Citation: 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]. Chinese Journal of Organic Chemistry, ;2016, 36(9): 2183-2190. doi: 10.6023/cjoc201603023 shu

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

Corresponding author: Wang Shifa, wsfyyq@njfu.com.cn
Received Date: 14 March 2016
Revised Date: 11 April 2016

Fund Project: the Natural National Science Foundation of China 31470529the Open Funding of Jiangsu Key Laboratory of Biomass Energy and Materials JSBEM2014010the University Science Research Project of Jiangsu Province 14KJ220001

Figures(2)

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.
- isolongifolanone,
- 7-arylidene-isolongifolanone,
- pyrazole derivatives,
- anti-inflammatory activity,
- antitumor activity
1. [1]
  Krishnaiah, A.; Narsaiah, B. J. Fluorine Chem. 2002, 115, 9. doi: 10.1016/S0022-1139(01)00501-2
2. [2]
  Du, H. T.; Du, H. J.; Ouyang, G. P. Chin. J. Org. Chem. 2008, 28, 356(in Chinese).
3. [3]
  Tong, J. Y.; Shi, Y. X.; Liu, X. H.; Sun, N. B.; Li, B. J. Chin. J. Org. Chem. 2012, 32, 2373(in Chinese). doi: 10.6023/cjoc201207020
4. [4]
  Nasr, T.; Bondock, S.; Eid, S. Eur. J. Med. Chem. 2014, 84, 492.
5. [5]
  Fadda, A. A.; El-Mekawy, R. E.; El-Shafei, A. I. J. Porphyrins Phthalocyanines 2015, 19, 754.
6. [6]
  Palanisamy, P.; Kumaresan, S. RSC Adv. 2013, 3, 4705.
7. [7]
  Gökhan-Kelekçi, N.; Yabanoğlu, S.; Küpeli, E. Bioorg. Med. Chem. 2007, 15, 5775. doi: 10.1016/j.bmc.2007.06.004
8. [8]
  Lv, P. C.; Li, H. Q.; Sun, J.; Zhou, Y.; Zhu, H. L. Bioorg. Med. Chem. 2010, 18, 4606. doi: 10.1016/j.bmc.2010.05.034
9. [9]
  Goda, F. E.; Maarouf, A. R.; El-Bendary, E. R. Saudi Pharm. J. 2003, 11, 111.
10. [10]
  Rüger, A. J.; Nieger, M.; Bräse, S. Tetrahedron 2012, 68, 8824.
11. [11]
  Dai, H.; Chen, J.; Li, H.; Dai, B. J.; He, H. B.; Fang, Y.; Shi, Y. J. Molecules 2016, 21, 276. doi: 10.3390/molecules21030276
12. [12]
  Foster, R. S.; Jakobi, H.; Harrity, J. P. A. Org. Lett. 2012, 14, 4859.
13. [13]
  Kawamori, T.; Rao, C. V.; Seibert, K.; Reddy, B. S. Cancer Res. 1998, 58, 409.
14. [14]
  Hou, Q. Q.; Li, Z. N.; Liu, C. L. Pesticides 2002, 41, 41(in Chinese).
15. [15]
  Kubota, M.; Yamamoto, K. JP 10130267, 1998[Chem. Abstr. 1998, 129, 41126.]
16. [16]
  Gordien, A. Y.; Gray, A. I.; Franzblau, S. G.; Seidel, V. J. Eth-nopharmacol. 2009, 126, 500.
17. [17]
  Bichlmaier, I.; Kurkela, M.; Siiskonen, A.; Finel, M.; Kauhaluoma, J. Y. Bioorg. Med. Chem. 2007, 35, 386. doi: 10.1016/j.bioorg.2007.07.002
18. [18]
  Zhang, A. J.; Klun, J. A.; Wang, S. F. J. Med. Entomol. 2009, 46, 100. doi: 10.1603/033.046.0113
19. [19]
  Zhang, A.; Carroll, J.; Wang, S.; Klun, J. A. WO 200901209, 2009[Chem. Abstr. 2009, 150, 144686.]
20. [20]
  El-Sayed, M. A.; Abdel-Aziz, N. I.; Abdel-Aziz, A. A.; El-Azab, A. S.; ElTahir, K. E. H. Bioorg. Med. Chem. 2012, 20, 3306. doi: 10.1016/j.bmc.2012.03.044
21. [21]
  Thurmond, R. L.; Beavers, M. P.; Cai, H.; Meduna, S. P.; Gustin, D. J.; Sun, S.; Almond. H. J.; Karlsson, L.; Edwards, J. P. J. Med. Chem. 2004, 47, 4799. doi: 10.1021/jm0496133
22. [22]
  Dinges, J.; Albert, D. H.; Arnold, L. D.; Ashworth, K. L.; Akritopoulou-Zanze, I.; Bousquet, P. F.; Bouska, J. J.; Cunha, G. A.; Davidsen, S. K.; Diaz, G. J.; Djuric, S. W.; Gasiecki, A. F.; Gintant, G. A.; Gracias, V. J.; Harris, C. M.; Houseman, K. A.; Huthins, C. W.; Johnson, E. F.; Li, H.; Marcotte, P. A.; Martin, R. L.; Michaelids, M. R.; Nyein, M.; Sowin, T. J.; Su, Z.; Tapang, P. H.; Xia, Z.; Zhang, H. Q. J. Med. Chem. 2007, 50, 2011. doi: 10.1021/jm061223o
23. [23]
  Klein, O.; Aguilar-Parrilla, F.; Lopez, J. M.; Jagerovic, N.; Elguero, J.; Limbach, H. H. J. Am. Chem. Soc. 2004, 126, 11718. doi: 10.1021/ja0493650
1. [1]
  Jing WU , Puzhen HUI , Huilin ZHENG , Pingchuan YUAN , Chunfei WANG , Hui WANG , Xiaoxia GU . Synthesis, crystal structures, and antitumor activities of transition metal complexes incorporating a naphthol-aldehyde Schiff base ligand. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2422-2428. doi: 10.11862/CJIC.20240278
2. [2]
  Ping Song , Nan Zhang , Jie Wang , Rui Yan , Zhiqiang Wang , Yingxue Jin . Experimental Teaching Design on Synthesis and Antitumor Activity Study of Cu-Pyropheophorbide-a Methyl Ester. University Chemistry, 2024, 39(6): 278-286. doi: 10.3866/PKU.DXHX202310087
3. [3]
  Yurong Tang , Yunren Shi , Yi Xu , Bo Qin , Yanqin Xu , Yunfei Cai . Innovative Experiment and Course Transformation Practice of Visible-Light-Mediated Photocatalytic Synthesis of Isoquinolinone. University Chemistry, 2024, 39(5): 296-306. doi: 10.3866/PKU.DXHX202311087
4. [4]
  Zhongyan Cao , Shengnan Jin , Yuxia Wang , Yiyi Chen , Xianqiang Kong , Yuanqing Xu . Advances in Highly Selective Reactions Involving Phenol Derivatives as Aryl Radical Precursors. University Chemistry, 2025, 40(4): 245-252. doi: 10.12461/PKU.DXHX202405186
5. [5]
  Hong RAO , Yang HU , Yicong MA , Chunxin LÜ , Wei ZHONG , Lihua DU . Synthesis and in vitro anticancer activity of phenanthroline-functionalized nitrogen heterocyclic carbene homo- and heterobimetallic silver/gold complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2429-2437. doi: 10.11862/CJIC.20240275
6. [6]
  Jianfeng Yan , Yating Xiao , Xin Zuo , Caixia Lin , Yaofeng Yuan . Comprehensive Chemistry Experimental Design of Ferrocenylphenyl Derivatives. University Chemistry, 2024, 39(4): 329-337. doi: 10.3866/PKU.DXHX202310005
7. [7]
  Siran Wang , Yinuo Wang , Yilong Zhao , Dazhen Xu . Advances in the Application and Preparation of Rhodanine and Its Derivatives. University Chemistry, 2025, 40(5): 318-327. doi: 10.12461/PKU.DXHX202407033
8. [8]
  Haitang WANG , Yanni LING , Xiaqing MA , Yuxin CHEN , Rui ZHANG , Keyi WANG , Ying ZHANG , Wenmin WANG . Construction, crystal structures, and biological activities of two Ln^Ⅲ₃ complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1474-1482. doi: 10.11862/CJIC.20240188
9. [9]
  Yihui Song , Shangshang Qin , Kai Wu , Chengyun Jin , Bin Yu . 生物化学在高水平创新型药学人才培养中的交叉融合应用——以去甲基化酶LSD1抑制剂的活性评价为例. University Chemistry, 2025, 40(6): 341-352. doi: 10.12461/PKU.DXHX202406018
10. [10]
  Jia-He Li , Yu-Ze Liu , Jia-Hui Ma , Qing-Xiao Tong , Jian-Ji Zhong , Jing-Xin Jian . 洛芬碱衍生物的合成、化学发光与重金属离子检测. University Chemistry, 2025, 40(6): 230-237. doi: 10.12461/PKU.DXHX202407080
11. [11]
  Xin MA , Ya SUN , Na SUN , Qian KANG , Jiajia ZHANG , Ruitao ZHU , Xiaoli GAO . A Tb₂ complex based on polydentate Schiff base: Crystal structure, fluorescence properties, and biological activity. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1347-1356. doi: 10.11862/CJIC.20230357
12. [12]
  Jian Li , Yu Zhang , Rongrong Yan , Kaiyuan Sun , Xiaoqing Liu , Zishang Liang , Yinan Jiao , Hui Bu , Xin Chen , Jinjin Zhao , Jianlin Shi . 高效靶向示踪钙钛矿纳米系统光电增效抗肿瘤. Acta Physico-Chimica Sinica, 2025, 41(5): 100042-. doi: 10.1016/j.actphy.2024.100042
13. [13]
  Jiahao Zeng , Hui Chao . 诱导程序性细胞死亡的金属抗肿瘤药物研究. University Chemistry, 2025, 40(6): 145-159. doi: 10.12461/PKU.DXHX202406019
14. [14]
  Yonghui ZHOU , Rujun HUANG , Dongchao YAO , Aiwei ZHANG , Yuhang SUN , Zhujun CHEN , Baisong ZHU , Youxuan ZHENG . Synthesis and photoelectric properties of fluorescence materials with electron donor-acceptor structures based on quinoxaline and pyridinopyrazine, carbazole, and diphenylamine derivatives. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 701-712. doi: 10.11862/CJIC.20230373
15. [15]
  Yikai Wang , Xiaolin Jiang , Haoming Song , Nan Wei , Yifan Wang , Xinjun Xu , Cuihong Li , Hao Lu , Yahui Liu , Zhishan Bo . 氰基修饰的苝二酰亚胺衍生物作为膜厚不敏感型阴极界面材料用于高效有机太阳能电池. Acta Physico-Chimica Sinica, 2025, 41(3): 2406007-. doi: 10.3866/PKU.WHXB202406007
16. [16]
  Quanliang Chen , Zhaohui Zhou . Research on the Active Site of Nitrogenase over Fifty Years. University Chemistry, 2024, 39(7): 287-293. doi: 10.3866/PKU.DXHX202310133
17. [17]
  Yukai Jiang , Yihan Wang , Yunkai Zhang , Yunping Wei , Ying Ma , Na Du . Characterization and Phase Diagram of Surfactant Lyotropic Liquid Crystal. University Chemistry, 2024, 39(4): 114-118. doi: 10.3866/PKU.DXHX202309033
18. [18]
  Jiayu Gu , Siqi Wang , Jun Ling . Kinetics of Living Copolymerization: A Brief Discussion. University Chemistry, 2025, 40(4): 100-107. doi: 10.12461/PKU.DXHX202406012
19. [19]
  Huijuan Liao , Yulin Xiao , Dong Xue , Mingyu Yang , Jianyang Dong . Synthesis of 1-Benzyl Isoquinoline via the Minisci Reaction. University Chemistry, 2025, 40(7): 294-299. doi: 10.12461/PKU.DXHX202409092
20. [20]
  Ruoxi Sun , Yiqian Xu , Shaoru Rong , Chunmiao Han , Hui Xu . The Enchanting Collision of Light and Time Magic: Exploring the Footprints of Long Afterglow Lifetime. University Chemistry, 2024, 39(5): 90-97. doi: 10.3866/PKU.DXHX202310001

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(844)
HTML views(67)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142