%0 Journal Article
%9 ACL : Articles dans des revues avec comité de lecture répertoriées par l'AERES
%A Deng, S. L.
%A Baglin, I.
%A Nour, Mohammed
%A Cavé, C.
%T Synthesis of phosphonodipeptide conjugates of ursolic acid and their homologs
%D 2008
%L PAR00002165
%G ENG
%J Heteroatom Chemistry
%@ 1042-7163
%M CC:0002529439-0011
%N 1
%P 55-65
%R 10.1002/hc.20396
%U https://www.documentation.ird.fr/hor/PAR00002165
%V 19
%W Horizon (IRD)
%X To prepare novel derivatives of naturally bioactive 3 beta-hydroxy-urs-12-en-28-oic acid (ursolic acid) with unusual properties and broad spectrum of activities, a number of chemical reactions were conducted. First, a variety of alpha-aminophosphonates were prepared by a series of reactions involving the three-component Mannich type reaction as a key step. Second, an array of phosphonodipeptides and their homologs was synthesized through multistep reactions including condensation of phthalic anhydride with glycine or beta-alanine, chlorination of N-blocked amino acids, coupling of acid chloride with alpha-aminophosphonates and sequential hydrazinolysis. Finally, new classes of phosphonodipeptide conjugates of ursolic acid and their homologs were obtained by condensation of 3 beta-acetoxy-urs-12-en-28-oyl chloride with phosphonodipeptides and their homologs.
%$ 020 ; 076