Background and Objective: Pyrazolone derivatives were reported to have a potent cytotoxicity against some tumor cells. In the present study, we evaluated the cytotoxic activity of a series of pyrazolone derivatives ag...Background and Objective: Pyrazolone derivatives were reported to have a potent cytotoxicity against some tumor cells. In the present study, we evaluated the cytotoxic activity of a series of pyrazolone derivatives against four human tumor cell lines including HepG2, OVCAR3, KB, and multidrug resistance (MDR) KBv200 cell lines in vitro and in vivo. Additionally, the structure-activity relationships of these compounds were discussed. Methods: To analyze the antiproliferative potential of the synthesized compounds against several human tumor cell lines, the 50% inhibitory concentration (IC50) values were determined by MTT assay. Besides, the KBv200 cell xenograft experimental model was established and the sensitivity to the pyrazolone compounds was compared between drug-sensitive parental KB cells and MDR KBv200 cells. Results: Of 13 compounds screened, compound 9 presented remarkable anticancer effects, of which IC50 values were (3.24 ± 0.28), (2.58 ± 0.61), (3.81 ± 0.02), and (3.45 ± 0.03) μg/mL in HepG2, OVCAR3, KB and MDR KBv200 cells, respectively (P > 0.05). Furthermore, compound 9 effectively inhibited tumor growth of KBv200 cell xenografts in vivo, the inhibition ratio was 25.37%, 38.43%, and 47.50% for 1.5 mg/kg, 3 mg/kg, and 6 mg/kg of compound 9 groups, respectively. Conclusion: Compound 9 was the most promising antitumor agent in this study.展开更多
A convenient,economical and green approach to the synthesis of 1H-indazolo[1,2-b]phthalazine-1,6,11-trione derivatives has been achieved via a one-pot protocol using phthalhydrazide,a cyclic-β-diketone and an aldehyd...A convenient,economical and green approach to the synthesis of 1H-indazolo[1,2-b]phthalazine-1,6,11-trione derivatives has been achieved via a one-pot protocol using phthalhydrazide,a cyclic-β-diketone and an aldehyde in the presence of a ceric ammonium nitrate catalyst in polyethylene glycol.The simple work up,mild conditions,excellent yields,inexpensive and non-toxic catalyst and simple solvent recyclability render this protocol both attractive and economically viable.展开更多
To evaluate the stability of N-alkylated pyrrolidone derivatives （NRPs）, which are supposed to be used as precipitants for U（VI） and Pu（IV, VI） species in HNO3 media, under irradiation environment, some candidat...To evaluate the stability of N-alkylated pyrrolidone derivatives （NRPs）, which are supposed to be used as precipitants for U（VI） and Pu（IV, VI） species in HNO3 media, under irradiation environment, some candidate NRPs were irradiated by γ-ray. Irradia- tion to HNO3 solutions up to 6 mol dm-3 （= M） containing 2 M N-n-butyl-2-pyrrolidone （NBP）, one of NRPs with lower hy- drophobicity, has revealed that the residual ratios of NBP in the samples of HNO3 up to 3 M decreased identically and linearly. Approximately 20% of NBP was found to be degraded after the irradiation at 1 MGy. It was also found that the decrease in the precipitation ratio of UOf＋ （P.R., %） was gentle and that the P.R. values were relatively in accordance with the residual ratios of NBP. On the other hand, the degradation of the samples irradiated in 6 M HNO3 was found more distinguished. It was pro- posed from the analyses of degraded compounds that the degradation of NBP in HNO3 by γ-ray irradiation started from the cleavage of the pyrrolidone ring by the addition of oxygen atom originating from HNO3, followed by the formation of chain compounds by the successive addition of oxygen, leading to the generation of oxalic acid and acetic acid. The stability of other NRPs in 3 M HNO3 was evaluated to be nearly identical with that of NBP except lower P.R. values of the samples containing NRPs with higher hydrophobicity irradiated at more than 0.5 MGy.展开更多
An efficient one-pot procedure for the synthesis of multisubstituted xanthone derivatives using Fe-catalyzed reactions of 2-aryloxybenzaldehydes followed by DDQ(2,3-dichloro-5,6-dicyano-1,4-benzoquinone) oxidation has...An efficient one-pot procedure for the synthesis of multisubstituted xanthone derivatives using Fe-catalyzed reactions of 2-aryloxybenzaldehydes followed by DDQ(2,3-dichloro-5,6-dicyano-1,4-benzoquinone) oxidation has been developed.This method offers a convenient high-yield route to xanthones from easily accessible starting materials.展开更多
复配杀菌剂已大量商品化，其主要优点在于可以扩大单一品种的杀菌谱及延迟个别组份的抗性发展。由于复配杀菌剂也表现出了协同灭菌作用，因此可减少其活性成分的使用量。现已发现苯甲酮衍生物具有杀菌活性，Bakana等人已经从生长于扎伊...复配杀菌剂已大量商品化，其主要优点在于可以扩大单一品种的杀菌谱及延迟个别组份的抗性发展。由于复配杀菌剂也表现出了协同灭菌作用，因此可减少其活性成分的使用量。现已发现苯甲酮衍生物具有杀菌活性，Bakana等人已经从生长于扎伊尔的藤黄(Garcinia huillensis Wellw ex Oliv)茎干背部分离出苯甲酮类似物并将其用于中非传统医学，展开更多
A simple and efficient method for the synthesis of 9,9‐dimethyl‐9,10‐dihydro‐8H‐benzo‐[α]xanthen‐11(12)‐one derivatives (DDBXs) was developed by the condensation reaction of various substituted aryl aldehydes...A simple and efficient method for the synthesis of 9,9‐dimethyl‐9,10‐dihydro‐8H‐benzo‐[α]xanthen‐11(12)‐one derivatives (DDBXs) was developed by the condensation reaction of various substituted aryl aldehydes with 2‐naphthol and dimedone using Fe3O4 magnetic nanoparticles (MNPs) as a heterogeneous catalyst under solvent‐free conditions at 90–110 °C.The experimental procedure is very simple,the products are formed in high yields and the catalyst is easily separated by applying an external magnetic field.展开更多
A simple and convenient approach for the synthesis of tetraheterocyclic benzothiazolo-[2,3-b]-quinazolin-1-ones has been developed utilizing the MCR methodology, which involves the condensation of 2-aminobenzothiazole...A simple and convenient approach for the synthesis of tetraheterocyclic benzothiazolo-[2,3-b]-quinazolin-1-ones has been developed utilizing the MCR methodology, which involves the condensation of 2-aminobenzothiazole, cyclic-diketones and various aldehydes using Amberlyst-15 in PEG 400 as an environmentally benign and reusable catalyst system. Environmental benignity, recyclability, cost-effectiveness, easy workup and excellent yields are the major attributes of this one-pot procedure.展开更多
A series of compounds containing the 1H-pyrazino[1,2-a]quinoxaline-1,5(6H)-dione scaffold have been synthesized using a one-pot procedure under microwave irradiation. This new strategy allowed for the facile synthesis...A series of compounds containing the 1H-pyrazino[1,2-a]quinoxaline-1,5(6H)-dione scaffold have been synthesized using a one-pot procedure under microwave irradiation. This new strategy allowed for the facile synthesis of target compounds in good yields and could be readily applied to the construction of diverse libraries of compounds for high throughput screening in medicinal chemistry.展开更多
The structure and electronic properties of a series of biologically active dithiolethiones （1） have been calculated using semi-empirical. Multi-linear regression analysis suggests that there is a reasonable correlat...The structure and electronic properties of a series of biologically active dithiolethiones （1） have been calculated using semi-empirical. Multi-linear regression analysis suggests that there is a reasonable correlation between the experimental activity of the derivatives against chelation activity and calculated properties such as the HOMO energies, molar refractivity, dipole moments and experimental partition coefficient. From the derived QSAR equations the 3-Methylthio-4p-Tolyle-1,2-Dithiolylium accompanying ion （CH3SO4） and 4-para-tolyl-1,2-dithiole-3-thione （2b and 2） are predicted to show the highest activity against chelation activity, while 3-Methylthio-5p-methoxy phenyl-1,2-Dithiolylium accompanying ion （I-） （3a） is predicted to be the least active in line with the experimental results.展开更多
7‐Aryl‐8H‐benzo[f]indeno[2,1‐b]quinoline‐8‐one derivatives were synthesized by means of a one‐pot condensation of 2‐naphthylamine, aromatic aldehydes, and indane‐1,3‐dione in ethanol under refluxing conditio...7‐Aryl‐8H‐benzo[f]indeno[2,1‐b]quinoline‐8‐one derivatives were synthesized by means of a one‐pot condensation of 2‐naphthylamine, aromatic aldehydes, and indane‐1,3‐dione in ethanol under refluxing conditions in the presence of poly(4‐vinylpyridinium) hydrogen sulfate, a solid acid catalyst. This method has the advantages of high yield, clean reaction, simple methodology, and short reaction time. The catalyst could be recycled and reused four times without significant loss of activity. The structure of the novel compounds was confirmed by IR, 1H NMR, and 13C NMR spec-troscopy and elemental analysis.展开更多
基金National Sciences Foundation (No. 30672407)Key Science and Technology Foundation of Guangdong Province (No. 2004B30101005)No.985-II foundation of State Key Laboratory of Oncology in South China
文摘Background and Objective: Pyrazolone derivatives were reported to have a potent cytotoxicity against some tumor cells. In the present study, we evaluated the cytotoxic activity of a series of pyrazolone derivatives against four human tumor cell lines including HepG2, OVCAR3, KB, and multidrug resistance (MDR) KBv200 cell lines in vitro and in vivo. Additionally, the structure-activity relationships of these compounds were discussed. Methods: To analyze the antiproliferative potential of the synthesized compounds against several human tumor cell lines, the 50% inhibitory concentration (IC50) values were determined by MTT assay. Besides, the KBv200 cell xenograft experimental model was established and the sensitivity to the pyrazolone compounds was compared between drug-sensitive parental KB cells and MDR KBv200 cells. Results: Of 13 compounds screened, compound 9 presented remarkable anticancer effects, of which IC50 values were (3.24 ± 0.28), (2.58 ± 0.61), (3.81 ± 0.02), and (3.45 ± 0.03) μg/mL in HepG2, OVCAR3, KB and MDR KBv200 cells, respectively (P > 0.05). Furthermore, compound 9 effectively inhibited tumor growth of KBv200 cell xenografts in vivo, the inhibition ratio was 25.37%, 38.43%, and 47.50% for 1.5 mg/kg, 3 mg/kg, and 6 mg/kg of compound 9 groups, respectively. Conclusion: Compound 9 was the most promising antitumor agent in this study.
文摘A convenient,economical and green approach to the synthesis of 1H-indazolo[1,2-b]phthalazine-1,6,11-trione derivatives has been achieved via a one-pot protocol using phthalhydrazide,a cyclic-β-diketone and an aldehyde in the presence of a ceric ammonium nitrate catalyst in polyethylene glycol.The simple work up,mild conditions,excellent yields,inexpensive and non-toxic catalyst and simple solvent recyclability render this protocol both attractive and economically viable.
文摘To evaluate the stability of N-alkylated pyrrolidone derivatives （NRPs）, which are supposed to be used as precipitants for U（VI） and Pu（IV, VI） species in HNO3 media, under irradiation environment, some candidate NRPs were irradiated by γ-ray. Irradia- tion to HNO3 solutions up to 6 mol dm-3 （= M） containing 2 M N-n-butyl-2-pyrrolidone （NBP）, one of NRPs with lower hy- drophobicity, has revealed that the residual ratios of NBP in the samples of HNO3 up to 3 M decreased identically and linearly. Approximately 20% of NBP was found to be degraded after the irradiation at 1 MGy. It was also found that the decrease in the precipitation ratio of UOf＋ （P.R., %） was gentle and that the P.R. values were relatively in accordance with the residual ratios of NBP. On the other hand, the degradation of the samples irradiated in 6 M HNO3 was found more distinguished. It was pro- posed from the analyses of degraded compounds that the degradation of NBP in HNO3 by γ-ray irradiation started from the cleavage of the pyrrolidone ring by the addition of oxygen atom originating from HNO3, followed by the formation of chain compounds by the successive addition of oxygen, leading to the generation of oxalic acid and acetic acid. The stability of other NRPs in 3 M HNO3 was evaluated to be nearly identical with that of NBP except lower P.R. values of the samples containing NRPs with higher hydrophobicity irradiated at more than 0.5 MGy.
基金supported by the National Natural Science Foundation of China (20872037)
文摘An efficient one-pot procedure for the synthesis of multisubstituted xanthone derivatives using Fe-catalyzed reactions of 2-aryloxybenzaldehydes followed by DDQ(2,3-dichloro-5,6-dicyano-1,4-benzoquinone) oxidation has been developed.This method offers a convenient high-yield route to xanthones from easily accessible starting materials.
文摘复配杀菌剂已大量商品化，其主要优点在于可以扩大单一品种的杀菌谱及延迟个别组份的抗性发展。由于复配杀菌剂也表现出了协同灭菌作用，因此可减少其活性成分的使用量。现已发现苯甲酮衍生物具有杀菌活性，Bakana等人已经从生长于扎伊尔的藤黄(Garcinia huillensis Wellw ex Oliv)茎干背部分离出苯甲酮类似物并将其用于中非传统医学，
基金supported by the Bu‐Ali Sina University,Hamedan 6517838683,Iran
文摘A simple and efficient method for the synthesis of 9,9‐dimethyl‐9,10‐dihydro‐8H‐benzo‐[α]xanthen‐11(12)‐one derivatives (DDBXs) was developed by the condensation reaction of various substituted aryl aldehydes with 2‐naphthol and dimedone using Fe3O4 magnetic nanoparticles (MNPs) as a heterogeneous catalyst under solvent‐free conditions at 90–110 °C.The experimental procedure is very simple,the products are formed in high yields and the catalyst is easily separated by applying an external magnetic field.
文摘A simple and convenient approach for the synthesis of tetraheterocyclic benzothiazolo-[2,3-b]-quinazolin-1-ones has been developed utilizing the MCR methodology, which involves the condensation of 2-aminobenzothiazole, cyclic-diketones and various aldehydes using Amberlyst-15 in PEG 400 as an environmentally benign and reusable catalyst system. Environmental benignity, recyclability, cost-effectiveness, easy workup and excellent yields are the major attributes of this one-pot procedure.
基金supported by the Scientific Research Foundation of Chongqing University of Arts and Sciences(R2013XY01,R2013XY02)the Chongqing Science and Technology Commission(CSTC2013JCYJA50028)SRF for ROCS,SEM
文摘A series of compounds containing the 1H-pyrazino[1,2-a]quinoxaline-1,5(6H)-dione scaffold have been synthesized using a one-pot procedure under microwave irradiation. This new strategy allowed for the facile synthesis of target compounds in good yields and could be readily applied to the construction of diverse libraries of compounds for high throughput screening in medicinal chemistry.
文摘The structure and electronic properties of a series of biologically active dithiolethiones （1） have been calculated using semi-empirical. Multi-linear regression analysis suggests that there is a reasonable correlation between the experimental activity of the derivatives against chelation activity and calculated properties such as the HOMO energies, molar refractivity, dipole moments and experimental partition coefficient. From the derived QSAR equations the 3-Methylthio-4p-Tolyle-1,2-Dithiolylium accompanying ion （CH3SO4） and 4-para-tolyl-1,2-dithiole-3-thione （2b and 2） are predicted to show the highest activity against chelation activity, while 3-Methylthio-5p-methoxy phenyl-1,2-Dithiolylium accompanying ion （I-） （3a） is predicted to be the least active in line with the experimental results.
文摘7‐Aryl‐8H‐benzo[f]indeno[2,1‐b]quinoline‐8‐one derivatives were synthesized by means of a one‐pot condensation of 2‐naphthylamine, aromatic aldehydes, and indane‐1,3‐dione in ethanol under refluxing conditions in the presence of poly(4‐vinylpyridinium) hydrogen sulfate, a solid acid catalyst. This method has the advantages of high yield, clean reaction, simple methodology, and short reaction time. The catalyst could be recycled and reused four times without significant loss of activity. The structure of the novel compounds was confirmed by IR, 1H NMR, and 13C NMR spec-troscopy and elemental analysis.
