A Lewis base catalyzed ring expansion of isatin with 2,2,2-trifluorodiazoethane(CF3 CHN2)is developed.It is characterized that the merge of tetramethylethylenediamine and CF3 CHN2 generates reactive triazene intermedi...A Lewis base catalyzed ring expansion of isatin with 2,2,2-trifluorodiazoethane(CF3 CHN2)is developed.It is characterized that the merge of tetramethylethylenediamine and CF3 CHN2 generates reactive triazene intermediates,which construct substituted 3-hydroxy-4-(trifluoromethyl)quinolinones with high efficiency.Synthetic application of the procedure is broadened by 3-trifluormethylpyrazole fused3-hydroxy-4-(trifluoromethyl)quinolinone synthesis.展开更多
3-(5-(2.4-dichlorophyenyl)-4.5-dihydro-1H-pyrazol-3-yl)-4hydroxy-1-methylquinolin(1H)-one, 5-((4-hydroxy-8-methyl-2-oxo-1.2-dihydroquinolin-3-yl)methylene)-1-phenyl-2-hioxodihydropyrimidine-4.6(1H.5H)-dione, and 1-but...3-(5-(2.4-dichlorophyenyl)-4.5-dihydro-1H-pyrazol-3-yl)-4hydroxy-1-methylquinolin(1H)-one, 5-((4-hydroxy-8-methyl-2-oxo-1.2-dihydroquinolin-3-yl)methylene)-1-phenyl-2-hioxodihydropyrimidine-4.6(1H.5H)-dione, and 1-butyl-4-hydroxy-3-(5-styryl-4.5-dihydro-1H-pyrazol-3yl)quinolin-2(1H)-one were synthesized and characterized by spectroscopy analysis. These compounds are designated I, II and III, respectively. The antioxidants efficiency of the synthesized compounds in lubricating greases had been investigated using ASTM d-942 and ASTM d-664. The obtained data showed that the total acid number and oxygen pressure drop of these compounds in lubricating greases decrease in the order: Comp.III. < Comp.I. < Comp.II. The antioxidant efficiency of the prepared quinolinones derivatives was discussed. Acceptable correlations were obtained between the obtained oxidation inhibition and the calculated quantum chemical parameters.展开更多
Quinolinones have been prepared by an intramolecular radical annulation ofα-EWG(electron-withdrawing group)substituted amides and alkynes involving an electrochemical oxidation enabled hydrogen atom transfer(HAT)path...Quinolinones have been prepared by an intramolecular radical annulation ofα-EWG(electron-withdrawing group)substituted amides and alkynes involving an electrochemical oxidation enabled hydrogen atom transfer(HAT)pathway,with commercially available Cp_(2)Fe as a molecular electrochemical catalyst,thereby eliminating the need for stoichiometric chemical oxidants or reductants.An electrochemically generated carbon radical centered on anα-electron-deficient amide adds to a tethered alkyne followed by HAT and tautomerism,giving a wide variety of quinolinones in high yield,with good functional group compatibility in up to a gram scale under mild conditions.展开更多
SARS CoV 3CL^pro is known to be a promising target for development of therapeutic agents against the severe acute respiratory syndrome （SARS）. A quinolinone compound 1 was selected via virtual screening, and it was ...SARS CoV 3CL^pro is known to be a promising target for development of therapeutic agents against the severe acute respiratory syndrome （SARS）. A quinolinone compound 1 was selected via virtual screening, and it was syn- thetized and tested for enzymatic inhibition in vitro. Compound 1 showed potent inhibitory activity （ICs0= 0.44 μmol/L） toward SARS CoV 3CL^pro. Further work on a series of quinolinone derivatives resulted in the discovery of the most potent compound 23, inhibiting SARS CoV 3CL^pro with an IC50 of 36.86 μmol/L. The structure-activity relationships were also discussed.展开更多
Quinolinone and its derivatives have been known as growth hormones, antibiotics, fragrance, fluorescent materials, etc. Although various photochemical behavior including photodimerization, photocycloaddition and photo...Quinolinone and its derivatives have been known as growth hormones, antibiotics, fragrance, fluorescent materials, etc. Although various photochemical behavior including photodimerization, photocycloaddition and photoprenylation has been reported, little展开更多
基金financial support from the National Natural Science Foundation of China(No.81602977)the CAMS Innovation Fund for Medical Sciences(Nos.2019-RC-HL-010,2017-I2M-1013)+1 种基金the Science and Technology Development Project of Jilin Province of China(No.20190304050YY)China Association of Chinese Medicine(No.2017QNRC001)。
文摘A Lewis base catalyzed ring expansion of isatin with 2,2,2-trifluorodiazoethane(CF3 CHN2)is developed.It is characterized that the merge of tetramethylethylenediamine and CF3 CHN2 generates reactive triazene intermediates,which construct substituted 3-hydroxy-4-(trifluoromethyl)quinolinones with high efficiency.Synthetic application of the procedure is broadened by 3-trifluormethylpyrazole fused3-hydroxy-4-(trifluoromethyl)quinolinone synthesis.
文摘3-(5-(2.4-dichlorophyenyl)-4.5-dihydro-1H-pyrazol-3-yl)-4hydroxy-1-methylquinolin(1H)-one, 5-((4-hydroxy-8-methyl-2-oxo-1.2-dihydroquinolin-3-yl)methylene)-1-phenyl-2-hioxodihydropyrimidine-4.6(1H.5H)-dione, and 1-butyl-4-hydroxy-3-(5-styryl-4.5-dihydro-1H-pyrazol-3yl)quinolin-2(1H)-one were synthesized and characterized by spectroscopy analysis. These compounds are designated I, II and III, respectively. The antioxidants efficiency of the synthesized compounds in lubricating greases had been investigated using ASTM d-942 and ASTM d-664. The obtained data showed that the total acid number and oxygen pressure drop of these compounds in lubricating greases decrease in the order: Comp.III. < Comp.I. < Comp.II. The antioxidant efficiency of the prepared quinolinones derivatives was discussed. Acceptable correlations were obtained between the obtained oxidation inhibition and the calculated quantum chemical parameters.
基金support from the Natural Science Project of the Jiangsu Higher Education Institutions(No.24KJB150034)the Large Scientific Instruments Open to Share Independent Research Project of Jiangsu Province(No.TC2023A044)Yancheng Teachers University.
文摘Quinolinones have been prepared by an intramolecular radical annulation ofα-EWG(electron-withdrawing group)substituted amides and alkynes involving an electrochemical oxidation enabled hydrogen atom transfer(HAT)pathway,with commercially available Cp_(2)Fe as a molecular electrochemical catalyst,thereby eliminating the need for stoichiometric chemical oxidants or reductants.An electrochemically generated carbon radical centered on anα-electron-deficient amide adds to a tethered alkyne followed by HAT and tautomerism,giving a wide variety of quinolinones in high yield,with good functional group compatibility in up to a gram scale under mild conditions.
文摘SARS CoV 3CL^pro is known to be a promising target for development of therapeutic agents against the severe acute respiratory syndrome （SARS）. A quinolinone compound 1 was selected via virtual screening, and it was syn- thetized and tested for enzymatic inhibition in vitro. Compound 1 showed potent inhibitory activity （ICs0= 0.44 μmol/L） toward SARS CoV 3CL^pro. Further work on a series of quinolinone derivatives resulted in the discovery of the most potent compound 23, inhibiting SARS CoV 3CL^pro with an IC50 of 36.86 μmol/L. The structure-activity relationships were also discussed.
文摘Quinolinone and its derivatives have been known as growth hormones, antibiotics, fragrance, fluorescent materials, etc. Although various photochemical behavior including photodimerization, photocycloaddition and photoprenylation has been reported, little
