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Romanyuk, A. L.; Polishchuk, O. P.; Litvin, B. L.; Ganushchak, N. I.

doi:10.1023/a:1015429803432

Cited by 11 publications

(12 citation statements)

References 2 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%

“…26,27,30,31 HL1, HL7, HL11, HL12 and HL13 were described previously. 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%

“…Low solubility prevented experimental NMR experiments. 25 Some of these compounds have been previously described, 26,27,30,31 but their tautomerism has not yet been investigated. In addition to reporting the synthesis of novel compounds (HL1-HL13), we also present the results of in vitro antitumor screening and antibacterial activity of these compounds and of their copper(II) complexes (Scheme 1) against several cancer cell lines (SF-295, HCT-8, MDAMB-435 and HL-60) and bacteria strains (…”

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%

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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%

Section: Synthesis Of the Hydrazono Compounds Hl1-hl13mentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

mentioning

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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“…8,9 Both routes start from 3-(4 -nitrophenylazo)-4-hydroxy-1,2-naphthoquinone (1) which was prepared from the coupling reaction of the diazonium salt of 4-nitroaniline with 2-hydroxy-1,4-naphthoquinone in basic medium, as described in the literature. 10 The product precipitates immediately and is obtained in a pure form in 92% yield. It is poorly soluble in usual organic solvents.…”

Section: New Synthetic Routes For the Preparation Of 2-amino-3-hydroxmentioning

confidence: 99%

New Synthetic Routes for the Preparation of 2-Amino-3-hydroxy-1,4-naphthoquinone

Francisco

Casellato

Vargas

2009

Organic Preparations and Procedures International

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Azo Appended Modified Lawsone Derived Ru‐Systems with Multi‐Redox Entities. Competitive Electronic Form and the Question of Azo Reduction

Arya

Bera

Lahiri

2023

Chemistry A European J

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The article dealt with the ruthenium complexes of redox active azo appended modified lawsone L 1 À (HL 1 : (E)-2hydroxy-3-(p-tolyldiazenyl)naphthalene-1,4-dione))/L 2 À (HL 2 :5-À and L 2 À differed with respect to the para-quinone versus phenazine moieties linked to the azo function. Structural analysis of the complexes established unreduced state of the azo (N=N) group of coordinated L 1 À /L 2 À or pap as well as unprecedented para-quinone form of L 1 À . The involvement of selective redox center(s) towards the accessible redox steps of the complexes encompassing multiple redox active entities i. e. Ru, phenolate (L 1 À /L 2 À ), para-quinone (L 1 À ), phenazine (L 2 À ), azo (L 1 À /L 2 À , pap), diimine (bpy) was analyzed by combined experimental and DFT calculations. It revealed that under the prevailing competitive scenario oxidation was mostly dominated by the phenolate group of L 1 À /L 2 À (phenolate!phenoxide), while successive reductions were taken place either at the para-quinone/phenazine units of L 1 À /L 2 À or azo/diimine functions of pap/bpy. Though the azo function of pap in 3 + /7 + underwent facile reduction, the same azo function associated with L 1 À /L 2 À conspicuously remained unreduced in all occasions. The frontier molecular orbital analysis revealed that the propensity of pap for the azo reduction with special reference to that in L 1 À /L 2 À could be correlated with its relatively lower energy π* orbital (LUMO). Complexes displayed intense LMCT (1/5) and bpy (2 + /6 + ), pap (3 + /7 + ), L (4/8) targeted MLCT transitions in the visible region.

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Cited by 11 publications

References 2 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

New Synthetic Routes for the Preparation of 2-Amino-3-hydroxy-1,4-naphthoquinone

Azo Appended Modified Lawsone Derived Ru‐Systems with Multi‐Redox Entities. Competitive Electronic Form and the Question of Azo Reduction

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