European Journal of Medicinal Chemistry p. 1745 - 1750 (2009)
Update date:2022-09-26
Topics:
Duesman Tonin, Lilian T.
Barbosa, Valeria A.
Bocca, Cleverson Cassero
Ramos, Erika R.F.
Nakamura, Celso V.
Ferreira da Costa, Willian
Basso, Ernani A.
Nakamura, Tania U.
Sarragiotto, Maria Helena
The cis and trans isomers of methyl 1-(m-nitro)phenyl and 1-(p-nitro)phenyl-1,2,3,4-tetrahydro-9H-β-carboline-3-carboxylates (compounds 3a,b, 4a and b) were synthesized and evaluated in vitro against epimastigote forms of Trypanosoma cruzi. Among all of the evaluated tetrahydro-β-carboline derivatives, the compound trans-methyl 1-(m-nitro)phenyl-1,2,3,4-9H-tetrahydro-β-carboline-3-carboxylate (3b) was found to exhibit significant trypanocidal activity (IC50 = 22.2 μM). Theoretical studies of molecular conformations and electronic properties for the synthesized compounds and benznidazole, as well as, the cyclic voltammetric (CV) behaviors' determination were performed. A comparative study of the trypanocidal activity of the nitrophenyl-tetrahydro-β-carbolines derivatives and benznidazole, using the results of theoretical calculations and of the cyclic voltammetry experiments, is presented.
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