic Acid chemistry
Abstract

Convenient routes to methyl 2-oxalylimino- and 2-(phosphonoformimido)-3,3,3-trifluoropropanoates have been elaborated, based on the reaction of methyl trifluoropyruvate with ethyl oxamate or diethyl carbamoylphosphonate, respectively, followed by dehydration. The compounds obtained are useful synthetic intermediates toward a variety of novel 3,3,3-trifluoroalanine derivatives that are potential drug candidates.

Published
2006
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