Síntese e caracterização estrutural de N,N`-Diaribenzomidinas com atividade Leishmanicida

AUTOR(ES)

Cláudio Eduardo Rodrigues dos Santos

DATA DE PUBLICAÇÃO

2004

RESUMO

The synthesis of fourteen amidine derivatives of N,N-diarylbenzamidine class in the neutral and saline forms were realized by two methodologies. Basically, in both synthetical methods the same starting reagents were utilized, but involving a solid reaction and reflux conditions, respectively. The structural characterization was realized by spectroscopic techniques such as IR, MS, NMR 1H and 13C. The NOEDIF experiment, further the traditional spectrometric methods and molecular modeling calculations, allowed elucidate the E stereoisomer in aminic tautomeric form related to methoxy moiety in N-(pmethoxyphenyl)- N-phenylbenzamidine and, E and Z mixture with iminic tautomeric form related to nitro group in N-(p-nitrophenyl)-N-phenylbenzamidine derivative. The benzamidine pKa(s) values were determined by potentiometric method, and a linear correlation with amidinic carbon chemical shifts was verified indicating an electronic effect transmission over the basicity. The new amidine derivatives were assayed against Leishmania genera parasites, such as L. amazonensis, braziliensis and chagasi, showing a promising activity in the saline forms. The di-methoxy and nitro-derivatives presented the best anti-leishmanial activities.

ASSUNTO(S)

síntese leishmania quimica organica

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