@article{3061850, title = "Design and synthesis of new adamantyl-substituted antileishmanial ether phospholipids", author = "Papanastasiou, I. and Prousis, K.C. and Georgikopoulou, K. and Pavlidis, T. and Scoulica, E. and Kolocouris, N. and Calogeropoulou, T.", journal = "Bioorganic and Medicinal Chemistry Letters", year = "2010", volume = "20", number = "18", pages = "5484-5487", doi = "10.1016/j.bmcl.2010.07.078", keywords = "[2 [[[3 (2 hexyloxy ethyl) adamant 1 yl] ethoxy] hydroxyphosphinyloxy] ethyl] n,n,n trimethyl ammonium inner salt; [2 [[[3 (2 octyloxy ethyl) adamant 1 yl] ethoxy] hydroxyphosphinyloxy] ethyl] n,n,n trimethyl ammonium inner salt; antileishmanial agent; miltefosine; phospholipid derivative; unclassified drug, amastigote; amino acid substitution; antileishmanial activity; article; controlled study; drug activity; drug cytotoxicity; drug design; drug synthesis; Leishmania infantum; macrophage activation; nonhuman, Antiprotozoal Agents; Cell Line; Cell Survival; Humans; Leishmania infantum; Leishmaniasis, Visceral; Macrophages; Phospholipid Ethers; Phosphorylcholine, Leishmania infantum", 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-Ν,Ν,Ν-trimethyl-ammonium inner salt (5b) and 2-[[[3-(2-octyloxy-ethyl)-adamant-1-yl]-ethoxy]hydroxyphosphinyloxy]ethyl- Ν,Ν,Ν-trimethyl-ammonium inner salt (5c). © 2010 Elsevier Ltd. All rights reserved." }