Sixteen novel 6- and 2-(1-acylsulfanylalkyl)-5,8-dimethoxy-l,4-naphthoquinones were designed and synthesized. Their cytotoxicities were evaluated in vitro against BEL-7402, HT-29 and SPC-Al cell lines. The pharmacol...Sixteen novel 6- and 2-(1-acylsulfanylalkyl)-5,8-dimethoxy-l,4-naphthoquinones were designed and synthesized. Their cytotoxicities were evaluated in vitro against BEL-7402, HT-29 and SPC-Al cell lines. The pharmacological results showed that most of the prepared compounds displayed the excellent selectivity for HT-29 cell line. Compound lab exhibited the most potent antitumor activity among the tested compounds.展开更多
<div style="text-align:justify;"> <span style="font-family:Verdana;">The aim of this work is to synthesize, characterize and evaluate the biological activity of 1,4-naphthoquinone deriv...<div style="text-align:justify;"> <span style="font-family:Verdana;">The aim of this work is to synthesize, characterize and evaluate the biological activity of 1,4-naphthoquinone derivatives ligands and their metal—Co(II), Ni(II) and Cu(II) chelates. Continuing our work with another derivatives of 1,4-naphthoquinone ligands, this work had been constructed for synthesis of new ligands derived from 1,4-naphthoquinone such as 3-thioacetyl-2-amino-1,4-naphthoquinone and 2-benzoyl-3-amino-1,4-naphthoquinone (L<span style="white-space:nowrap;"><sup>1</sup></span>-L<span style="white-space:nowrap;"><sup>2</sup></span>) which characterized on the basis of elemental analysis, electronic, IR, mass, <span style="white-space:nowrap;"><sup>1</sup></span>H-NMR spectral data. The synthesized ligands have been carried out to achieve the coordination behavior towards bi-valent metal ions like cobalt, nickel and copper. The solid chelates of the different ligands were prepared and subjected to analytical techniques such as elemental analyses, spectroscopic techniques including mass, <span style="white-space:nowrap;"><sup>1</sup></span>H-NMR, and IR spectroscopy, and thermal analyses techniques. The chelates were found to have octahedral geometry. The biological activity of the prepared ligands and their binary metals complexes were also screened against different antifungal and antibacterial organisms.</span> </div>展开更多
<div style="text-align:justify;"> <span style="font-family:Verdana;">The aim of this work is to synthesize, characterize and evaluate the biological activity of 2-acetyl and 2-formyl-3-...<div style="text-align:justify;"> <span style="font-family:Verdana;">The aim of this work is to synthesize, characterize and evaluate the biological activity of 2-acetyl and 2-formyl-3-amino-1,4-naphthoquinone (L<span style="white-space:nowrap;"><sup>1</sup></span> - L<span style="white-space:nowrap;"><sup>2</sup></span>) and their metal-Co(II), Ni(II) and Cu(II) chelates. The newly chelates were characterized by elemental analysis, IR, mass and <span style="white-space:nowrap;"><sup>1</sup></span>HNMR spectra, thermogravimetric analysis (TGA) and biological activity. The antibacterial and antifungal activities of the ligands and its metal complexes were screened against bacterial species (<span style="white-space:nowrap;"><i>Staphylococcus aureus, Bacillus subtilis and Escherichia coli</i></span>) and fungi (<span style="white-space:nowrap;"><i>Candida albicans</i></span>). Ampicillin and amphotericin were used as references for antibacterial and antifungal studies. The activity data show that the metal complexes have a promising biological activity comparable with parent free ligand against bacterial and fungal species.</span> </div>展开更多
In an alkaline 2-propanol solution with 5,10,15,20-tetra(4-methoxyl phenyl) porphyrin iron chloride(TOMPPFeCl) as a catalyst and oxygen as a cheap green oxidant, 2-naphthol was conversed to 2-hydroxy-\{1,4-naphthoquin...In an alkaline 2-propanol solution with 5,10,15,20-tetra(4-methoxyl phenyl) porphyrin iron chloride(TOMPPFeCl) as a catalyst and oxygen as a cheap green oxidant, 2-naphthol was conversed to 2-hydroxy-\{1,4-naphthoquinone(HNQ)\} with a yield of 62.17% and a selectivity of 100%, and the conversion number of TMOPPFeCl catalyst was 8.32/min. The catalytic oxidation products were characterized by means of UV-Vis, IR, GC-MS, ~ 1H NMR and melting point determination. In this catalytic oxidation, the catalytic activity of TMOPPFeCl was researched in detail and the reacting conditions were optimized. A possible reaction mechanism is summarized based on in situ EPR determination.展开更多
The diverse and large-scale application of disinfectants posed potential health risks and caused ecological damage during the 2019-nCoV pandemic,thereby increasing the demands for the development of disinfectants base...The diverse and large-scale application of disinfectants posed potential health risks and caused ecological damage during the 2019-nCoV pandemic,thereby increasing the demands for the development of disinfectants based on natural products,with low health risks and low aquatic toxicity.In the present study,a few natural naphthoquinones and their derivatives bearing the 1,4-naphthoquinone skeleton were synthesized,and their antibacterial activity against selected bacterial strains was evaluated.In vitro antibacterial activities of the compounds were investigated against Escherichia coli and Staphylococcus aureus.Under the minimum inhibitory concentration(MIC)of≤0.125μmol/L for juglone(1a),5,8-dimethoxy-1,4-naphthoquinone(1f),and 7-methyl-5-acetoxy-1,4-naphthoquinone(3),a strong antibacterial activity against S.aureus was observed.All 1,4-naphthoquinone derivatives exhibited a strong antibacterial activity,with MIC values ranging between 15.625 and 500μmol/Land ECso values rangingbetween10.56 and248.42μmol/L.Most of the synthesized compounds exhibited strong antibacterial activities against S.aureus.Among these compounds,juglone(la)showed the strongest antibacterial activity.The results from mechanistic investigations indicated that juglone,a natural naphthoquinone,caused cell death by inducing reactive oxygen species production in bacterial cells,leading to DNA damage.In addition,juglone could reduce the self-repair ability of bacterial DNA by inhibiting RecA expression.In addition to having a potent antibacterial activity,juglone exhibited low cytotoxicity in cell-based investigations.In conclusion,juglone is a strong antibacterial agent with low toxicity,indicating that its application as a bactericidal agent may be associated with low health risks and aquatic toxicity.展开更多
文摘Sixteen novel 6- and 2-(1-acylsulfanylalkyl)-5,8-dimethoxy-l,4-naphthoquinones were designed and synthesized. Their cytotoxicities were evaluated in vitro against BEL-7402, HT-29 and SPC-Al cell lines. The pharmacological results showed that most of the prepared compounds displayed the excellent selectivity for HT-29 cell line. Compound lab exhibited the most potent antitumor activity among the tested compounds.
文摘<div style="text-align:justify;"> <span style="font-family:Verdana;">The aim of this work is to synthesize, characterize and evaluate the biological activity of 1,4-naphthoquinone derivatives ligands and their metal—Co(II), Ni(II) and Cu(II) chelates. Continuing our work with another derivatives of 1,4-naphthoquinone ligands, this work had been constructed for synthesis of new ligands derived from 1,4-naphthoquinone such as 3-thioacetyl-2-amino-1,4-naphthoquinone and 2-benzoyl-3-amino-1,4-naphthoquinone (L<span style="white-space:nowrap;"><sup>1</sup></span>-L<span style="white-space:nowrap;"><sup>2</sup></span>) which characterized on the basis of elemental analysis, electronic, IR, mass, <span style="white-space:nowrap;"><sup>1</sup></span>H-NMR spectral data. The synthesized ligands have been carried out to achieve the coordination behavior towards bi-valent metal ions like cobalt, nickel and copper. The solid chelates of the different ligands were prepared and subjected to analytical techniques such as elemental analyses, spectroscopic techniques including mass, <span style="white-space:nowrap;"><sup>1</sup></span>H-NMR, and IR spectroscopy, and thermal analyses techniques. The chelates were found to have octahedral geometry. The biological activity of the prepared ligands and their binary metals complexes were also screened against different antifungal and antibacterial organisms.</span> </div>
文摘<div style="text-align:justify;"> <span style="font-family:Verdana;">The aim of this work is to synthesize, characterize and evaluate the biological activity of 2-acetyl and 2-formyl-3-amino-1,4-naphthoquinone (L<span style="white-space:nowrap;"><sup>1</sup></span> - L<span style="white-space:nowrap;"><sup>2</sup></span>) and their metal-Co(II), Ni(II) and Cu(II) chelates. The newly chelates were characterized by elemental analysis, IR, mass and <span style="white-space:nowrap;"><sup>1</sup></span>HNMR spectra, thermogravimetric analysis (TGA) and biological activity. The antibacterial and antifungal activities of the ligands and its metal complexes were screened against bacterial species (<span style="white-space:nowrap;"><i>Staphylococcus aureus, Bacillus subtilis and Escherichia coli</i></span>) and fungi (<span style="white-space:nowrap;"><i>Candida albicans</i></span>). Ampicillin and amphotericin were used as references for antibacterial and antifungal studies. The activity data show that the metal complexes have a promising biological activity comparable with parent free ligand against bacterial and fungal species.</span> </div>
文摘In an alkaline 2-propanol solution with 5,10,15,20-tetra(4-methoxyl phenyl) porphyrin iron chloride(TOMPPFeCl) as a catalyst and oxygen as a cheap green oxidant, 2-naphthol was conversed to 2-hydroxy-\{1,4-naphthoquinone(HNQ)\} with a yield of 62.17% and a selectivity of 100%, and the conversion number of TMOPPFeCl catalyst was 8.32/min. The catalytic oxidation products were characterized by means of UV-Vis, IR, GC-MS, ~ 1H NMR and melting point determination. In this catalytic oxidation, the catalytic activity of TMOPPFeCl was researched in detail and the reacting conditions were optimized. A possible reaction mechanism is summarized based on in situ EPR determination.
基金the Startup Fund for Youngman Research at SJTU(No.19X100040082)the Medical and Engineering Interdisciplinary Research Fund of Shanghai Jiao Tong University(No.20X190020002).
文摘The diverse and large-scale application of disinfectants posed potential health risks and caused ecological damage during the 2019-nCoV pandemic,thereby increasing the demands for the development of disinfectants based on natural products,with low health risks and low aquatic toxicity.In the present study,a few natural naphthoquinones and their derivatives bearing the 1,4-naphthoquinone skeleton were synthesized,and their antibacterial activity against selected bacterial strains was evaluated.In vitro antibacterial activities of the compounds were investigated against Escherichia coli and Staphylococcus aureus.Under the minimum inhibitory concentration(MIC)of≤0.125μmol/L for juglone(1a),5,8-dimethoxy-1,4-naphthoquinone(1f),and 7-methyl-5-acetoxy-1,4-naphthoquinone(3),a strong antibacterial activity against S.aureus was observed.All 1,4-naphthoquinone derivatives exhibited a strong antibacterial activity,with MIC values ranging between 15.625 and 500μmol/Land ECso values rangingbetween10.56 and248.42μmol/L.Most of the synthesized compounds exhibited strong antibacterial activities against S.aureus.Among these compounds,juglone(la)showed the strongest antibacterial activity.The results from mechanistic investigations indicated that juglone,a natural naphthoquinone,caused cell death by inducing reactive oxygen species production in bacterial cells,leading to DNA damage.In addition,juglone could reduce the self-repair ability of bacterial DNA by inhibiting RecA expression.In addition to having a potent antibacterial activity,juglone exhibited low cytotoxicity in cell-based investigations.In conclusion,juglone is a strong antibacterial agent with low toxicity,indicating that its application as a bactericidal agent may be associated with low health risks and aquatic toxicity.