65577-30-2Relevant academic research and scientific papers
Inhibition of the Staphylococcus aureus sortase transpeptidase SrtA by phosphinic peptidomimetics
Kruger, Ryan G.,Barkallah, Salim,Frankel, Brenda A.,McCafferty, Dewey G.
, p. 3723 - 3729 (2004)
During pathogenesis, Gram-positive bacteria utilize surface protein virulence factors such as the MSCRAMMs (microbial surface components recognizing adhesive matrix molecules) to aid the initiation and propagation of infection through adherence to host en
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.
Design, synthesis and structure-activity relationships of new phosphinate inhibitors of MurD
Strancar, Katja,Blanot, Didier,Gobec, Stanislav
, p. 343 - 348 (2007/10/03)
A series of new phosphinate compounds were designed and synthesized as inhibitors of the d-glutamic acid-adding enzyme (MurD) involved in peptidoglycan biosynthesis. They were tested against the MurD enzyme from Escherichia coli, allowing initial structure-activity relationships to be deduced. Two compounds had IC50 values near 100 μM and constitute a promising starting point for further development.
(α-aminophosphino) peptide derivatives, method for making same and therapeutic applications thereof
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, (2008/06/13)
The invention concerns compounds derived from (α-aminophosphino) peptides, of general formula (I), in which R1and R2each represents a hydrogen atom or taken together form an imine with the adjacent nitrogen atom; R3represents an alkyl group, an alkenyl group, a phenyl group, a benzyl group, all these groups capable of being substituted or not, a hydrogen atom, a cycloalkyl group, a cycloalkylmethyl group or finally, a methyl group substituted by a heterocyclic, aromatic or saturated group; R4represents a phenyl group, a benzyl group, these groups capable of being substituted or not, a hydrogen atom, an alkyl group, analkenyl group or a cycloalkyl group; R5represents an alkyl group, an alkenyl group, a phenyl group, a benzyl group, all these groups capable of being substituted or not, a hydrogen atom, a cycloalkyl, cycloalkylmethyl group or finally a methyl group substituted by a heterocyclic, aromatic or saturated group; R6, R7and R8can in particular represent a hydrogen atom, an alkyl group, a phenyl group substituted or not . . . n is equal to 0 or 1, in the form of enantiomers, diastereoisomers or racemic mixtures, their salts, their method of preparation and their therapeutic applications.
A New Synthetic Route to 1-Aminoalkylphosphonous Acids
Grobelny, Damian
, p. 942 - 943 (2007/10/02)
The addition of bis(trimethylsilyl) phosphonite to N-(diphenylmethyl)imines 1 yields bis(trimethylsilyl) 1-(diphenylmethylamino)alkylphosphonites 2, which can be easily converted into 1-(diphenylmethylamino)alkylphosphonous acids 3 by treatment with aqueo
1-Aminoalkylphosphonous Acids. Part 1. Isosteres of the Protein Amino Acids
Baylis, E. Keith,Campbell, Colin D.,Dingwall, John G.
, p. 2845 - 2853 (2007/10/02)
The synthesis of 1-aminoalkylphosphonous acids, isosteres of the protein amino acids, by addition of hypophosphorous acid to diphenylmethylimines is described.These analogues of glycine, alanine, valine, leucine, isoleucine, phenylalanine, tyrosine, tryptophan, serine, threonine, methionine, cysteine, cystine, glutamic acid, lysine, ornithine, arginine, and proline have been prepared and the analogues of alanine, valine, leucine, phenylalanine, and methionine resolved.The alanine, valine and methionine analogues have interesting antimicrobial activity and the alanine analogue has plant growth inhibiting properties.Oxidation of the appropriate 1-aminoalkylphosphonous acids gave the 1-aminoalkylphosphonic acid analogues of (+/-)-alanine, (-)-alanine, (+/-)-valine, (-)-valine, (+/-)-serine, (+/-)-threonine, (+/-)-lysine, (-)-leucine, and (+/-)-ornithine.
