A novel approach to the synthesis of 6, 7-disubstituted-1H-quinoxalin-2-ones is described.The title compounds were regioselectively prepared by starting from substituted phenylamines andchloroacetyl chloride through t...A novel approach to the synthesis of 6, 7-disubstituted-1H-quinoxalin-2-ones is described.The title compounds were regioselectively prepared by starting from substituted phenylamines andchloroacetyl chloride through the efficient sequence of acylation, nitration, reduction, intramolecular alkylation, and oxidation.展开更多
A novel series of compounds combining indolin-2-one and quinazolin-4（3H）-one moiety via a carbon-carbon double bond were synthesized by aldol-condensation of 2-methylquinazolin-4（3H）-one-6-carbaldehyde with variou...A novel series of compounds combining indolin-2-one and quinazolin-4（3H）-one moiety via a carbon-carbon double bond were synthesized by aldol-condensation of 2-methylquinazolin-4（3H）-one-6-carbaldehyde with various indolin-2-ones. The synthesized compounds were evaluated for their cytotoxic activity against five human cancer cell lines, namely, A549, MCF-7, HeLa, HT-29 and HCT-116. We found that compound 5e with two bromine atoms at the 5- and 7-positions of the indolin-2-one ring was most potent, which inhibited proliferation of five cancer cell lines in the range of 32.0%-62.3% at a concentration of 50 p,M. Our results further indicate that the connection of 5,7-dibromoindolin-2-one and 2-methylquinazolin- 4（3H）-one moiety with a carbon-carbon double bond is essential for compound 5e to exert cytotoxicity.展开更多
The first HFIP-promoted catalyst-free cascade reactions for the synthesis of biologically relevant 3,3-di(indolyl)indolin-2-ones(27 examples,up to 98% yield) from readily available indoles and isatin derivatives are d...The first HFIP-promoted catalyst-free cascade reactions for the synthesis of biologically relevant 3,3-di(indolyl)indolin-2-ones(27 examples,up to 98% yield) from readily available indoles and isatin derivatives are described.This protocol shows well tolerance of different functional groups and features mild reaction conditions such as short reaction time(~1 h),no usage of catalyst,easy operation and product isolation.Of particular intere st is the formation of two C-C bonds and one all-carbon quaternary center.This protocol could serve as an alternative strategy to synthesize biologically important 3,3-di(indolyl)indolin-2-ones for biological testing.展开更多
文摘A novel approach to the synthesis of 6, 7-disubstituted-1H-quinoxalin-2-ones is described.The title compounds were regioselectively prepared by starting from substituted phenylamines andchloroacetyl chloride through the efficient sequence of acylation, nitration, reduction, intramolecular alkylation, and oxidation.
基金National Natural Science Foundation of China (Grant No.20972099,31130017)Beijing Municipal Commission of Education (Grant No.KZ201210028035)+1 种基金Scientific Research Base Development Program of the Beijing Municipal Commission of Educationthe 973 Project (Grant No.2013CB911000)
文摘A novel series of compounds combining indolin-2-one and quinazolin-4（3H）-one moiety via a carbon-carbon double bond were synthesized by aldol-condensation of 2-methylquinazolin-4（3H）-one-6-carbaldehyde with various indolin-2-ones. The synthesized compounds were evaluated for their cytotoxic activity against five human cancer cell lines, namely, A549, MCF-7, HeLa, HT-29 and HCT-116. We found that compound 5e with two bromine atoms at the 5- and 7-positions of the indolin-2-one ring was most potent, which inhibited proliferation of five cancer cell lines in the range of 32.0%-62.3% at a concentration of 50 p,M. Our results further indicate that the connection of 5,7-dibromoindolin-2-one and 2-methylquinazolin- 4（3H）-one moiety with a carbon-carbon double bond is essential for compound 5e to exert cytotoxicity.
基金supported by the National Natural Science Foundation of China(Nos.81773562,81703326 and 81973177)The Open Project of State Key Laboratory of Natural Medicines(No.SKLNMKF202005)China Postdoctoral Science Foundation(Nos.2018M630840 and 2019T120641)。
文摘The first HFIP-promoted catalyst-free cascade reactions for the synthesis of biologically relevant 3,3-di(indolyl)indolin-2-ones(27 examples,up to 98% yield) from readily available indoles and isatin derivatives are described.This protocol shows well tolerance of different functional groups and features mild reaction conditions such as short reaction time(~1 h),no usage of catalyst,easy operation and product isolation.Of particular intere st is the formation of two C-C bonds and one all-carbon quaternary center.This protocol could serve as an alternative strategy to synthesize biologically important 3,3-di(indolyl)indolin-2-ones for biological testing.
