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Letters in Organic Chemistry

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ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

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Research Article

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 and Qian Chen

Volume 16, Issue 12, 2019

Page: [1004 - 1010] Pages: 7

DOI: 10.2174/1570178616666190417115639

Price: $65

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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