Synthesis of dehydroepiandrosterone analogues modified with phosphatidic acid moiety

Dehydroepiandrosterone (DHEA) and its metabolite 7α-OH DHEA have many diverse physiological, biological and biochemical effects encompassing various cell types, tissues and organs. In in vitro studies, DHEA analogues have myriad biological actions, but in vivo, especially in oral administration, DHEA produces far more limited clinical effects. One of the possible solutions of this problem is conversion of DHEA to active analogues and/or its transformation into prodrug form. In this article, the studies on the conversion of DHEA and 7α-OH DHEA into their phosphatides by the phosphodiester approach are described. In this esterification, N,N-dicyclohexylcarbodiimide (DCC) was the most efficient coupling agent as well as p-toluenesulphonyl chloride (TsCl).

Research highlights▶ Conversion of DHEA and 7α-OH DHEA into their phosphatides by the phosphodiester approach was described. ▶ Phosphatidylcholine from egg yolk and DPPC were used as a source of phosphatide moiety. ▶ DCC and TsCl were the most efficient coupling agent.