Hydroxynaphthoquinone Metal Complexes as Antitumor Agents X: Synthesis, Structure, Spectroscopy and <i>In Vitro</i> Antitumor Activity of 3‐Methyl‐Phenylazo Lawsone Derivatives and Their Metal Complexes Against Human Breast Cancer Cell Line MCF‐7

Gokhale, Nikhil H.; Padhyé, Subhash; Newton, C. J.; Pritchard, Robin G.

doi:10.1155/mbd.2000.121

Cited by 31 publications

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“…26,30 See Supplementary Information for description on the synthesis, analytical and spectroscopic data of the novel products.…”

Section: Synthesis Of the Hydrazono Compounds Hl1-hl13mentioning

confidence: 99%

“…26,27 Complexes 1-13 ( Figure 3) were obtained by addition of triethylamine to a methanol suspension of HLn (n = 1-13) and CuCl 2…”

Section: Synthesis and Characterization Of The Copper(ii) Complexesmentioning

confidence: 99%

“…25 Incorporation of an azo group into 2-hydroxy-1,4-naphthoquinone has led to promising antimalarial and anticancer agents, in which metal complexation with copper(II) resulted in increased cytotoxicity. 26,27 The derivatives can be represented by several tautomeric structures illustrated in Figure 1: 3-(2-R-phenylhydrazono)-naphthalene-1,2,4-triones, Ia and Ib, 3-R-arylazo-4-hydroxy-1,2-naphthoquinones, IIa and IIb, and 3-R-arylazo-2-hydroxy-1,4-naphthoquinone III. A poor X-ray diffraction study of the derivative containing R=3-Me suggested that this compound exists as tautomer IIa in the solid state.…”

Section: Introductionmentioning

confidence: 99%

“…26,27 In the present work we describe the results of our theoretical calculations using density functional theory (DFT) carried out to investigate the relative stability of the tautomeric forms of 3-(2-R-phenylhydrazono)-naphthalene-1,2,4-trione derivatives (Figure 1) as a function of the substituent, both in the gas phase and in solution. Low solubility prevented experimental NMR experiments.25 Some of these compounds have been previously described, 26,27,30,31 …”

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confidence: 99%

“…26,27 The derivatives can be represented by several tautomeric structures illustrated in Figure 1: 3-(2-R-phenylhydrazono)-naphthalene-1,2,4-triones, Ia and Ib, 3-R-arylazo-4-hydroxy-1,2-naphthoquinones, IIa and IIb, and 3-R-arylazo-2-hydroxy-1,4-naphthoquinone III. A poor X-ray diffraction study of the derivative containing R=3-Me suggested that this compound exists as tautomer IIa in the solid state.…”

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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

Francisco

Vargas

Fragoso

et al. 2010

J. Braz. Chem. Soc.

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Cálculos teóricos utilizando os funcionais B3LYP e PBE1PBE e as bases 6-31G(d) e 6-311+G(2d,p) para o sistema 3-(2-fenil-hidrazona)-naftaleno-1,2,4-triona, em solução (dmso) e em fase gasosa, evidenciaram, em ambos os casos, a maior estabilidade da forma ceto-hidrazona (rotâmeros Ia e Ib) comparada às formas enol-azo (rotâmeros IIa/IIb, por volta de 14 kcal mol -1 ) e III (aproximadamente 6 kcal mol -1 ). A natureza do substituinte no grupo fenil não influenciou a estabilidade relativa dos tautômeros. Estes resultados foram confirmados por dados espectroscópicos dos derivados HL1-HL13, sintetizados a partir da 2-hidroxi-1,4-naftoquinona e arilaminas (R = 4-OMe, 4-N 2 -C 6 H 5 , 4-Cl, 4-I, 3-I, 2-I, 4-COOH, 3-COOH, 4-CN, 3-CN, 4-NO 2 , 3-NO 2 , 2-NO 2 ). A avaliação da atividade anticâncer in vitro (contra linhagens de células cancerosas SF-295, HCT-8, MDAMB-435 e HL-60) e bactericida (Bacillus cereus, Bacillus subtilis, Enterococcus faecalis, Staphylococcus aureus, Escherichia coli, Klebsiella pneumonia e Pseudomonas aeruginosa) dos compostos HL1-HL13 e dos seus respectivos complexos de cobre(II), 2 ], foi avaliada. Em geral a atividade bactericida foi baixa, exceto para o derivado HL5 (R = 3-I), mais ativo do que o controle; entretanto, seu complexo não foi ativo. Por outro lado, a complexação levou, em geral, ao aumento da atividade antitumoral dos pré-ligantes. O complexo [Cu(L13) 2 ] (R = 3-NO 2 ) apresentou moderada citotoxicidade contra leucemia humana (HL-60).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 ), 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-N 2 -C 6 H 5 , 4-Cl, 4-I, 3-I, 2-I, 4-COOH, 3-COOH, 4-CN, 3-CN, 4-NO 2 , 3-NO 2 , 2-NO 2 ). 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, ) 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-NO 2 ) presented moderate cytotoxicity against human leukemia (HL-60).Keywords: naphthoquinones, copper(II) complexes, tautomerism, hydrazone compounds, antibacterial activity, antitumor activity Theoretical Studies of the Tautomerism in 3-(2-R-Phenylhydrazono)...

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“…26,30 See Supplementary Information for description on the synthesis, analytical and spectroscopic data of the novel products.…”

Section: Synthesis Of the Hydrazono Compounds Hl1-hl13mentioning

confidence: 99%

“…26,27 Complexes 1-13 ( Figure 3) were obtained by addition of triethylamine to a methanol suspension of HLn (n = 1-13) and CuCl 2…”

Section: Synthesis and Characterization Of The Copper(ii) Complexesmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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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

Francisco

Vargas

Fragoso

et al. 2010

J. Braz. Chem. Soc.

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Role of Metallodrugs in Medicinal Inorganic Chemistry

Kumar

Kant

et al. 2020

Advances in Metallodrugs

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Synthesis, characterization, molecular docking, biological activity and density functional theory studies of novel 1,4‐naphthoquinone derivatives and Pd(II), Ni(II) and Co(II) complexes

Ekennia

Osowole

Onwudiwe

et al. 2018

Applied Organom Chemis

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Two novel heterocyclic ligands, 2-[(5-fluoro-1,3-benzothiazol-2-yl)amino]naphthalene-1,4-dione (HL 1 ) and 2-[(5-methyl-1,3-benzothiazol-2-yl)amino]naphthalene-1,4-dione (HL 2 ), and their Pd(II), Ni(II) and Co(II) complexes were prepared and characterized using 1 H NMR, 13 C NMR, infrared and UV-visible spectroscopic techniques, elemental analysis, magnetic susceptibility, thermogravimetry and molar conductance measurements. The infrared spectral data showed that the chelation behaviours of the ligands towards the transition metal ions were through one of the carbonyl oxygen and deprotonated nitrogen atom of the secondary amine group. Molar conductance results confirmed that the complexes are non-electrolytes in dimethylsulfoxide. The geometries of the complexes were deduced from magnetic susceptibility and UV-visible spectroscopic results. Second-order perturbation analysis using density functional theory calculation revealed a stronger intermolecular charge transfer between ligand and metal ion in [NiL 1 (H 2 O) 2 (CH 3 COO-)] and CoL 1 compared to the other complexes. The in vitro antibacterial activity of the compounds against some clinically isolated bacteria strains showed varied activities. [NiL 1 (H 2 O) 2 (CH 3 COO-)] exhibited the best antibacterial results with a minimum inhibitory concentration of 50 μg mL −1 . The molecular interactions of the compounds with various drug targets of some bacterial organisms were established in a bid to predict the possible mode of antibacterial action of the compounds. The ferrous ion chelating ability of the

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Hydroxynaphthoquinone Metal Complexes as Antitumor Agents X: Synthesis, Structure, Spectroscopy and In Vitro Antitumor Activity of 3‐Methyl‐Phenylazo Lawsone Derivatives and Their Metal Complexes Against Human Breast Cancer Cell Line MCF‐7

Cited by 31 publications

References 0 publications

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

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

Role of Metallodrugs in Medicinal Inorganic Chemistry

Synthesis, characterization, molecular docking, biological activity and density functional theory studies of novel 1,4‐naphthoquinone derivatives and Pd(II), Ni(II) and Co(II) complexes

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