108327-37-3Relevant articles and documents
Novel methodology for the solid-phase synthesis of phosphinic peptides
Buchardt, Jens,Meldal, Morten
, p. 3306 - 3310 (2000)
A novel, versatile strategy for the solid phase synthesis of phosphinic peptides is developed in which the phosphorus-carbon bond is formed on a polymer support during peptide synthesis. The formation of bis(trimethylsilyl) 1-(allyloxycarbonylamino)ethylphosphonite from 1-(allyloxycarbonylamino)ethylphosphinic acid is investigated, as well as the Michael addition of the former to a resin-bound acrylate. Conditions are also established for the clean, quantitative conversion of a resin-bound, N-terminus acryloylated peptide with bis(trimethylsilyl) 1-(allyloxycarbonylamino)-ethylphosphonite. Conventional peptide synthesis is then employed to obtain a phosphinic undecapeptide in high yield and purity.
AMINOPHOSPHINIC DERIVATIVES THAT CAN BE USED IN THE TREATMENT OF PAIN
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Page/Page column 9, (2011/06/19)
The present invention relates to a compound of the following general formula (I): R1—NH—CH(R2)—P(═O)(OR3)—CH2—C(R4)(R5)—CONH—CH(R6)—COOR7 (I) or a pharmaceutically acceptable salt of the latter, an isomer or a mixture of isomers in any proportions, especially a mixture of enantiomers, and in particular a racemic mixture, for which R1 represents a —C(═O)—O—C(R8)(R9)—OC(═O)—R10 group; R2 represents an optionally substituted hydrocarbon-based chain, an aryl or heteroaryl group or a methylene group substituted by a heterocycle; R3 represents a hydrogen atom or a —C(R12)(R13)—OC(═O)—R14 group; R4 and R5 form, together with the carbon that bears them, a saturated hydrocarbon-based ring or an optionally substituted piperidine ring or R4 represents a hydrogen atom and R5 represents a phenyl or a benzyl that is optionally substituted, a heteroaromatic ring or a methylene group substituted by a heterocycle; R6 represents an optionally substituted hydrocarbon-based chain or a phenyl or a benzyl that is optionally substituted; and R7 represents a hydrogen atom or a benzyl, alkyl, heteroaryl, alkylheteroaryl, —CHMe—COOR18, —CHR19—OC(═O)OR20 and —CHR19—OC(═O)OR20 group. The present invention also relates to the use of these compounds as a medicinal product, and in particular for the treatment of pain, more advantageously neuropathic and neuroinflammatory pain, to their method of synthesis and also to the compositions containing them.
Phosphinate, sulfonate, and sulfonamidate dipeptides as potential inhibitors of Escherichia coli aminopeptidase N
Yang, Ke-Wu,Golich, Frank C.,Sigdel, Tara K.,Crowder, Michael W.
, p. 5150 - 5153 (2007/10/03)
In an effort to prepare novel inhibitors of bacterial aminopeptidase N (PepN), the phosphinate, propenylphosphinate, decylphosphinate, sulfonate, and sulfonamidate analogs of Ala-Ala were synthesized and tested as inhibitors. Phosphinate 1 was shown to inhibit PepN with a Ki of 10 μM, and propenylphosphinate 2 and decylphosphinate 3 inhibited PepN with a Ki of ca. 1 μM. Sulfonate and sulfonamidate analogs did not inhibit PepN.
