Tandem synthesis and in vitro antiplasmodial evaluation of new naphtho[2,1-d] thiazole derivatives

Anita Cohen; Pierre Verhaeghe; Maxime D. Crozet; Sébastien Hutter; Pascal Rathelot; Patrice Vanelle; Nadine Azas

doi:10.1016/j.ejmech.2012.07.034

Journal articles

Tandem synthesis and in vitro antiplasmodial evaluation of new naphtho[2,1-d] thiazole derivatives

Anita Cohen ¹ Pierre Verhaeghe ² Maxime D. Crozet ³ Sébastien Hutter ¹ Pascal Rathelot ⁴ Patrice Vanelle ⁴ Nadine Azas ¹

1 IP-TPT - Infections Parasitaires : Transmission, Physiopathologie et Thérapeutiques

2 LCC - Laboratoire de chimie de coordination

3 CBRL - Chimie, biologie et radicaux libres - UMR 6517

4 ICR - Institut de Chimie Radicalaire

Abstract : A series of naphtho[2,1-d]thiazoles was prepared in good yields under microwave irradiation with an original protocol combining tandem direct arylation and intramolecular Knoevenagel reaction on 1,3-thiazole derivatives. Antiplasmodial evaluation of this series highlighted two hit compounds (compounds 11 and 13) displaying promising in vitro activity on the multiresistant K1 Plasmodium falciparum strain. Structure-toxicity and structure activity relationships are also discussed and reveal the importance of the R-1 and R-4 substituents of the naphthyl moiety for the biological profile of the series. (C) 2012 Elsevier Masson SAS. All rights reserved.

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Journal articles

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Chemical Sciences

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Tandem synthesis and in vitro antiplasmodial evaluation of new naphtho[2,1-d] thiazole derivatives

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Tandem synthesis and in vitro antiplasmodial evaluation of new naphtho[2,1-d] thiazole derivatives

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