A spirocyclic oxindole analogue： Synthesis and antitumor activities

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 chlori...

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Bibliographic Details
Published in:Chinese chemical letters 2011-09, Vol.22 (9), p.1009-1012
Main Authors: Hong, Hui, Huang, Long Jiang, Teng, Da Wei
Format: Article
Language:English
Subjects:
Antitumor activity
Aryl amidation
Dialkylation
IC50
Spirocyclic oxindole
人肝癌细胞
合成
小型图书馆
抗肿瘤活性
模拟
肺癌细胞
螺环
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Summary: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）.
ISSN:1001-8417
1878-5964
DOI:10.1016/j.cclet.2011.01.042