Synthesis, Antitumor and Anti-inflammatory Activities of Isolongifolanonyl Pyrazole Derivatives

doi:10.6023/cjoc201603023

Chin. J. Org. Chem. ›› 2016, Vol. 36 ›› Issue (9): 2183-2190.DOI: 10.6023/cjoc201603023 Previous Articles Next Articles

ARTICLE

异长叶烷基吡唑类衍生物的合成及其抗肿瘤、抗炎活性研究

芮坚^a, 杨金来^a, 黄建峰^a, 王佳瑜^a, 徐徐^a,b,c, 徐海军^a, 王石发^a,b,c

a 南京林业大学化学工程学院南京 210037;
b 江苏省生物质能源与材料重点实验室南京 210042;
c 广西林产化学与工程重点实验室南宁 530008

收稿日期:2016-03-14 修回日期:2016-04-11 发布日期:2016-05-06
通讯作者: 王石发 E-mail:wsfyyq@njfu.com.cn
基金资助:
江苏省高校自然科学研究重大项目（No.14KJ220001）、国家自然科学基金（No.31470529）和江苏省生物质能源与材料重点实验室开放基金（No.JSBEM2014010）资助项目.

Synthesis, Antitumor and Anti-inflammatory Activities of Isolongifolanonyl Pyrazole Derivatives

Rui Jian^a, Yang Jianlai^a, Huang Jianfeng^a, Wang Jiayu^a, Xu Xua^a,b,c, Xu Haijun^a, Wang Shifa^a,b,c

a College of Chemical Engineering, Nanjing Forestry University, Nanjing 210037;
b Key Laboratory of Biomass Energy and Material of Jiangsu Province, Nanjing 210042;
c Guangxi Key Laboratory of Chemistry and Engineering of Forest Products, Nanning 530008

Received:2016-03-14 Revised:2016-04-11 Published:2016-05-06
Supported by:
Project supported by the University Science Research Project of Jiangsu Province (No.14KJ220001), the Natural National Science Foundation of China (No.31470529), and the Open Funding of Jiangsu Key Laboratory of Biomass Energy and Materials (No.JSBEM2014010).

1. Synthesis, Antitumor and Anti-inflammatory Activities of Isolongifolanonyl Pyrazole Derivatives.PDF(1578KB)

Abstract

A series of new isolongifolanonyl pyrazole derivatives 3a~3j were synthesized by aldol-condensation, cyclization and dehydroaromatization from isolongifolanone. The yields of products ranged from 69.5% to 76.5%. The chemical structures of compounds obtained were elucidated by ¹H NMR, ¹³C NMR, IR, MS spectra and elemental analysis. The strucure of compound 3i was determined by X-ray single crystal diffraction. Their inhibitory activities against human hepatoma cell (HepG2) and human umbilical vein endothelial cell (HUVECs) were evaluated. The results indicated that compounds 3h and 3i[IC₅₀=(15.42±0.6), (4.74±0.3) μmol/L] showed obvious inhibitory activity against HUVECs. Compounds 3a, 3c,3e and 3j[IC₅₀=(5.27±0.5), (6.71±0.4), (4.68±0.2), (4.57±0.5)] μmol/L showed better antitumor activity against HepG₂.

Key words: isolongifolanone, 7-arylidene-isolongifolanone, pyrazole derivatives, anti-inflammatory activity, antitumor activity

Cite this article

Rui Jian, Yang Jianlai, Huang Jianfeng, Wang Jiayu, Xu Xua, Xu Haijun, Wang Shifa. Synthesis, Antitumor and Anti-inflammatory Activities of Isolongifolanonyl Pyrazole Derivatives[J]. Chin. J. Org. Chem., 2016, 36(9): 2183-2190.

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异长叶烷基吡唑类衍生物的合成及其抗肿瘤、抗炎活性研究

Synthesis, Antitumor and Anti-inflammatory Activities of Isolongifolanonyl Pyrazole Derivatives

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