Synthesis, characterization and in vitro antifungal evaluation of novel benzimidazo[1,2-c]quinazolines

• B. A. INSUASTY ^[1] ; H. TORRES ^[2] ; J. QUIROGA ^[1] ; R. ABONÍA ^[1] ; R. RODRÍGUEZ ^[2] ; M. NOGERAS ^[3] ; A. SÁNCHEZ ^[3] ; C. SAITZ ^[4] ; S. L. ALVAREZ ^[5] ; S. A. ZACCHINO ^[5]
  1. [1] Universidad del Valle (Colombia)

     Universidad del Valle (Colombia)

     Colombia

     
  2. [2] Universidad Nacional de Colombia

     Universidad Nacional de Colombia

     Colombia

     
  3. [3] Universidad de Jaén

     Universidad de Jaén

     Jaén, España

     
  4. [4] Universidad de Chile

     Universidad de Chile

     Santiago, Chile

     
  5. [5] Universidad Nacional de Rosario

     Universidad Nacional de Rosario

     Argentina

     

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• Localización: Journal of the Chilean Chemical Society (Boletín de la Sociedad Chilena de Química), ISSN-e 0717-6309, ISSN 0366-1644, Vol. 51, Nº. 2, 2006, págs. 927-932
• Idioma: inglés
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• Resumen

  • 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