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Guanylation Of Thiosemicarbazones: A New Synthetic Route To Polysubstituted Guanylhydrazones With Antimicrobial Activity

Silvio Cunha, G. Costa, Daniela Carvalho Neves, L. C. D. Souza, I. Vencato, J. R. Sabino, Carlito Lariucci
Published 2009 · Chemistry

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Guanil-hidrazonas poli-substituidas foram sintetizadas atraves da reacao de guanilacao de tiossemicarbazonas com aminas aromaticas e alifaticas, promovida HgCl 2 . Este metodo representa o primeiro emprego de tiossemicarbazonas como componente eletrofilico em reacoes de sintese de guanidinas mediadas por tiofilo, onde a introducao de cada substituinte dos nitrogenios das guanil-hidrazonas ocorreu de forma regiosseletiva. As atividades antibacteriana e antifungica foram avaliadas e alguns derivados mostraram atividade em valores pequenos de concentracao inibitoria minima e com amplo espectro de atividade. Estudou-se a estrutura cristalina de duas guanil-hidrazonas, determinando-se suas configuracoes e, as unicas interacoes relevantes observadas foram intermoleculares do tipo N–H...N e C–H...N. Thiosemicarbazones were employed for the first time as electrophiles in the guanylation reaction promoted by HgCl 2 , affording polysubstituted guanylhydrazones, with regioselective introduction of each nitrogen substituent. The antibacterial and antifungal activities of guanylhydrazones were evaluated by determination of minimal inhibitory concentrations. Some of them exhibited very low minimal inhibitory concentrations (MIC) and broad-spectrum activities. The configurations of two guanylhydrazones were assigned by X-ray analysis that also revealed intramolecular interactions of the type N–H...N and C–H...N.
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