A New Synthetic Route to Original Sulfonamide Derivatives in 2-Trichloromethylquinazoline Series: A Structure-Activity Relationship Study of Antiplasmodial Activity

Molecules

Nicolas Primas¹  Pierre Verhaeghe¹  Anita Cohen¹  Charline Kieffer¹  Aurélien Dumètre¹  Sébastien Hutter¹  Sylvain Rault¹  Pascal Rathelot¹  Nadine Azas¹ 

[1] ¹Laboratoire de Pharmacochimie Radicalaire, Faculté de Pharmacie, Institut de Chimie Radicalaire UMR CNRS 7273, Aix-Marseille Univ, 27 Boulevard Jean Moulin, 13385 Marseille cedex 05, France

关键词: quinazoline;    trichloromethyl group;    sulfonamide;    microwaves;    antiplasmodial activity;   

DOI  :  10.3390/molecules17078105

来源: mdpi

【 摘 要 】

We report herein a simple and efficient two-step synthetic approach to new 2-trichloromethylquinazolines possessing a variously substituted sulfonamide group at position 4 used to prepare new quinazolines with antiparasitic properties. Thus, an original series of 20 derivatives was synthesized, which proved to be less-toxic than previously synthesized hits on the human HepG2 cell line, but did not display significant antiplasmodial activity. A brief Structure-Activity Relationship (SAR) evaluation shows that a more restricted conformational freedom is probably necessary for providing antiplasmodial activity.

【 授权许可】

CC BY   
This is an open access article distributed under the Creative Commons Attribution License (CC BY) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.