2. Academic Validation
  3. Design and synthesis of new adamantyl-substituted antileishmanial ether phospholipids

Design and synthesis of new adamantyl-substituted antileishmanial ether phospholipids

  • Bioorg Med Chem Lett. 2010 Sep 15;20(18):5484-7. doi: 10.1016/j.bmcl.2010.07.078.
Ioannis Papanastasiou 1,  Kyriakos C Prousis,  Kalliopi Georgikopoulou,  Theofilos Pavlidis,  Effie Scoulica,  Nicolas Kolocouris,  Theodora Calogeropoulou
Affiliations

Affiliation

  • 1 Faculty of Pharmacy, Department of Pharmaceutical Chemistry, University of Athens, Panepistimioupoli-Zografou, Athens 15771, Greece.
PMID: 20719503 DOI: 10.1016/j.bmcl.2010.07.078
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).

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