期刊论文详细信息
Journal of the Brazilian Chemical Society
Novel aminonaphthoquinone mannich bases derived from lawsone and their copper(II) complexes: synthesis, characterization and antibacterial activity
Costa, Gisela L. da1  Barbosa, Cláudia C.1  Instituto Oswaldo Cruz, Rio de Janeiro, Brazil1  Greco, Sandro J.1  Universidade Federal de Minas Gerais, Belo Horizonte, Brazil1  Universidade Federal do Rio de Janeiro, Rio de Janeiro, Brazil1  Vargas, Maria D.1  Mangrich, Antônio S.1  Universidade Federal Fluminense, Niterói, Brazil1  Visentin, Lorenzo C.1  Barbosa, Jussara P.1  Universidade Federal do Paraná, Curitiba, Brazil1  Pinheiro, Carlos B.1  Neves, Amanda P.1 
关键词: aminonaphthoquinones;    copper complexes;    Mannich bases;    crystal structure determination;    antibacterial activity;   
DOI  :  10.1590/S0103-50532009000400015
学科分类:化学(综合)
来源: SciELO
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【 摘 要 】

A series of novel Mannich bases (HL1-HL13) derived from 2-hydroxy-1,4-naphthoquinone (lawsone), substituted benzaldehydes [C6H2R1R2R3C(O)H] and various primary amines (NH2R4, R4 = n-butyl, benzyl, allyl, 2-furfuryl), and their Cu2+ complexes, [Cu(L1)2]-[Cu(L13)2], have been synthesized and fully characterized by analytical and spectroscopic methods. The structures of complexes 1(R1 = R2 = R3 = H; R4 = Bu), 2(R1 = R3 = H; R2 = NO2; R4= Bu) and 7 (R1 = OH; R2 = R3 = H; R4= Bu) were determined by single crystal X-ray diffraction studies. All complexes crystallize in centrosymmetric space groups, with a copper atom in the inversion centre. Two L- coordinate through the naphthalen-2-olate oxygen and secondary amine-N atoms, forming six-membered chelate rings around the copper atom in a trans-N2O2 environment; spectroscopic data confirm that the other complexes exhibit similar molecular arrangement. The antimicrobial activity of all compounds has been tested on seven different strains of bacteria: Bacillus cereus, Bacillus subtilis, Escherichia coli, Enterococcus faecalis, Klebsiella pneumoniae, Pseudomonas aeruginosaand Staphylococcus aureus. In general, Mannich bases were more active than complexes, HL11(R1 = OH; R2 =H; R3 = Me; R4= Bn) and HL13(R1 = OH; R2 = H; R3 = Br; R4= Bn) being the most potent inhibitors. The MIC for the most active compound HL11against S. Coliwas 20 µmol L-1 (8 µg mL-1), better than Chloramphenicol (90 µmol L-1) and well below most values reported for other naphthoquinones.

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