Synthesis of a small library of 2-phenoxy-1,4-naphthoquinone and 2-phenoxy-1,4-anthraquinone derivatives bearing anti-trypanosomal and anti-leishmanial activity.
Taking advantage of the structural features of natural products showing anti-trypanosomatid activity, we designed and synthesized a small library of 2-phenoxy-1,4-naphthoquinone and 2-phenoxy-1,4-anthraquinone derivatives. The library was obtained following a parallel approach and using readily available synthons. All the derivatives showed inhibitory activity toward either Trypanosoma or Leishmania species, with 8, 10, and 16 being the most active compounds against Trypanosoma brucei rhodesiense, Leishmania donovani, and Trypanosoma cruzi cells (IC(50)=50nM, IC(50)=0.28microM, and IC(50)=1.26microM, respectively).
Bolognesi
Maria Laura
ML
Department of Pharmaceutical Sciences, Alma Mater Studiorum, Bologna University, Via Belmeloro 6, I-40126 Bologna, Italy. marialaura.bolognesi@unibo.it
Lizzi
Federica
F
Perozzo
Remo
R
Brun
Reto
R
Cavalli
Andrea
A
D000818:Animals; D000880:Anthraquinones / Q000138:chemical synthesis / Q000494:pharmacology*; D000981:Antiprotozoal Agents / Q000138:chemical synthesis / Q000494:pharmacology*; D015195:Drug Design; D020128:Inhibitory Concentration 50; D007891:Leishmania / Q000187:drug effects*; D008956:Models, Chemical; D009285:Naphthoquinones / Q000138:chemical synthesis / Q000494:pharmacology*; D021261:Parasitic Sensitivity Tests; D014345:Trypanosoma / Q000187:drug effects*
D000880:Anthraquinones; D000981:Antiprotozoal Agents; D009285:Naphthoquinones