Comparative study of the trypanocidal activity of the methyl 1-nitrophenyl-1,2,3,4-9H-tetrahydro-beta-carboline-3-carboxylate derivatives and benznidazole using theoretical calculations and cyclic voltammetry.
The cis and trans isomers of methyl 1-(m-nitro)phenyl and 1-(p-nitro)phenyl-1,2,3,4-tetrahydro-9H-beta-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-beta-carboline derivatives, the compound trans-methyl 1-(m-nitro)phenyl-1,2,3,4-9H-tetrahydro-beta-carboline-3-carboxylate (3b) was found to exhibit significant trypanocidal activity (IC(50)=22.2 microM). 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-beta-carbolines derivatives and benznidazole, using the results of theoretical calculations and of the cyclic voltammetry experiments, is presented.
Tonin
Lilian T Düsman
LT
Departamento de Química, Universidade Estadual de Maringá, Av. Colombo, 5790, CEP 87020-900, Maringá, PR, Brazil.
Barbosa
Valéria A
VA
Bocca
Cleverson Cassero
CC
Ramos
Erika R F
ER
Nakamura
Celso V
CV
da Costa
Willian Ferreira
WF
Basso
Ernani A
EA
Nakamura
Tânia U
TU
Sarragiotto
Maria Helena
MH
D000818:Animals; D002264:Carboxylic Acids / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D004563:Electrochemistry; D008958:Models, Molecular; D008968:Molecular Conformation; D009593:Nitroimidazoles / Q000494:pharmacology*; D055672:Static Electricity; D013237:Stereoisomerism; D014344:Trypanocidal Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D014349:Trypanosoma cruzi / Q000187:drug effects*
D002264:Carboxylic Acids; D009593:Nitroimidazoles; D014344:Trypanocidal Agents; C009999:benzonidazole