Citation: Mao Zewei, Liu Bei, Zhu Ping, Zhang Lijun, Zhu Jiahong, Wu Linze, Wan Chunping. Synthesis and Biological Evaluation of Piperazine Substituted 3-Aryl-5-furanyldihydropyrazole Amide Derivatives[J]. Chinese Journal of Organic Chemistry, ;2018, 38(8): 2167-2173. doi: 10.6023/cjoc201802010 shu

Synthesis and Biological Evaluation of Piperazine Substituted 3-Aryl-5-furanyldihydropyrazole Amide Derivatives

Mao Zewei ^a,†,, ,
Liu Bei ^a,† ,
Zhu Ping ^a ,
Zhang Lijun ^a ,
Zhu Jiahong ^a ,
Wu Linze ^a ,
Wan Chunping ^b,,

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: Mao Zewei, maozw@ynutcm.edu.cn Wan Chunping, wanchunping1012@163.com
Received Date: 6 February 2018
Revised Date: 27 March 2018
Available Online: 27 August 2018
Fund Project: the Yunnan Provincial Science and Technology Department-Applied Basic Research Joint Special Funds of Yunnan University of Traditional Chinese Medicine 2017FF117(-023)the National Natural Science Foundation of China 81460624Project 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))

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Pyrazole is a five-membered heterocyclic molecule with a broad range of biological activities. In this study, a series of new 3-aryl-5-furanyl-4, 5-dihydropyrazole derivatives have been designed and synthesized by the general principle of molecular hybridization. The structures were characterized by ¹H NMR, ¹³C NMR and HRMS. We screened in vitro anti-inflammatory in lipopolysaccharide (LPS)-stimulated RAW-264.7 macrophages and anticancer activity against 3 strains human tumor cell lines (A549, Hela and SGC7901) by the methyl thiazolyl tetrazolium (MTT) assay. The result indicated that dihydropyrazole compounds showed good inhibitory effect on the generation of NO and selective cytotoxic activity against tumor cell lines, and the acyl moieties of amides had an obvious influence on biological activities. Especially, 3 compounds were found to be similar anti-inflammatory to positive control dexamethasone, and 3 compounds displayed similar selective anti-tumor activity to positive control 5-fluorouracil (5-FU), which were to be lead compounds for further SAR research.
- dihydropyrazole,
- amide,
- anti-inflammatory activity,
- anticancer activity
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