Biological Activity of Aminophosphonic Acids

Kafarski, Paweł; Lejczak, Barbara

doi:10.1080/10426509108029443

Cited by 978 publications

(343 citation statements)

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“…However, attempts on their degradation, carried out by Birum for Cm-AA P (OPh) 2 and/or Cm-[AA P (OPh) 2 ] 2 , revealed low to moderate stability of the ester functions and higher stability at applied conditions of the amide function (Scheme 3). In the Birum condensation, which formally can be considered as a variant of the Arbuzov reaction, and also as a type of the amidoalkylation of phosphorus(III) esters, the key electrophilic reagent prepared in situ from an amide substrate and an aldehyde, adds to the corresponding phosphite (phosphonite, phosphinite) afford the variety of structurally diverse P-C-N products (Scheme 4, Table 1).…”

Section: Methods Based On Additions Of the P-h Functions To Multiple mentioning

confidence: 99%

“…Compound Ptc-AA P (OPh) 2 (0.005 mol) is dissolved in a mixture of glacial acetic acid (1 ml) and hydrochloric acid (36 %, 10 ml) and heated under reflux for 7 h. The solvents are evaporated under reduced pressure and the residue is dissolved in ethanol (20 ml). The ethanolic solution of the amino acid hydrohalide is treated with methyloxirane until pH 6 is reached.…”

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confidence: 99%

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Thioureidoalkylphosphonates in the synthesis of 1-aminoalkylphosphonic acids. The Ptc-aminophosphonate method

Kudzin¹,

Kudzin²,

Drabowicz³

2011

Arkivoc

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1-Aminoalkylphosphonic acids (AA P ) as structural analogues of protein amino acids (AA C ), are important inhibitors of amino acids metabolism. One of the three methods which have contributed to the development of the chemistry of 1-aminoalkylphosphonic acids is the Ptcaminoalkylphosphonate (Phenylthiocarbamoylaminoalkylphosphonate) method which allows a time saving synthesis of structurally diverse AA P of analytical purity on mmol-mol scale This review presents a comprehensive survey of this methodology development, with an emphasis on its scope and limitations.

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Section: Methods Based On Additions Of the P-h Functions To Multiple mentioning

confidence: 99%

mentioning

confidence: 99%

Thioureidoalkylphosphonates in the synthesis of 1-aminoalkylphosphonic acids. The Ptc-aminophosphonate method

Kudzin¹,

Kudzin²,

Drabowicz³

2011

Arkivoc

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“…aryl-and vinyl-phosphonates, phosphine oxides and related derivatives) are compounds of practical importance in industry, agriculture, and medicine as well as in everyday life [34][35][36][37][38][39]. In addition to their applications as pesticides, detergents, or anticorrosive agents, these phosphorus-containing synthetic compounds Scheme 10 Pd/C-catalyzed synthesis of aryl diphenylphosphine oxides (28) in water Scheme 11 Ligand-free synthesis of arylphosphonates/phosphine oxides (30) have received a lot of attention both in drug research and in medicinal chemistry due to their great potential in combating diseases and pathological conditions, and curing parasitic infections [40].…”

Section: Applications Of the Hirao Productsmentioning

confidence: 99%

Microwave-assisted Hirao reaction: recent developments

Brahmachari

2015

ChemTexts

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Organic molecules containing phosphorus, now, constitute a major branch of chemistry, and offer fascinating possibilities for their structural, synthetic, and mechanistic study as well as promising biological activities. Organophosphorus compounds find numerous potential applications in the areas of industrial, agricultural, and medicinal chemistry. Aryl-and vinyl-phosphonates are an important class of organophosphorus compounds with potential biological relevance. The Hirao reaction offers a way to access these compounds through phosphorus-carbon (P-C) cross-coupling of aryl and vinyl halides with O,O-dialkyl phosphites, and this reaction has attained a commendable development in many ways in regard to the diversity in the substrates, [P(O)H species, catalysts, and reaction conditions. The present article deals with such developments that occurred under the influence of microwave irradiation.

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“…These features explain the large range of biological activities displayed by the members of this important class of compounds and the applications. [2][3][4][5] They have been found in areas ranging from medicine to agriculture, for example, as antibiotics, 6 enzyme inhibitors, 7 anticancer agents 8 and herbicides. 9,10 These biological properties mostly are associated with the tetrahedral structure of the phosphonyl group acting as a "transition-state" analogue.…”

Section: Introductionmentioning

confidence: 99%