Synthesis of 5-amino-2-aminoalkyl-1,3-oxazol-4-ylphosphonic acid derivatives and their use in the preparation of phosphorylated peptidomimetics

Introduction of chiral 2-(aminoalkyl) substituents into 5-amino-1,3-oxazol-4-ylphosphonic acid derivatives and their use in phosphonodipeptide synthesis

“…We have studied the reaction of compounds 4a-c with morpholine in order to establish whether they can be cyclized to 1,3-oxazoles 26,27 containing optically active aminoalkyl 2-substituents.…”

“…24,25 A recently reported route to phosphonoglycine peptidomimetics involves the formation of 2-aminoalkyl-5-amino-1,3-oxazol-4-ylphosphonic acids followed by acid cleavage of the oxazole ring. 26,27 The method is advantageous because of easily accessible and cheap starting materials as well as for high yields and facile isolation of products in each reaction step. However, it has not hitherto been attempted in the stereoselective synthesis of acylated phosphonoglycine derivatives starting from substrates with chiral 2-(aminoalkyl) substituents on the oxazole ring.…”

The synthesis of new phosphonopeptidomimetics and their effect on the functional cardiac output

“…Ранее [9][10][11] нами было показано, что одним из перспективных методов получения фосфори-лированных пептидомиметиков является кислот-ное рас щепление 5-амино-1,3-оксазольного цикла. С целью введения в фосфонопепти дную цепь эта-нольного фрагмента нами получен диэтиловый эфир {5-[(2-гид роксиэтил)метиламино]-2-фенил-1,3-оксазол-4-ил}фосфоновой кислоты (III) из ди-этилового эфира 1-бензоиламино-2,2,2-трихлор-этилфосфоновой кислоты (I) [12] и 2-метиламино-этан-1-ола (II).…”

Synthesis of novel phosphorylated peptidomimetics which contain ω-haloalkyl and ω-thiocyanoethyl residues

“…Particular attention is drawn to the derivatives of 5-amino-1,3-oxazol-4-ylphosphonic acids, which under conditions of acidic cleavage form peptidomimetics containing the residues of phosphorylated glycine. [13][14][15][16][17][18][19] High biological activity of phosphorus-containing peptides is known. For example, selective inhibitors of cellular cymase, 20 glutathione transferase, 21,22 HCV NS3/NS4A serine protease, 23 vasoactive compounds, [24][25][26] etc., were found among these compounds.…”