Synthesis and bioactivity of fluorine compounds containing isoxazolylamino and phosphonate groups

Song, Baoan; Yang, Song; Hong, Yanping; Zhang, Guoping; Jin, Linhong; Hu, Deyu

doi:10.1016/j.jfluchem.2005.08.005

Cited by 41 publications

(15 citation statements)

References 21 publications

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“…31 P{ 1 H}NMR spectra were recorded on a Varian Inova 500 MHz spectrometer at room temperature with DMSO-d 6 as a solvent and TMS as an internal standard and 85% H 3 PO 4 as an external reference, respectively. Elemental microanalyses were performed at the microanalysis center in Bulgarian Academy of Science, Sofia, Bulgaria.…”

Section: Methodsmentioning

confidence: 99%

Synthetic approach for novel bis(α‐aminophosphonic acid) derivatives of chromone containing 1,2,4,3‐triazaphosphole moieties

Ali

Halacheva

2009

Heteroatom Chemistry

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Section: Methodsmentioning

confidence: 99%

Synthetic approach for novel bis(α‐aminophosphonic acid) derivatives of chromone containing 1,2,4,3‐triazaphosphole moieties

Ali

Halacheva

2009

Heteroatom Chemistry

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“…Thus anodic fluorination of a-phenylsulfanyl-substituted cyclic diketone 10 results in monofluoro derivative 11 in a yield of 46%. 42 In the case of a-phenylsulfanylacetylacetone 12, the corresponding monofluoro-1,3-diketone could not be obtained; under these conditions, elimination of the acetyl group occurred to form 1-fluoro-1-phenylsulfanylpropan-2-one (13). 42 Selective electrochemical a-monofluorination of indan-1,3-dione (14) requires potentiostatic conditions.…”

Section: Reagentmentioning

confidence: 99%

Chemistry of fluoro-substituted β-diketones and their derivatives

Isakova¹,

Хлебникова²,

Лахвич³

2010

Russ. Chem. Rev.

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“…Typically, a-aminoalkanephosphonates are formed in good yield by treating a carbonyl compound and an amine with a dialkyl phosphite in the presence of an organic base, an alkali metal alkoxide, or a Brønsted/Lewis acid. Recent preparative modifications of the reaction which significantly simplify the original method and increase the yield of the product concern the use of microwave irradiation [44][45][46][47][48][49], silica gel-supported reagents [43,46,49,50], surface-mediated reactions on Al 2 O 3 [51,52], ionic liquids as solvents [53], solvent-free conditions [43,44,47,54,55], and water-tolerant catalysts (magnesium perchlorate [56,57], lithium perchlorate [58,59], metal triflates [60][61][62], indium trichloride [63], samarium diiodide [64], lanthanide trichloride [65], TaCl 5 /SiO 2 [66], bismuth nitrate pentahydrate [67], scandium tris (dodecyl sulfate) [68], tetrabromomethane [54], and montmorillonite KSF [69]). …”

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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Synthesis and bioactivity of fluorine compounds containing isoxazolylamino and phosphonate groups

Cited by 41 publications

References 21 publications

Synthetic approach for novel bis(α‐aminophosphonic acid) derivatives of chromone containing 1,2,4,3‐triazaphosphole moieties

Synthetic approach for novel bis(α‐aminophosphonic acid) derivatives of chromone containing 1,2,4,3‐triazaphosphole moieties

Chemistry of fluoro-substituted β-diketones and their derivatives

Chemistry of Aminophosphonic Acids and Phosphonopeptides

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