Find in Library

As part of our ongoing antikinetoplastid structure–activity relationship study focused on positions 2 and 8 of the 3-nitroimidazo[1,2-<i>a</i>]pyridine scaffold, we were able to introduce a phenylthioether moiety at both position 2 and position 8 in one step. Using a previously reported synthetic route developed in our laboratory, we obtained 6-chloro-3-nitro-8-(phenylthio)-2-[(phenylthio)methyl]imidazo[1,2-<i>a</i>]pyridine in 74% yield. The in vitro cell viability of this compound was assessed on the HepG2 cell line, and its in vitro activity was evaluated against the promastigote form of <i>L. donovani</i>, the axenic amastigote form of <i>L. infantum</i> and the trypomastigote blood stream form of <i>T. b. brucei</i>. It showed low solubility in HepG2 culture medium (CC₅₀ > 7.8 µM), associated with weak activity against both the promastigote form of <i>L. donovani</i> (EC₅₀ = 8.8 µM), the axenic amastigote form of <i>L. infantum</i> (EC₅₀ = 9.7 µM) and the trypomastigote blood stream form of <i>T. b. brucei</i> (EC₅₀ = 12.8 µM).