Citation: Li Yongkun, Liu Bei, Zhang Lijun, Zhu Jiahong, Wan Chunping, Mao Zewei. Synthesis and Cytotoxic Activity of New 3-Aryl-5-furanyl-4, 5-dihydroisoxazoline Derivatives[J]. Chinese Journal of Organic Chemistry, ;2018, 38(4): 949-954. doi: 10.6023/cjoc201711005 shu

Synthesis and Cytotoxic Activity of New 3-Aryl-5-furanyl-4, 5-dihydroisoxazoline Derivatives

Li Yongkun ^a,† ,
Liu Bei ^a,† ,
Zhang Lijun ^a ,
Zhu Jiahong ^a ,
Wan Chunping ^b,, ,
Mao Zewei ^a,,

a.
College of Pharmaceutical Science, Yunnan University of Traditional Chinese Medicine, Kunming 650500
b.
Central Laboratory, The No.1 Affiliated Hospital of Yunnan University of Traditional Chinese Medicine, Kunming 650021

Corresponding author: Wan Chunping, wanchunping1012@163.com Mao Zewei, maozw@ynutcm.edu.cn
Received Date: 2 November 2017
Revised Date: 4 December 2017
Available Online: 15 April 2017
Fund Project: Project supported by the National Natural Science Foundation of China (No. 81460624) and the Yunnan Provincial Science and Technology Department-Applied Basic Research Joint Special Funds of Yunnan University of Traditional Chinese Medicine (No. 2017FF117 (-023))the National Natural Science Foundation of China 81460624the Yunnan Provincial Science and Technology Department-Applied Basic Research Joint Special Funds of Yunnan University of Traditional Chinese Medicine 2017FF117 (-023)

Figures(4)

Dihydroisoxazoline is a heterocyclic compound with a variety of biological properties. In this study, ten new 3-(4-piperazinyl)phenyl-5-(2-furyl)-4, 5-dihydroisoxazoline derivatives (3~12) have been prepared by the general principle of molecular hybridization based on former work. The structures were characterized by IR, ¹H NMR, ¹³C NMR and HRMS. In vitro cytotoxic activity against a panel of human tumor cell lines (Hela, A549 and SGC7901) was evaluated by the 3-(4, 5-dimethyl-2-thiazolyl)-2, 5-diphenyl-2H-tetrazolium bromide (MTT) assay. The result indicated that dihydroisoxazoline derivatives showed potential cytotoxic activity, and the substituents of the NH group of piperazine ring had an obvious influence on cytotoxic activities. Especially, compound 4, 6 and 11 were found to be better inhibition against human tumor cell lines, which were found to be similar cytotoxic activity to positive control 5-fluorouracil. Further FACs analysis showed that compounds 4 and 11 significantly induced death in A549 cell.
- dihydroisoxazoline,
- synthesis,
- cytotoxic activity,
- FACs analysis
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