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Letters in Organic Chemistry

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

DOI: 10.2174/1570178616666190417115639

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Synthesis and Biological Evaluation of Isofebrifugine Analogues

Page: [1004 - 1010] Pages: 7

  • * (Excluding Mailing and Handling)

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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