Lipophilic aminophosphonates and their calix[4]arene derivatives: synthesis and membrane transport of biorelevant species

Стойков, И. И.; Repejkov, Sergej A.; Антипин, И. С.; Коновалов, А. И.

doi:10.1002/1098-1071(2000)11:7<518::aid-hc10>3.3.co;2-r

Cited by 3 publications

(3 citation statements)

References 4 publications

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“…It was shown earlier that calix[4]arenes containing aminophosphonate fragments on the upper rim of molecule are effective and selective amino acid transfer agents compared with their linear counterparts and lipophilic derivatives of aminophosphine oxides participate both in membrane transport of amino acids and as metal ion extractants from acidic media . It is anticipated that the presence of lipophilic cavity with a long alkyl chain and four thermally and hydrolytically stable aminophosphine oxide fragments in synthesized calix[4]resorcinol would increase the binding efficiency and selectivity with organic and inorganic substrates compared with their linear counterparts and unsubstituted calix[4]resorcinol.…”

Section: Resultsmentioning

confidence: 99%

Phosphorylated Aminoacetal in the Synthesis of New Acyclic, Cyclic, and Heterocyclic Polyphenol Structures

Vagapova

Бурилов

Voronina

et al. 2014

Heteroatom Chemistry

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New phosphorylated aminoacetal has been synthesized by the Kabachnik–Fields reaction; its reactivity has been studied in acid‐catalyzed condensation with linear polyphenols (2‐methylresorcinol, resorcinol, pyrogallol) and the Mannich reaction with macrocyclic polyphenol (calix[4]resorcinol). It has been determined for the first time that acid‐catalyzed reaction of phosphorus‐containing acetal with resorcinol and its derivatives in ethanol in the presence of hydrochloric acid gives new phosphorylated piperazines in addition to the compounds of diarylmethane series. Condensation of macrocyclic polyphenol (calix[4]resorcinol) with formaldehyde and N‐((dihexylphosphoryl)methyl)‐2, 2‐dimethoxyethylamine (the Mannich reaction) has resulted in novel tetrasubstituted calixarene containing aminophosphine oxide and acetal groups on the “upper rim” of molecule.

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Section: Resultsmentioning

confidence: 99%

Phosphorylated Aminoacetal in the Synthesis of New Acyclic, Cyclic, and Heterocyclic Polyphenol Structures

Vagapova

Бурилов

Voronina

et al. 2014

Heteroatom Chemistry

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“…For further details of this subject, readers are referred to the leading references cited in a monograph [27] and reviews [41,42]. In recent years, many new cyclic a-aminophosphonic acids have been prepared, such as a-aminocyclopropylphosphonic acids, as well as their cyclobutyl, cyclopentyl, and cyclohexyl analogs 13 [60,[79][80][81][82]. 4-Heterocyclohexyl phosphonates 14 and 3-heterocyclohexylphosphonates 15 were efficiently prepared from heterocyclic ketones via phosphite addition to iminium ions formed by in situ condensation of these ketones with benzylic amines [83].…”

Section: Amidoalkylation In the Carbonyl Compound-amine-phosphite Thrmentioning

confidence: 99%

Chemistry of Aminophosphonic Acids and Phosphonopeptides

Kukhar

Romanenko

2009

Amino Acids, Peptides and Proteins in Organic Chemistry

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Aminophosphonic (and aminophosphinic) acids occupy a prominent position in the understanding of bioprocesses in living organisms and in the construction of new bioregulators -pharmaceuticals and agrochemicals. The so-called phosphorus analogs of the amino acids, aminophosphonic and aminophosphinic acids, are amino acid mimetics in which the carboxylic group is substituted by a phosphonic acid residue P(O)(OH) 2 or phosphinic acid group P(O)(OH)R. The replacement of the carboxylic group by a phosphonic or related moiety results in a number of important consequences: the central atom of a phosphonic acid function consists of an additional substituent that has a tetrahedral configuration in contrast to the planar carbonyl atom of carboxylic group. There are also significant differences in the acidity and steric bulk of these residues. The tetrahedral configuration of the pentavalent phosphorus atom mimics the transition state of the peptide bond cleavage reaction in some enzyme-substrate interactions that is used in the synthesis of new inhibitors. The hydrolytic stability of CÀP bonds is often used in order to prepare stable analogs of bioactive phosphates OÀP(O)(OH) 2 . In addition, aminophosphonic acids and their derivatives are important as metal-complexing agents, which have diagnostic and therapeutic applications, and as industrial chemicals in water treatment, metal extraction, or pollution control.Synthesis, and the chemical, physical, and biological properties of aminophosphonic acids and some directions for their practical application are presented in a number of reviews and book chapters. The most comprehensive account of the chemistry and biology of aminophosphonates and aminophosphinate which covers literature up to 2000 is presented in Kukhar and Hudson ([1] and references therein). Readers are referred to this reference for more detailed information concerning specific aspects of the chemistry and biological activity of aminophosphonic acid derivatives. The purpose of this chapter is to give an updated report on aminophosphonic acids as analogs of amino acids. Numerous heterocyclic compounds that contain both phosphonic and amino groups will not be covered in this report.

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“…In the head row of the table, we also give the pK a values [9] and the log octanol3water partition coefficients (log P) [10] characterizing the hydrophilicity of the compounds.…”

Section: äääääääääääämentioning

confidence: 99%

Choline Esterase Inhibitors and Synthetic Oxalic Acid Receptors Based on Calix[4]arene Derivatives

et al. 2005

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New reversible butyrylcholine esterase inhibitors based on calix[4]arene derivatives were suggested. A series of new distally disubstituted calix [4]arenes were prepared in 60 380% yields. Some of these compounds showed properties of reversible choline esterase effectors, activating it at low concentrations and inhibiting at high concentrations. The macrocycles prepared were tested in extraction of d,l-tartaric, glycolic, d,l-mandelic, d,l-glutamic, malonic, oxalic, and succinic acids and of sodium acetate. Oxalic acid is efficiently transferred through a liquid impregnated membrane under the action of calix[4]arenes with nitrogen-containing substituents.Various biochemical processes such as recognition, reaction, active and selective transport, and reception [1] are based on intermolecular interactions. Transformation of the genetic information into such cell functions as growth activation and regulation of enzymes [1] is based on recognition and selective binding of the protein surface with biopolymers. Active studies made in the past decade are aimed at development of synthetic small molecules whose target is protein3 protein interaction [2, 3].Relatively simple and synthetically accessible molecules capable to reversibly [switch] various functions of proteins are interesting as potential components of drugs enhancing the specificity of the active component and its selective transport in patient's body [4]. However, the high degree of solvation and large area of the protein surface complicate the designing of molecules capable to reversibly alter the protein function. Calixarenes, being low-toxic and containing several functionalization centers, show promise for development of new highly effective drugs.We have shown recently that some distally substituted calix[4]arenes inhibit the hydrolysis of indophenyl acetate with butyrylcholine esterase, which is due to formation of host3guest complexes of calixarene with indophenyl acetate and localization of the resulting supramolecule near the active center of the enzyme [3].To examine the influence of structural factors on the interaction of calix[4]arenes with a model protein, butyrylcholine esterase, we prepared a series of new 1,3-disubstituted (at the lower rim) p-tert-butylcalix-[4]arenes containing proton-donor (I), proton-acceptor (II), and electron-acceptor (III, IV) groups. Dicarboxylic acid I was prepared by hydrolysis of the corresponding ester. Compounds II3IV were prepared by selective alkylation of p-tert-butylcalix [4]arene with the corresponding halo derivatives in acetonitrile in the presence of potassium carbonate.

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Lipophilic aminophosphonates and their calix[4]arene derivatives: synthesis and membrane transport of biorelevant species

Cited by 3 publications

References 4 publications

Phosphorylated Aminoacetal in the Synthesis of New Acyclic, Cyclic, and Heterocyclic Polyphenol Structures

Phosphorylated Aminoacetal in the Synthesis of New Acyclic, Cyclic, and Heterocyclic Polyphenol Structures

Chemistry of Aminophosphonic Acids and Phosphonopeptides

Choline Esterase Inhibitors and Synthetic Oxalic Acid Receptors Based on Calix[4]arene Derivatives

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