6324-00-1Relevant academic research and scientific papers
Phosphonic acid analogs of fluorophenylalanines as inhibitors of human and porcine aminopeptidases N: Validation of the importance of the substitution of the aromatic ring
Dziuk, B?a?ej,Kafarski, Pawe?,Pirat, Jean-Luc,Talma, Micha?,Wanat, Weronika
, (2020/05/04)
A library of phosphonic acid analogs of phenylalanine substituted with fluorine, chlorine and trifluoromethyl moieties on the aromatic ring was synthesized and evaluated for inhibitory activity against human (hAPN) and porcine (pAPN) aminopeptidases. Fluorogenic screening indicated that these analogs are micromolar or submicromolar inhibitors, both enzymes being more active against hAPN. In order to better understand the mode of the action of the most active compounds, molecular modeling was used. It confirmed that aminophosphonic portion of the enzyme is bound nearly identically in the case of all the studied compounds, whereas the difference in activity results from the placement of aromatic side chain of an inhibitor. Interestingly, both enantiomers of the individual compounds are usually bound quite similarly.
1-(N-Acylamino)alkylphosphonic acids—Deacylation in aqueous solutions
Cypryk, Marek,Drabowicz, Jozef,Gostynski, Bartlomiej,Kudzin, Marcin H.,Kudzin, Zbigniew H.,Urbaniak, Pawel
, p. 651 - 658 (2017/06/05)
The 1-(N-acylamino)alkylphosphonic acids (AC)-AAP belong to the interesting and potentially of pharmacological importance group of 1-aminoalkylphosphonic acids derivatives. Since susceptibility of (AC)-AAP on hydrolytic deacylation can form important factor influencing their biological activity, we have undertaken deacylation investigations of these compounds in aqueous media. In this article, we present our results on deacylation of various types of 1-(N-acylamino)alkylphosphonic acids (AC)-AAP, including 1-(N-acetylamino)alkyl-phosphonic Ac-AAP, 1-(N-chloroacetylamino)alkylphosphonic acids Mca-AAP, 1-(N-trifluoroacetylamino)alkylphosphonic acids TFA-AAP, and 1-(N-benzoylamino)-alkylphosphonic Bz-AAP, derived from representative 1-aminoalkylphosphonic acids AAP (GlyP, AlaP, ValP, PglP, and PheP) in neutral and 2?M HCl solutions.
A (E) - 2-aryl ethylene cinnamenyl method for preparing ester derivative
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Paragraph 0042-0045, (2017/03/08)
The invention discloses method for preparing (E)-2-aryl vinyl phosphonate derivatives. The method comprises the specific following steps of dissolving 1-nitro-2-aryl-vinyl derivatives, a phosphorus reagent, an accelerator manganese acetate and a catalyst copper acetate in a solvent and reacting at 20-100 DEG C to obtain the (E)-2-aryl vinyl phosphonate derivatives. According to the method disclosed by the invention, the 1-nitro-2-aryl-vinyl derivatives are adopted as starting materials, the raw materials are easily available and have multiple varieties; the products obtained by the method disclosed by the invention are multiple and can be directly applied and can be also used for other further reaction; according to the method, the use of precious metal reagents and other additives is avoided; and meanwhile, the synthetic route is short, reaction conditions are mild, the reaction operation and post-treatment process are simple, the yield is high and the method is suitable for scale production.
Synthesis of phosphinic and phosphonic analogs of aromatic amino acids
Belyankin,Khomutov,Zhukov,Kartasheva,Khomutov
, p. 133 - 136 (2007/10/03)
The reaction of aryl and aralkyl aldoximes with hypophosphorous acid resulted in aminophosphinic acids, which were oxidized into the corresponding aminophosphonic acids.
A simple synthesis of 1-aminophosphonic acids from 1-hydroxyiminophosphonates with NaBH4 in the presence of transition metal compounds
Demir, Ayhan S.,Tanyeli, Cihangir,Sesenoglu, Oezge,Demic, Serafettin,Evin, Oezden Oezel
, p. 407 - 410 (2007/10/02)
A new procedure has been developed for the synthesis of 1-aminophosphonic acids. Diethyl phosphonates are converted to hydroxyiminophosphonates when treated with hydroxylamine hydrochloride. Reduction of hydroiminophosphonates with NaBH4 in MeOH in the presence of MoO3 or NiCl2 and hydrolysis of 1-aminophosphonates gave 1-aminophosphonic acids in good yields.
The synthesis of 1-aminobenzylphosphonic acids from benzylidenediphenylmethylamines, for use as structural units in antithrombotic tripeptides
Green, Donovan,Patel, Geeta,Elgendy, Said,Baban, Jehan A.,Claeson, Goran,Kakkar, Vijay V.,Deadman, John
, p. 5099 - 5108 (2007/10/02)
Acid hydrolyses of O,O-dimethyl or O,O-diethyl 1-(diphenylmethylamino) benzylphosphonate intermediates 2, formed from the addition at elevated temperature of dimethyl or diethyl phosphite to benzylidenediphenylmethylamines 1, generates 1-aminobenzylphosphonic acids 3 in good yield.
Preparation of optically active 1-aminoalkylphosphonic acids by stereoselective enzymatic hydrolysis of racemic N-acylated 1-aminoalkylphosphonic acids
Solodenko,Kasheva,Kukhar,Kozlova,Mironenko,Svedas,Belozersky
, p. 3989 - 3998 (2007/10/02)
N-Phenylacetylated derivatives of 1-aminoalkylphosphonic acids were synthesized and high enantioselectivity of their hydrolysis by penicillin acylase (EC 3.5.1.11) was demonstrated. Stereoselective enzymatic hydrolysis of racemic 1-(N-phenylacetylamino) alkylphosphonic acids was used for preparation of enantiomeric 1-aminoalkylphosphonic acids. The kinetic regularities of penicillin acylase catalyzed hydrolysis were established and the biocatalytic process was optimized to increase the optical purity and the yield of the optically active product.
ORGANIC PHOSPHORUS COMPOUNDS 91. SYNTHESIS AND PROPERTIES OF 1-AMINO-2-ARYLETHYLPHOSPHONIC AND -PHOSPHINIC ACIDS AS WELL AS -PHOSPHINE OXIDES
Maier, Ludwig
, p. 43 - 67 (2007/10/02)
The preparation, physical and spectroscopic properties of 1-amino-2-arylethylphosphonic, and -phosphinic acids as well as -phosphine oxides, the phosphorus analogues of phenylalanine are described, and the reactions of 1-amino-2-(4-fluorophenyl)ethylphosphonates with acetals, isocyanides, esters, acid anhydrides, activated aromatic nitro- and halogen compounds, and with N-protected alanine are reported.It is shown that several of the 1-amino-2-arylethylphosphonic acids are strong inhibitors of PAL and anthocyanin synthesis and also are quite active botryticides.Among the active compounds were 1-amino-2-(4-fluorophenyl)ethylphosphonic acid, 3f, and the methyl-substituted compounds 3k, 3l, and 3m.The fluoroderivative 3f was also effective as a seed-dressing agent in barley showing a 100percent protection against the fungus Fusarium nivale at 600 ppm.
SYNTHESIS OF NEW PHOSPHONATE INHIBITORS OF SERINE PROTEASES
Fastrez, Jacques,Jespers, Laurent,Lison, Dominique,Renard, Michel,Sonveaux, Etienne
, p. 6861 - 6864 (2007/10/02)
Analogues of phenylalanine and lysine esters were synthesized, and their inhibitory power tested in vitro respectively on chymotrypsin, trypsin and urokinase.
1-Aminoalkanephosphonic acids. Addition of diethyl phosphite to N-diisobutylaluminio-aldimines
Kudzin, Zbigniew H.,Majchrzak, Michal W.
, p. 245 - 248 (2007/10/02)
A new route to 1-aminoalkanephosphonic acids starting from nitriles has been elaborated.The nitriles are reduced by Dibal-H into imine derivatives; addition with diethyl phosphite gives the corresponding 1-aminoalkanephosphonates.Hydrolysis of latter compounds gives the 1-aminoalkanephosphonic acids.
