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2-Acetylpyridine- and 2-benzoylpyridine-derived thiosemicarbazones and their antimony(III) complexes exhibit high anti-trypanosomal activity |
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| Authors: | Gabrieli L. ParrilhaRoberta P. Dias,Willian R. RochaIsolda C. Mendes,Diego Bení tezJavier Varela,Hugo CerecettoMercedes Gonzá lez,Cristiane M.L. MeloJuliana K.A.L. Neves,Valé ria R.A. PereiraHeloisa Beraldo |
| Affiliation: | a Departamento de Química, Universidade Federal de Minas Gerais, 31270-901 Belo Horizonte, MG, Brazil b Escola de Belas Artes, Universidade Federal de Minas Gerais, 31270-901 Belo Horizonte, MG, Brazil c Grupo de Química Medicinal, Laboratório de Química Orgânica Facultad de Ciencias/Facultad de Química, Universidad de la República, 11400 Montevideo, Uruguay d Laboratório de Imunogenética, Departamento de Imunologia, Instituto Aggeu Magalhães, Fiocruz, PE, Brazil |
| Abstract: | Complexes [Sb(2Ac4oClPh)Cl2] (1), [Sb(2Ac4oFPh)Cl2] (2), [Sb(2Ac4oNO2Ph)Cl2] (3), [Sb(2Bz4oClPh)Cl2] (4), [Sb(2Bz4oFPh)Cl2] (5) and [Sb(2Bz4oNO2Ph)Cl2] (6) were obtained with 2-acetylpyridine-N(4)-ortho-chlorophenyl thiosemicarbazone (H2Ac4oClPh) and its N(4)-ortho-fluor (H2Ac4oFPh) and N(4)-ortho-nitro (H2Ac4oNO2Ph) analogues, and with the corresponding 2-benzoylpyridine-derived thiosemicarbazones (H2Bz4oClPh, H2Bz4oFPh, H2Bz4oNO2Ph). The studied compounds are excellent inhibitors of Trypanosoma cruzi growth. H2Bz4oClPh and complexes (4) and (1) were the most trypanosomicidal.Upon coordination of H2Ac4oClPh to antimony(III) in 1, the therapeutic index (TI) goes from 10.58 to 14.35. However, the best values of TI were found for H2Bz4oClPh (TI = 1240) and H2Ac4oNO2Ph (TI = 773). Structure-activity relationship (SAR) studies did not allow the establishment of correlations between the anti-trypanosomal activity and physico-chemical parameters, but correlations were found between the cytotoxicities and physico-chemical properties. |
| Keywords: | Thiosemicarbazones Antimony(III) complexes Anti-trypanosomal activity SAR studies |
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