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A spirocyclic oxindole analogue:Synthesis and antitumor activities

Chinese Chemical Letters 2011年第9期22卷 1009-1012页

作者： Hui Hong Long Jiang Huang Da Wei Teng College of Chemical Engineering Qingdao University of Science & Technology Qingdao 266042 China

A new synthesis of spirocyclic oxindole analogue spiro[piperidine-4,3＇-pyrrolol2,3-b]pyridin]-2＇（1＇H）-one 1 is described. The key steps involve dialkylation of arylacetonitrile and cyclization of the azaoxindole ring by an intramolecular Buchwald-Hartwig amidation of carboxylic amide and aryl chloride. A small library was obtained by reductive amination of 1 with various aldehydes and was screened against human lung cancer cell A549, human liver cancer cell BEL7402, and human colon cancer cell HCT-8. The results show that most of the library compounds 2 have some inhibitory activities. 2-（Trifluoromethoxy） benzylic substituted spirocyclic azaoxindole 2e was identified as a nanomolar inhibitor against human lung cancer cell A-549 （IC50 = 50 nmol/L）.

关键词： spirocyclic oxindole Aryl amidation Dialkylation Antitumor activity

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Asymmetric Double Michael Reaction Catalyzed by Simple Primary Amine Catalysts： A Straightforward Approach to Construct spirocyclic oxindoles

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Chinese Journal of Chemistry 2012年第5期30卷 1185-1188页

作者：罗西娅汪亮亮彭林摆建飞贾利娜贺光云田芳徐小英王立新 Key Laboratory of Asymmetric Synthesis and Chirotechnology of Sichuan Province Chengdu Institute of Organic ChemistryChinese Academy of SciencesChengduSichuan 610041China Graduate University of Chinese Academy of Sciences Beijing 10039China

The enantioselective double Michael reaction of N-Boc-3-nonsubstitued oxindoles with dienones catalyzed by chiral monoimide protected cyclohexane-1,2-diamines was developed. A wide range of optically active spirocycli... 详细信息

关键词： double Michael reaction spirocyclic oxindole amine catalyst organocatalysis

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N-Heterocyclic Carbene-Catalyzed[4+2]Cyclization of α-bromo-enal with 3-alkylenyloxindoles:an efficient synthesis of spirocyclic oxindoles

N-Heterocyclic Carbene-Catalyzed[4+2]Cyclization of α-bromo...

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中国化学会全国第十一届有机合成化学学术研讨会

作者： Yuanwei Xie Zhaoxin Xiao Tuanjie Li Rui Liu Chenxia Yu Changsheng Yao School of Chemistry and Chemical Engineering Jiangsu Normal University

N-heterocyclic carbene(NHC) catalyzed reactions have emerged as an particularly fruitful area of research in organic chemistry. Due to the unique "Umpolung" in organic synthesis,umpoluping the aldehydes to acyl nucleophiles has become an important way to synthesis of heterocyclic compounds in current research. Spirooxindole cores are interesting and important structures found in many bioactive natural products,and the functionalized six-membered spirooxindole core structure is featured in many natural products as well as medicinally relevant compounds. Herein we shall report our preliminary results of an NHC-catalyzed reaction of 2-bromo-2-enal bearing γ-H with 3-alkylenyloxindoles,which may give the desired spirocarbocyclic oxindoles with potential bioactivity.

关键词： NHC spirocyclic oxindole α-bromo-enal 3-alkylenyloxindole

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