Molecules 2012, 17(7), 8105-8117; doi:10.3390/molecules17078105
Article

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

1 Laboratoire 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 2 Infections Parasitaires, Transmission, Physiopathologie et Thérapeutique, UMR MD3, Faculté de Pharmacie, Aix-Marseille Univ, 27 Boulevard Jean Moulin, 13385 Marseille Cedex 05, France 3 Centre d’Etudes et de Recherche sur le Médicament de Normandie, UPRES EA 4258, FR CNRS 3038 INC3M, UFR des Sciences Pharmaceutiques, Université de Caen Basse Normandie, Boulevard Becquerel, 14032 Caen Cedex, France
* Author to whom correspondence should be addressed.
Received: 14 May 2012; in revised form: 25 June 2012 / Accepted: 26 June 2012 / Published: 5 July 2012
(This article belongs to the Section Organic Synthesis)
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Abstract: 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.
Keywords: quinazoline; trichloromethyl group; sulfonamide; microwaves; antiplasmodial activity

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MDPI and ACS Style

Primas, N.; Verhaeghe, P.; Cohen, A.; Kieffer, C.; Dumètre, A.; Hutter, S.; Rault, S.; Rathelot, P.; Azas, N.; Vanelle, P. A New Synthetic Route to Original Sulfonamide Derivatives in 2-Trichloromethylquinazoline Series: A Structure-Activity Relationship Study of Antiplasmodial Activity. Molecules 2012, 17, 8105-8117.

AMA Style

Primas N, Verhaeghe P, Cohen A, Kieffer C, Dumètre A, Hutter S, Rault S, Rathelot P, Azas N, Vanelle P. A New Synthetic Route to Original Sulfonamide Derivatives in 2-Trichloromethylquinazoline Series: A Structure-Activity Relationship Study of Antiplasmodial Activity. Molecules. 2012; 17(7):8105-8117.

Chicago/Turabian Style

Primas, Nicolas; Verhaeghe, Pierre; Cohen, Anita; Kieffer, Charline; Dumètre, Aurélien; Hutter, Sébastien; Rault, Sylvain; Rathelot, Pascal; Azas, Nadine; Vanelle, Patrice. 2012. "A New Synthetic Route to Original Sulfonamide Derivatives in 2-Trichloromethylquinazoline Series: A Structure-Activity Relationship Study of Antiplasmodial Activity." Molecules 17, no. 7: 8105-8117.

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