Theoretical studies of the tautomerism in 3-(2-R-Phenylhydrazono)-naphthalene- 1,2,4-triones: synthesis of copper(II) complexes and studies of antibacterial and antitumor activities

Journal of the Brazilian Chemical Society

Marinho Filho, José D. B.¹  Moraes, Manoel O. de¹  Mangrich, Antonio S.¹  Universidade Federal Fluminense¹  FIOCRUZ, Rio de Janeiro, Brazil¹  Carneiro, J. Walkimar de M.¹  Francisco, Acácio I.¹  Casellato, Annelise¹  Fragoso, Thaís P.¹  Silva, Fernando de C. da¹  Universidade Federal do Rio de Janeiro, Rio de Janeiro, Brazil¹  Universidade Federal do Ceará, Fortaleza, Brazil¹  Vargas, Maria D.¹  Costa-Lotufo, Letícia V.¹  Barbosa, Jussara P.¹  Ferreira, Vitor F.¹  Universidade Federal do Paraná, Curitiba, Brazil¹  Pessoa, Claudia¹ 

关键词: naphthoquinones;    copper(II) complexes;    tautomerism;    hydrazone compounds;    antibacterial activity;    antitumor activity;   

DOI  :  10.1590/S0103-50532010000700017

学科分类：化学（综合）

来源: SciELO

【 摘 要 】

DFT calculations using the B3LYP and PBE1PBE functionals with the standard 6-31G(d) and 6-311+G(2d,p) basis sets were carried out for the 3-(2-phenylhydrazone)-naphthalene-1,2,4-trione system in solution (dmso) and in the gas phase, and showed the keto-hydrazone forms (rotamers Ia and Ib) to be more stable than the enol-azo forms (rotamers IIa and IIb, by about 14 kcal mol-1) and III (by approximately 6 kcal mol-1), independently of the nature of the substituent in the phenylene ring. These results were confirmed by spectroscopic data on the derivatives HL1-HL13, obtained from 2-hydroxy-1,4-naphthoquinone and arylamines (R = 4-OMe, 4-N2-C6H5, 4-Cl, 4-I, 3-I, 2-I, 4-COOH, 3-COOH, 4-CN, 3-CN, 4-NO2, 3-NO2, 2-NO2). The in vitro antitumor (against SF-295, HCT-8, MDAMB-435 and HL-60 cancer cell lines) and antibacterial activities (Bacillus cereus, Bacillus subtilis, Enterococcus faecalis, Staphylococcus aureus, Escherichia coli, Klebsiella pneumonia and Pseudomonas aeruginosa) of compounds HL1-HL13 and of their respective copper(II) complexes, [Cu(L1-13)2], were tested. In general, these compounds exhibited low antibacterial activity, except for HL5 (R = 3-I), more active than the control; however, the corresponding complex was inactive. In contrast, increased cytotoxicity was observed upon complexation. Complex [Cu(L13)2] (R = 3-NO2) presented moderate cytotoxicity against human leukemia (HL-60).

【 授权许可】

Unknown