Tonin Lilian T Düsman, Barbosa Valéria A, Bocca Cleverson Cassero, Ramos Erika R F, Nakamura Celso V, da Costa Willian Ferreira, Basso Ernani A, Nakamura Tânia U, Sarragiotto Maria Helena
Departamento de Química, Universidade Estadual de Maringá, Av. Colombo, 5790, CEP 87020-900, Maringá, PR, Brazil.
Eur J Med Chem. 2009 Apr;44(4):1745-50. doi: 10.1016/j.ejmech.2008.03.044. Epub 2008 Apr 10.
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.
合成了1-(间硝基)苯基和1-(对硝基)苯基-1,2,3,4-四氢-9H-β-咔啉-3-羧酸甲酯的顺式和反式异构体（化合物3a、b、4a和b），并对其体外抗克氏锥虫前鞭毛体形式进行了评估。在所有评估的四氢-β-咔啉衍生物中，发现反式-1-(间硝基)苯基-1,2,3,4-9H-四氢-β-咔啉-3-羧酸甲酯（3b）表现出显著的杀锥虫活性（IC(50)=22.2微摩尔）。对合成化合物和苯并硝唑进行了分子构象和电子性质的理论研究，以及循环伏安（CV）行为的测定。利用理论计算和循环伏安实验的结果，对硝基苯基-四氢-β-咔啉衍生物和苯并硝唑的杀锥虫活性进行了比较研究。
