Six isochromano [4, 3-c]pyrazole derivatives were synthesized from isochroman-4-one as starting compound. Some of the products show a significant anti-inflammatory activi-ty.
Comprehensive Summary Isochromanone is the core structure of many bioactive compounds.Direct oxidation of isochromans is one of leading methods for the construction of isochromanones,while most established processes r...Comprehensive Summary Isochromanone is the core structure of many bioactive compounds.Direct oxidation of isochromans is one of leading methods for the construction of isochromanones,while most established processes remain suffering from the use of environmentally unfriendly metal oxidants,harsh reaction conditions,and the difficulty in catalyst recycling and product separation.Herein,we report a convenient,cost-effective,and green method for the synthesis of high-value added isochromanones via isochroman oxidations with O_(2) by a novel heterogeneous vanadium cluster catalyst(Cat.1)under mild conditions.This reaction protocol demonstrates high catalytic activity with good catalyst recyclability and reusability for a wide scope of substrates.展开更多
A base-catalyzed ring-opening of 1-benzylisochromans 1 firstly produced 2-alkenylstilbenes 2, which then underwent a mild acid-catalyzed intramolecular cyclization to furnish 1,2-disubstituted indenes 3 in high yields...A base-catalyzed ring-opening of 1-benzylisochromans 1 firstly produced 2-alkenylstilbenes 2, which then underwent a mild acid-catalyzed intramolecular cyclization to furnish 1,2-disubstituted indenes 3 in high yields. Subsequently, a base-catalyzed isomerization of the 1,2-disubstituted indenes 3 afforded the more stable 2,3-disubstituted indenes 4 in almost quantitative yields.展开更多
Two new isochroman derivatives(1 and 2)were isolated from the fermentation products of mangrove endophytic fungus Phomopsis sp.33#.Their structures were characterized by IR,~1 H NMR,H RMS,and single-crystal X-ray crys...Two new isochroman derivatives(1 and 2)were isolated from the fermentation products of mangrove endophytic fungus Phomopsis sp.33#.Their structures were characterized by IR,~1 H NMR,H RMS,and single-crystal X-ray crystallography.The anticancer activity of the two compounds was investigated against four human lung cancer cells(NCI-H292,NCI-H460,LTEP-A-2 and MSTO-211)by 3-(4,5)-dimethylthiahiazo(-z-y1)-3,5-di-phenytetrazoliumromide(MTT)assay.Furthermore,molecular docking studies supported the biological assay data,showing that compared with 1,compound 2 has stronger interaction with protein.展开更多
A new isochroman-4-one, 7,8-dihydroxy-3-methylisochroman-4-one was isolated from water soluble fraction of Musa sapientum L. Its structure was determined by spectroscopic evidences and its total synthesis has also bee...A new isochroman-4-one, 7,8-dihydroxy-3-methylisochroman-4-one was isolated from water soluble fraction of Musa sapientum L. Its structure was determined by spectroscopic evidences and its total synthesis has also been reported. The compound showed potent antihypertensive activity.展开更多
Herein,we report a condition-controlled divergent synthesis of spiro indene-2,1'-isoindolinones and spiro isochroman-3,1'-isoindolinones through cobalt-catalyzed formal[4+1]and[4+1+1]spirocyclization of aromat...Herein,we report a condition-controlled divergent synthesis of spiro indene-2,1'-isoindolinones and spiro isochroman-3,1'-isoindolinones through cobalt-catalyzed formal[4+1]and[4+1+1]spirocyclization of aromatic amides with 2-diazo-1H-indene-1,3(2H)-dione.When the reaction is carried out under air in ethyl acetate,spiro indene-2,1'-isoindolinones are formed through Co(II)-catalyzed C—H/N—H[4+1]spirocyclization.When the reaction is run under O2 in CH3CN,on the other hand,spiro isochroman-3,1'-isoindolinones are generated through Baeyer-Villiger oxidation of the in situ formed spiro indene-2,1'-isoindolinones with O2 as a cheaper and environmental-friendly oxygen source.In general,these protocols have advantages such as using non-precious and earth-abundant metal catalyst,no extra additive,high efficiency and regioselectivity.A gram-scale synthesis and the removal of the directing group further highlight its utility.展开更多
文摘Six isochromano [4, 3-c]pyrazole derivatives were synthesized from isochroman-4-one as starting compound. Some of the products show a significant anti-inflammatory activi-ty.
基金the National Natural Science Foundation of China(22171122)the Liaoning Revitalization Talents Program(XLYC2007130)Talent Scientific Research Fund of Liaoning Petrochemical University(2016XJL-019).
文摘Comprehensive Summary Isochromanone is the core structure of many bioactive compounds.Direct oxidation of isochromans is one of leading methods for the construction of isochromanones,while most established processes remain suffering from the use of environmentally unfriendly metal oxidants,harsh reaction conditions,and the difficulty in catalyst recycling and product separation.Herein,we report a convenient,cost-effective,and green method for the synthesis of high-value added isochromanones via isochroman oxidations with O_(2) by a novel heterogeneous vanadium cluster catalyst(Cat.1)under mild conditions.This reaction protocol demonstrates high catalytic activity with good catalyst recyclability and reusability for a wide scope of substrates.
基金We are grateful to the National Natural Science Foundation of China （No. 20972048） for the financial support of this work
文摘A base-catalyzed ring-opening of 1-benzylisochromans 1 firstly produced 2-alkenylstilbenes 2, which then underwent a mild acid-catalyzed intramolecular cyclization to furnish 1,2-disubstituted indenes 3 in high yields. Subsequently, a base-catalyzed isomerization of the 1,2-disubstituted indenes 3 afforded the more stable 2,3-disubstituted indenes 4 in almost quantitative yields.
基金supported by the Project of Inner Mongolia University for the Nationalities(No.NMDYB15064)Science Research Project of Inner Mongolia Education Department(No.NJZY20114)。
文摘Two new isochroman derivatives(1 and 2)were isolated from the fermentation products of mangrove endophytic fungus Phomopsis sp.33#.Their structures were characterized by IR,~1 H NMR,H RMS,and single-crystal X-ray crystallography.The anticancer activity of the two compounds was investigated against four human lung cancer cells(NCI-H292,NCI-H460,LTEP-A-2 and MSTO-211)by 3-(4,5)-dimethylthiahiazo(-z-y1)-3,5-di-phenytetrazoliumromide(MTT)assay.Furthermore,molecular docking studies supported the biological assay data,showing that compared with 1,compound 2 has stronger interaction with protein.
文摘A new isochroman-4-one, 7,8-dihydroxy-3-methylisochroman-4-one was isolated from water soluble fraction of Musa sapientum L. Its structure was determined by spectroscopic evidences and its total synthesis has also been reported. The compound showed potent antihypertensive activity.
基金the National Natural Science Foundation of China(22101075,U2004189)Central Plains Science and Technology Innovation Leader Project(224200510009)+1 种基金Postdoctoral Research Grant in Henan Province(202103085)Henan Key Laboratory of Organic Functional Molecules and Drug Innovation,and 111 Project(D17007)for financial support.
文摘Herein,we report a condition-controlled divergent synthesis of spiro indene-2,1'-isoindolinones and spiro isochroman-3,1'-isoindolinones through cobalt-catalyzed formal[4+1]and[4+1+1]spirocyclization of aromatic amides with 2-diazo-1H-indene-1,3(2H)-dione.When the reaction is carried out under air in ethyl acetate,spiro indene-2,1'-isoindolinones are formed through Co(II)-catalyzed C—H/N—H[4+1]spirocyclization.When the reaction is run under O2 in CH3CN,on the other hand,spiro isochroman-3,1'-isoindolinones are generated through Baeyer-Villiger oxidation of the in situ formed spiro indene-2,1'-isoindolinones with O2 as a cheaper and environmental-friendly oxygen source.In general,these protocols have advantages such as using non-precious and earth-abundant metal catalyst,no extra additive,high efficiency and regioselectivity.A gram-scale synthesis and the removal of the directing group further highlight its utility.
