80744-65-6Relevant academic research and scientific papers
Synthesis of alkyl hydrogen (1-aminoalkyl)phosphonates
Khomutov, Radii M.,Khurs, Elena N.,Osipova, Tatyana I.
experimental part, p. 106 - 107 (2011/11/14)
Addition of hypophosphorous acid to aldoximes affords (1-aminoalkyl) phosphinic acids which on treatment with bromine in alkanols are transformed into alkyl hydrogen (1-aminoalkyl)phosphonates.
Synthesis and biological evaluation of phosphino dipeptide isostere inhibitor of human β-secretase (BACE1)
Manzenrieder, Florian,Frank, Andreas O.,Huber, Timo,Dorner-Ciossek, Cornelia,Kessler, Horst
, p. 4136 - 4143 (2008/03/11)
Phosphino dipeptide (PDP) isosteres are known to be useful analogues of the transition state of metalloprotease substrates. Here we describe the use of this unit for the design of aspartic protease inhibitors. A PDP analogue of OM00-3, a potent BACE1 inhibitor, was synthesized and exhibited high biological activity (IC50 ～ 12 nM).
Facile synthesis of bis-α-aminoalkylphosphinates
Drag, Marcin,Dlugosz, Katarzyna,Oleksyszyn, Jozef
, p. 2787 - 2795 (2007/10/03)
Herein we report a facile synthesis of esters of bis-α- aminoalkylphosphinic acids obtained by an addition of Cbz-protected phosphinic analogues of amino acid methyl esters to an appropriate imine in refluxing benzene. Complete deprotection of the esters
Synthesis of α1-(Cbz-aminoalkyl)-α2- (hydroxyalkyl)phosphinic esters
Drag, Marcin,Oleksyszyn, Józef
, p. 3359 - 3362 (2007/10/03)
A synthesis of α1-(Cbz-aminoalkyl)-α2- (hydroxyalkyl)phosphinic esters was achieved by the 1,2-addition of the appropriate aldehyde to Cbz-protected phosphinic analogues of amino acid esters in the presence of at least three equivale
Synthesis of 1-Aminoalkylphosphinic Acids. Part 2. An Alkylation Approach
McCleery, Patrick P.,Tuck, Brian
, p. 1319 - 1329 (2007/10/02)
Aminomethylphosphinic acid (7), protected at nitrogen as the imine derived from benzophenone and at phosphorus as the diethylacetal and ethyl ester , undergoes facile LDA-induced alkylation.Treatment with primary alkyl halides affords, on product hydrolysis, a versatile route to phosphinic analogues of α-amino carboxylic acids.Analogues of alanine, valine, leucine, phenylalanine, tyrosine, histidine, and aspartic and glutamic acids are thus prepared; the phosphonic histidine analogue (23b) can be prepared similarly from the imine phosphonate diester (21).Intra- and inter-molecular dialkylation reactions provide analogues of 1-aminocyclopropanecarboxylic acid (14) and 2,6-diaminoheptanedioic acid (16).Benzyl bromide alkylation of (25a) and (30a), where the nitrogen is protected as the imine of the 2-hydroxypinan-3-one chiral auxiliary (24) or (29), is diastereospecific leading to asymmetric synthesis of either (+)- or (-)-phenylalanine analogues; this selectivity is compared to that shown by the corresponding chiral imine phosphonate (25b) and imine carboxylate (25c).
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.
