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SYNTHESIS, CHARACTERIZATION AND IN VITRO ANTIFUNGAL EVALUATION OF NOVEL BENZIMIDAZO[1,2-c]QUINAZOLINES

2006; Sociedad Chilena de Química; Volume: 51; Issue: 2 Linguagem: Inglês

10.4067/s0717-97072006000200018

0717-9707

Braulio Insuasty, Harlen Torres, Jairo Quiroga, Rodrigo Abonı́a, Ricaurte Rodríguez, M. NOGERAS, Adalberto Sánchez, Claudio Saitz, Sandra Lorena Álvarez, Susana Zacchino,

Phenothiazines and Benzothiazines Synthesis and Activities

The synthesis of a series of new benzimidazo[1,2-c]quinazolines starting from 2-nitrobenzaldehyde and o-phenylendiamine is described. The structure elucidation of the products is based on detailed NMR analysis of experiments such as 1H-COSY, NOESY, DEPT, HSQC and HMBC. These compounds showed antifungal properties only against dermatophytes. Among them, those with electron-donor substituents on the 6-phenyl ring inhibited mainly T. rubrum and E. floccosum with MICs between 25-250 µg/mL and M. canis, M. gypseum and T. mentagrophytes with MICs between 50-250 µg/mL. Structures with electron-withdrawing substituents on the phenyl ring did not show any activities up to 250 µg/ml. Methyl substituents on the benzimidazole ring seem negatively affect the antifungal behaviour of this series