Citation: Hui Hong, Long Jiang Huang, Da Wei Teng. A spirocyclic oxindole analogue:Synthesis and antitumor activities[J]. Chinese Chemical Letters, ;2011, 22(9): 1009-1012. doi: 10.1016/j.cclet.2011.01.042 shu

A spirocyclic oxindole analogue:Synthesis and antitumor activities

College of Chemical Engineering, Qingdao University of Science & Technology, Qingdao 266042, China

Received Date: 6 December 2010

Fund Project: This research was financially supported by the program of research fund for returning scholars of Ministry of Education of China (No.200812) and the Open Foundation of Chemical Engineering Subject (No.200903), Qingdao University of Science&Technology, China.

A new synthesis of spirocyclic oxindole analogue spirofpiperidine-4, 3'-pyrrolo[2, 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).
- Spirocyclic oxindole,
- Aryl amidation,
- Dialkylation,
- Antitumor activity
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