Design and synthesis of new adamantyl-substituted antileishmanial ether phospholipids

✍ Scribed by Ioannis Papanastasiou; Kyriakos C. Prousis; Kalliopi Georgikopoulou; Theofilos Pavlidis; Effie Scoulica; Nicolas Kolocouris; Theodora Calogeropoulou

• Publisher: Elsevier Science
• Year: 2010
• Tongue: English
• Weight: 360 KB
• Volume: 20
• Category: Article
• ISSN: 0960-894X
• DOI: 10.1016/j.bmcl.2010.07.078

✦ Synopsis

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}-N,N,N-trimethyl-ammonium inner salt (5b) and {2-[[[3-(2-octyloxy-ethyl)-adamant-1-yl]-ethoxy]hydroxyphosphinyloxy]ethyl}-N,N, N-trimethyl-ammonium inner salt (5c).