RESUMEN
The method for the synthesis of 2-substituted 2-hydroxycarbonylethyl-1-aminoalkylphosphinic acids (I) (pseudo-alpha,alpha-dipeptides) from ammonium and potassium hypophosphites (II) is described. The proposed route to the synthesis of pseudo-alpha,alpha-dipeptides consists in addition hypophosphite to acrylic compounds and formation of the first phosphorus-carbon bond with following addition of aminoacid fragment and formation of the second phosphorus-carbon bond. The key intermediates of the synthesis - phosphonous acids (III) and their silylic esters (IV) were obtained at the first stage of the process as the result of the addition of the bis(trimethylsilyl)hypophosphite in situ to suitably substituted acrylates. The modificated procedure for the Kabachnik-Fields reaction of 2-substituted 2-alkoxycarbonylethyl phosphonous acids (III), acetamide, benzaldehyde in acetic anhydride with following hydrolysis results in 2-substituted 2-hydroxycarbonylethyl-alpha-aminobenzyl phosphinic acids (Ia-c) (pseudo-phenylglycylpeptides). Bis(trimethylsilyl) 2-substituted 2-alkoxycarbonylethylphosphonites (IV) in situ were added to N-tritylmethanimine and following alcoholysis and acid hydrolysis of addition products gave 2-substituted 2-hydroxycarbonylethyl-aminomethylphosphinic acids (Id-f) (pseudo-glycylpeptides).
Asunto(s)
Dipéptidos/síntesis química , Ácidos Fosfínicos/síntesis químicaAsunto(s)
Agrostemma/efectos de los fármacos , Citocininas/farmacología , Regulación de la Expresión Génica de las Plantas/efectos de los fármacos , Nitrato Reductasas/metabolismo , Nitratos/farmacología , Semillas/efectos de los fármacos , Agrostemma/embriología , Agrostemma/enzimología , Nitrato Reductasas/genética , Reguladores del Crecimiento de las Plantas/farmacología , ARN Mensajero/metabolismoAsunto(s)
Mesembryanthemum/metabolismo , Fotosíntesis/fisiología , Adaptación Fisiológica/fisiología , Concentración de Iones de Hidrógeno , Fosfoenolpiruvato Carboxilasa/genética , Fosfoenolpiruvato Carboxilasa/metabolismo , Fenómenos Fisiológicos de las Plantas , Cloruro de Sodio/metabolismo , Factores de Tiempo , Transcripción Genética/efectos de los fármacosAsunto(s)
Hipocampo/efectos de los fármacos , Neuronas/efectos de los fármacos , Receptores de N-Metil-D-Aspartato/antagonistas & inhibidores , 2-Amino-5-fosfonovalerato/farmacología , Potenciales de Acción , Aminoácidos/farmacología , Animales , Anticonvulsivantes/farmacología , Conducta Animal/efectos de los fármacos , Hipocampo/citología , Ratones , N-Metilaspartato/farmacología , Neuronas/fisiología , Ratas , Especificidad de la EspecieRESUMEN
The action of a series of phosphonic amino acids--glutamate receptor antagonists--on neuromuscular transmission in blowfly larva was studied under voltage clamp conditions. It was shown that 2-amino-4-phosphonobutyric acid decreases synaptic current in a dose-dependent manner, and 2-amino-7-phosphonoheptanoic acid increases its acting presynaptically. The analysis done shows that sensitivity of blowfly glutamate receptors to phosphonic amino acids differs from that in crustacean and mammalian glutamate receptors.
