Original quinazoline derivatives displaying antiplasmodial properties

European Journal of Medicinal Chemistry
Youssef KabriPatrice Vanelle

Abstract

The multistep synthesis of new quinazoline-derived molecules and their in vitro antiplasmodial evaluation on the W2 chloroquino-resistant Plasmodium falciparum strain is described herein. These molecules have also been studied concerning their in vitro cytotoxicity toward two human cell lines (K652 and HepG2) in order to calculate their respective selectivity indexes (S.I.). Among the fourteen tested molecules, two exhibited both significant antiplasmodial activity (IC(50)=0.95 and 1.3 microM) and low toxicity (IC(50)>100 or 125 microM), compared with two reference drugs: chloroquine and doxycycline. The structure activity relationships establish that the molecular scaffold which exerts the best profile is the 6-nitro-2-(tosylmethyl)-N-(3-substituted-phenyl)-quinazolin-4-amine. The hit molecules were finally investigated regarding their potential action toward two other protozoa, Leishmania donovani and Toxoplasma gondii, showing that these molecules display a selective antiplasmodial activity.

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Citations

Oct 8, 2013·European Journal of Medicinal Chemistry·Marc SinceMichel Boulouard
Mar 13, 2014·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Abdelmadjid BenmohammedPatrice Vanelle
Jun 20, 2014·European Journal of Medicinal Chemistry·Nicolas PrimasNadine Azas
Nov 13, 2013·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Leping YeXiaodong Xia
Dec 1, 2015·European Journal of Medicinal Chemistry·Syed Muhammad SaadM Iqbal Choudhary
Aug 15, 2012·European Journal of Medicinal Chemistry·Anita CohenNadine Azas
Mar 9, 2012·Biomedicine & Pharmacotherapy = Biomédecine & Pharmacothérapie·Armand GellisNadine Azas
Mar 5, 2016·Chemical Reviews·Manoj B GawandeRajender S Varma
Oct 6, 2014·European Journal of Medicinal Chemistry·Clémence TabéléPatrice Vanelle
May 23, 2012·European Journal of Medicinal Chemistry·Lucie PaloquePatrice Vanelle
Dec 14, 2011·Biochimica Et Biophysica Acta·Yareli Rojas-AguirreMario Suwalsky
May 26, 2015·European Journal of Medicinal Chemistry·Rammohan R YadavSandip B Bharate
Jan 7, 2015·European Journal of Medicinal Chemistry·Charline KiefferPatrice Vanelle
Jul 7, 2012·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Nicolas PrimasPatrice Vanelle
Apr 30, 2010·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Martine Maillard-BoyerPatrice Vanelle
Jul 27, 2010·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Youssef KabriPatrice Vanelle
Oct 22, 2015·BMC Research Notes·Yihenew Simegniew BirhanAriaya Hymete
Mar 3, 2021·Molecular Diversity·Oluwatoyin BabatundeShahnaz Perveen
Jan 23, 2014·Journal of Medicinal Chemistry·Diego González CabreraKelly Chibale

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