Chinese Journal of Organic Chemistry >
Synthesis and Biological Activities of 3-Methoxy-6-substituted-5,6-dihydropyrrolo[3,4-b]pyridin-7-ones
Received date: 2013-09-24
Revised date: 2013-10-14
Online published: 2013-11-20
Supported by
Project supported by the National Significant and Special Project of New Created Drugs (No. 2010ZX09401-404).
A series of thalidomide derivatives named 3-methoxy-6-substituted 5,6-dihydropyrrolo[3,4-b]pyridin-7-ones 1a～1l, which have never been reported in literature, were synthesized from 3-methyl pyridine-2-carboxylic acid methyl ester (7) and different amines by cyclization reaction. The intermediate 7 was produced via hydrolysis, esterification, nitration reaction, methoxy substitution, bromination reaction using 3-methyl-pyridine-2-carbonitrile as the starting material. The structures of all compounds have been confirmed by 1H NMR, 13C NMR and HRMS techniques. The target compounds were evaluated for their inhibitory activity against HCT-116, MG-63, MCF-7, HUVEC and HMVEC cells by MTT (thiazolyl blue tetrazolium bromide) method, and the results indicated that almost all of them had no obvious inhibitory effect on normal human cells, compounds 1h～1l only displayed obvious inhibitory effect on MG-63 cells while compounds 1c～1g presented excellent inhibitory activities against all the three kinds of tumor cells, among which compounds 1d and 1e exhibited most potent activities.
Sun Guanglong , Zhang Weiwei , Zhan Xiaoping , Liu Zenglu , Mao Zhenmin . Synthesis and Biological Activities of 3-Methoxy-6-substituted-5,6-dihydropyrrolo[3,4-b]pyridin-7-ones[J]. Chinese Journal of Organic Chemistry, 2014 , 34(3) : 546 -551 . DOI: 10.6023/cjoc201309033
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