Design and synthesis of new adamantyl-substituted antileishmanial ether phospholipids.

Abstract

A series of new 2-[3-(2-alkyloxy-ethyl)-adamantan-1-yl]-ethoxy substituted ether phospholipids was synthesized and their antileishmanial activity was evaluated against Leishmania infantum amastigotes. The majority of the new analogues were significantly less cytotoxic than miltefosine while, antiparasitic activity depended on the length of the 2-alkyloxy substituent. The most potent compounds were {2-[[[3-(2-hexyloxy-ethyl)-adamant-1-yl]-ethoxy]hydroxyphosphinyloxy]ethyl}-Nu,Nu,Nu-trimethyl-ammonium inner salt (5b) and {2-[[[3-(2-octyloxy-ethyl)-adamant-1-yl]-ethoxy]hydroxyphosphinyloxy]ethyl}-Nu,Nu,Nu-trimethyl-ammonium inner salt (5c).

DOI: 10.1016/j.bmcl.2010.07.078

Cite this paper

@article{Papanastasiou2010DesignAS, title={Design and synthesis of new adamantyl-substituted antileishmanial ether phospholipids.}, author={Ioannis Papanastasiou and Kyriakos C. Prousis and Kalliopi Georgikopoulou and Theofilos Pavlidis and Efstathia V Scoulica and Nicolas Kolocouris and Theodora Calogeropoulou}, journal={Bioorganic & medicinal chemistry letters}, year={2010}, volume={20 18}, pages={5484-7} }