A concise and efficient method for the synthesis of novel 9,10-imethoxybenzo[6,7]oxepino[3,4-b]quinolin13(6H)-one and its derivatives 7a-p has been developed via the intramolecular Friedel-Crafts acylation reactions o...A concise and efficient method for the synthesis of novel 9,10-imethoxybenzo[6,7]oxepino[3,4-b]quinolin13(6H)-one and its derivatives 7a-p has been developed via the intramolecular Friedel-Crafts acylation reactions of 6,7-dimethoxy-2-(phenoxymethyl)quinoline-3-carboxylic acids 6a-p with polyphosphoric acid (PPA) as catalyst and solvent under mild conditions. The key intermediates 6a-p were prepared through the in situ formation of ethyl 6,7-dimethoxy-2-(phenoxymethyl)quinoline-3-carboxylates 5a-p followed by hydrolysis with aqueous ethanolic sodium hydroxide solution. The novel synthetic method has the advantages of good yields, easy work-up, and environmentally friendly character, which may provide a novel highly efficient process for making quinoline and related azaheterocycle libraries.展开更多
Bromination is used as a strategy to improve biological activity in medicinal chemistry.In order to study on the structure-activity relationships of the novel acetylcholinesterase inhibitors with 7H-thiazolo[3,2-b]-1,...Bromination is used as a strategy to improve biological activity in medicinal chemistry.In order to study on the structure-activity relationships of the novel acetylcholinesterase inhibitors with 7H-thiazolo[3,2-b]-1,2,4-triazin-7-one scaffold,based on our previous work and molecular modeling,a series of novel 3-aryl-6-（bromoarylrnethyl）-7H-thiazolo[3,2-b]-1,2,4-triazin-7-one derivatives were designed by molecular docking,synthesized and characterized by mass spectra,infrared spectra,proton NMR and elemental analyses.The study of AChE inhibitory activity was carried out using the Ellman colorimetric assay with huperzine-A as the positive control.Most of all target compounds exhibited more than 45%inhibition at 10μmol/L.The preliminary structureactivity relationship was the bromine atoms and the hydroxyl group at the phenyl ring at the C6 position of the parent nucleus played significant roles in the AChE inhibitory activity of the target compounds.展开更多
Two novel Jr-conjugated cyanostilbene derivatives, FLU-CNPH and TPE-CNPH, were designed aria synthesized by introducing the strong electron donor 1, 4-dihydropyrro[3,2-b]indole and AIE electron donor tetraphenylethyle...Two novel Jr-conjugated cyanostilbene derivatives, FLU-CNPH and TPE-CNPH, were designed aria synthesized by introducing the strong electron donor 1, 4-dihydropyrro[3,2-b]indole and AIE electron donor tetraphenylethylene （TPE） to the （3＇,5＇-bis（trifluoromethyl）-biphenyl-4-yl）-acetonitrile, respec- tively, Both of them were fully characterized and their AIE behaviors were investigated using fluorescence spectroscopy and FE-SEM images. Their optimized structures and frontier molecular orbitals were calculated with the DFT by using Materials Studio 7,0 software to study the relationship between the structure and properties.展开更多
文摘A concise and efficient method for the synthesis of novel 9,10-imethoxybenzo[6,7]oxepino[3,4-b]quinolin13(6H)-one and its derivatives 7a-p has been developed via the intramolecular Friedel-Crafts acylation reactions of 6,7-dimethoxy-2-(phenoxymethyl)quinoline-3-carboxylic acids 6a-p with polyphosphoric acid (PPA) as catalyst and solvent under mild conditions. The key intermediates 6a-p were prepared through the in situ formation of ethyl 6,7-dimethoxy-2-(phenoxymethyl)quinoline-3-carboxylates 5a-p followed by hydrolysis with aqueous ethanolic sodium hydroxide solution. The novel synthetic method has the advantages of good yields, easy work-up, and environmentally friendly character, which may provide a novel highly efficient process for making quinoline and related azaheterocycle libraries.
基金supported by the National Natural Science Foundation ofChina(No.21072130)
文摘Bromination is used as a strategy to improve biological activity in medicinal chemistry.In order to study on the structure-activity relationships of the novel acetylcholinesterase inhibitors with 7H-thiazolo[3,2-b]-1,2,4-triazin-7-one scaffold,based on our previous work and molecular modeling,a series of novel 3-aryl-6-（bromoarylrnethyl）-7H-thiazolo[3,2-b]-1,2,4-triazin-7-one derivatives were designed by molecular docking,synthesized and characterized by mass spectra,infrared spectra,proton NMR and elemental analyses.The study of AChE inhibitory activity was carried out using the Ellman colorimetric assay with huperzine-A as the positive control.Most of all target compounds exhibited more than 45%inhibition at 10μmol/L.The preliminary structureactivity relationship was the bromine atoms and the hydroxyl group at the phenyl ring at the C6 position of the parent nucleus played significant roles in the AChE inhibitory activity of the target compounds.
基金financially supported by NSFC(Nos.21372194,21476075 and 21272072)the Guangdong Yangfan Talent Plan(2013)the Research Funds of Lingnan Normal University(No.QL1402)
文摘Two novel Jr-conjugated cyanostilbene derivatives, FLU-CNPH and TPE-CNPH, were designed aria synthesized by introducing the strong electron donor 1, 4-dihydropyrro[3,2-b]indole and AIE electron donor tetraphenylethylene （TPE） to the （3＇,5＇-bis（trifluoromethyl）-biphenyl-4-yl）-acetonitrile, respec- tively, Both of them were fully characterized and their AIE behaviors were investigated using fluorescence spectroscopy and FE-SEM images. Their optimized structures and frontier molecular orbitals were calculated with the DFT by using Materials Studio 7,0 software to study the relationship between the structure and properties.
