title: 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).
authors: Faculty of Pharmacy, Department of Pharmaceutical Chemistry, University of Athens, Panepistimioupoli-Zografou, Athens 15771, Greece.
authors: Ioannis
authors: I
authors: Papanastasiou
authors: Kyriakos C
authors: KC
authors: Prousis
authors: Kalliopi
authors: K
authors: Georgikopoulou
authors: Theofilos
authors: T
authors: Pavlidis
authors: Effie
authors: E
authors: Scoulica
authors: Nicolas
authors: N
authors: Kolocouris
authors: Theodora
authors: T
authors: Calogeropoulou
mesh_terms: D000981:Antiprotozoal Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D002460:Cell Line; D002470:Cell Survival; D006801:Humans; D018314:Leishmania infantum / Q000187:drug effects*; D007898:Leishmaniasis, Visceral / Q000188:drug therapy*; D008264:Macrophages / Q000187:drug effects; D010742:Phospholipid Ethers / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D010767:Phosphorylcholine / Q000031:analogs & derivatives / Q000494:pharmacology
chemical_list: D000981:Antiprotozoal Agents; D010742:Phospholipid Ethers; D010767:Phosphorylcholine; C039128:miltefosine