Synthesis and Biological Evaluation of Isofebrifugine Analogues

Author(s): Jinjin Zhang, Baohua Huang*, Yujing Lu, Wenbin Li, Zichong Zhuang, Donghua Ke, Jingpeng Zhong, Jinlin Zhou, Qian Chen

Journal Name: Letters in Organic Chemistry

Volume 16 , Issue 12 , 2019


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Abstract:

Isofebrifugine, as a kind of natural quinazolinone alkaloid with important physiological activities and good pharmacological effects, was isolated from a Chinese medicinal plant, Chang Shan (Dichroa febrifuga). In this paper, the synthesis of a series of novel isofebrifugine analogues was accomplished by employing the N-alkylation of 4(3H)-quinazolinones with benzyl (3aR,7aR)-rel-2- (bromomethyl)hexahydrofuro[3,2-b]pyridine-4(2H)carboxylates and the subsequent N-deprotection. These analogues were characterized by 1H NMR, 13C NMR and HRMS spectra. The MTT assay was used to examine the inhibitory effects of these analogues on the growth of human hepatoma cells (HepG2). The results indicated that some halogenated or hemiketal analogues showed interesting inhibition activity.

Keywords: Isofebrifugine, analogue, piperidine, quinazolinone, convergent synthesis, HepG2.

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Article Details

VOLUME: 16
ISSUE: 12
Year: 2019
Published on: 08 October, 2019
Page: [1004 - 1010]
Pages: 7
DOI: 10.2174/1570178616666190417115639
Price: $65

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