Synthesis of Novel G Factor or Chloroquine-Artemisinin Hybrids and Conjugates with Potent Antiplasmodial Activity

ACS Medicinal Chemistry Letters
2020.0

Abstract

A series of novel hybrids of artemisinin (ART) with either a phytormone endoperoxide G factor analogue (GMeP) or chloroquine (CQ) and conjugates of the same compounds with the polyamines (PAs), spermidine (Spd), and homospermidine (Hsd) were synthesized and their antiplasmodial activity was evaluated using the CQ-resistant <i>P. falciparum</i> FcB1/Colombia strain. The ART-GMeP hybrid <b>5</b> and compounds <b>9</b> and <b>10</b> which are conjugates of Spd and Hsd with two molecules of ART and one molecule of GMeP, were the most potent with IC<sub>50</sub> values of 2.6, 8.4, and 10.6 nM, respectively. The same compounds also presented the highest selectivity indexes against the primary human fibroblast cell line AB943 ranging from 16 372 for the hybrid <b>5</b> to 983 for the conjugate <b>10</b> of Hsd.

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