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Cerecetto, H. et al.

Cerecetto, Di Maio, González, Risso, Sagrera, Seoane, Denicola, Peluffo, Quijano, Stoppani, Paulino, Olea-Azar, Basombrío,

Synthesis and antitrypanosomal evaluation of E-isomers of 5-nitro-2-furaldehyde and 5-nitrothiophene-2-carboxaldehyde semicarbazone derivatives. structure-activity relationships.

Several novel semicarbazone derivatives were prepared from 5-nitro-2-furaldehyde or 5-nitrothiophene-2-carboxaldehyde and semicarbazides bearing a spermidine-mimetic moiety. All derivatives presented the E-configuration, as determined by NMR-NOE experiments. These compounds were tested in vitro as potential antitrypanosomal agents, and some of them, together with the parent compounds, 5-nitro-2-furaldehyde and 5-nitrothiophene-2-carboxaldehyde semicarbazone derivatives, were also evaluated in vivo using infected mice. Structure-activity relationship studies were carried out using voltammetric response and lipophilic-hydrophilic balance as parameters. Two of the compounds (1 and 3) displayed the highest in vivo activity. A correlation was found between lipophilic-hydrophilic properties and trypanocidal activity, high R(M) values being associated with low in vivo effects.[1]

References

Synthesis and antitrypanosomal evaluation of E-isomers of 5-nitro-2-furaldehyde and 5-nitrothiophene-2-carboxaldehyde semicarbazone derivatives. structure-activity relationships. Cerecetto, H., Di Maio, R., González, M., Risso, M., Sagrera, G., Seoane, G., Denicola, A., Peluffo, G., Quijano, C., Stoppani, A.O., Paulino, M., Olea-Azar, C., Basombrío, M.A. European journal of medicinal chemistry. (2000) [Pubmed]

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