Citation: Liu Juanjuan, Lu Yanju, Wang Jing, Bi Liangwu, Zhao Zhendong. Synthesis and Bioactivity Evaluation of Acylthiourea Derivatives Based on Isopimaric Acid[J]. Chinese Journal of Organic Chemistry, ;2017, 37(3): 731-738. doi: 10.6023/cjoc201610017 shu

Synthesis and Bioactivity Evaluation of Acylthiourea Derivatives Based on Isopimaric Acid

Liu Juanjuan ^a ,
Lu Yanju ^a,b ,
Wang Jing ^a,b ,
Bi Liangwu ^a,b ,
Zhao Zhendong ^a,b,*,,

a.
Institute of Chemical Industry of Forest Product, Chinese Academy of Forestry, National Engineering Laboratory for Biomass Chemical Utilization, Key and Open Laboratory on Forest Chemical Engineering State Forestry Adminstration, Key Laboratory of Biomass Energy and Material, Nanjing 210042
b.
Research Institute of Forestry New Technology, Chinese Academy of Forestry, Beijing 100091

Corresponding author: Zhao Zhendong, zdzhao@189.cn
Received Date: 12 October 2016
Revised Date: 7 December 2016

Fund Project: the National Natural Science Foundation of China 31370575

Figures(2)

To develop isopimaric acid derivatives with high bioactivity, fifteen acyl (amide) thiourea derivatives containing isopimaric acid skeleton were synthesized and confirmed by FT-IR, ¹H NMR, ¹³C NMR and HRMS or elemental analysis. All the compounds were evaluated for their antibacterial and anticancer activity. Most of the compounds showed siginificant inhibitory activity which was higher than that of isopiamric acid against the Candida Albicans. At the concentration of 100 μmol/L, many compounds exhibited pronounced inhibitory effects on human melanoma cells (A375) and prostatic carcinoma (PC-3) cell lines, especially compounds N-isopimaric acyl-N'-(3-methylphenyl) sulfourea (3c) and N-isopimaric acylamino-N'-(4-fluorophenyl) sulfourea (6b) have the best anticancer activity, both with the inhibitory rate of over 90%.
- isopimaric acid,
- acylthiourea,
- antibacterial activity,
- anticancer activity,
- structure-activity relationship
1. [1]
  Rabergh, C. M. I.; Lilius, H.; Eriksson, J. E.; Isomaa, B. Aquat. Toxicol. 1999, 46, 55. doi: 10.1016/S0166-445X(98)00115-5
2. [2]
  Nikinmaa, M.; Wickström, C.; Lilius, H.; Isomaa, B.; Rabergh, C. Environ. Toxicol. Chem. 1999, 18, 993. doi: 10.1002/etc.v18:5
3. [3]
  Henney, N. C.; Li, B.; Elford, C.; Campbell, A. Am. J. Physiol. Cell Physiol. 2009, 297, C1397. doi: 10.1152/ajpcell.00311.2009
4. [4]
  Wu, C.; Gopal, K. V.; Lukas, T. J.; Gross, G. W.; Moore, E. J. Eur. J. Pharmacology 2014, 732, 68. doi: 10.1016/j.ejphar.2014.03.017
5. [5]
  Wang, L.; Kang, H.-C.; Li, Y.-Z.; Shui, Y.; Yamamoto, R.; Sugai, T.; Kato, N. Neuropharmacol. 2015, 92, 8. doi: 10.1016/j.neuropharm.2014.12.033
6. [6]
  Sharma, S.; Nagar, V.; Mehta, B. K. Fitoterapia 1993, 64, 476.
7. [7]
  Tanaka, R.; Tokuda, H.; Ezaki, Y. Phytomedicine 2008, 15, 985. doi: 10.1016/j.phymed.2008.02.020
8. [8]
  Chang, L. C.; Song, L. L.; Park, E. J.; Luyengi, L.; Lee, K. J.; Farnsworth, N. R.; Pezzuto, J. M.; Kinqhorn, A. D. J. Nat. Prod. 2000, 63, 1235. doi: 10.1021/np0001575
9. [9]
  Adamczyk, S.; Adamczyk, B.; Kitunen, V.; Smolander, A. Soil Biol. Biochem. 2015, 87, 59. doi: 10.1016/j.soilbio.2015.04.006
10. [10]
  Bisio, A.; Fraternale, D.; Damonte, G.; Millo, E.; Lanteri, A. P.; Russo, E.; Romussi, G.; Parodi, B.; Ricci, D.; De Tommasi, N. Nat. Prod. Commun. 2009, 4, 1621.
11. [11]
  Elliger, C. A.; Zinkel, D. F.; Chan, B. G.; Waiss, A. C., Jr. Experientia 1976, 32, 1364. doi: 10.1007/BF01937376
12. [12]
  Perez Gutierrez, R. M.; Garcia, B. E. J. Asian Nat. Prod. Res. 2011, 13, 934. doi: 10.1080/10286020.2011.601744
13. [13]
  Cheng, S.-S.; Chang, S.-T. Wood Sci. Technol. 2014, 48, 831. doi: 10.1007/s00226-014-0644-1
14. [14]
  Xie, Y. S.; Isman, M. B.; Yi, F.; Wong, A. J. Chem. Ecol. 1993, 19, 1075. doi: 10.1007/BF00987370
15. [15]
  Gong, Y.-X.; Wang, Z.-Y.; Zhang, Z.-W.; Chen, C.-B.; Wang, Y.-G. Chin. J. Org. Chem. 2006, 26, 360 (in Chinese).
16. [16]
  Zou, X.-J.; Jin, G.-Y.; Yang, Z. Chem. J. Chin. Univ. 2002, 23, 403 (in Chinese).
17. [17]
  Su, G.-F.; Huo, L.-N.; Qin, J.-K.; Pan, C.-X.; Guan, Y.-F. Chin. J. Appl. Chem. 2008, 25, 803 (in Chinese).
18. [18]
  Elkholy, S. S.; Salem, H. A.; Eweis, M.; Elsabee, M. Z. Int. J. Biol. Macromol. 2014, 70, 199. doi: 10.1016/j.ijbiomac.2014.05.068
19. [19]
  Plutín, A. M.; Mocelo, R.; Alvarez, A.; Ramos, R.; Castellano, E. E.; Cominetti, M. R.; Graminha, A. E.; Ferreira, A. G.; Batista, A. A. J. Inorg. Biochem. 2014, 134, 76. doi: 10.1016/j.jinorgbio.2014.01.022
20. [20]
  Koca, İ.; Özgür, A.; Coşkun, K. A.; Tutar, Y. Bioorg. Med. Chem. 2013, 21, 3859. doi: 10.1016/j.bmc.2013.04.021
21. [21]
  Wang, Y.-G.; Lu, B.-X.; Ye, W.-F.; Zhao, X.-Y.; Yang, J. Chin. J. Org. Chem. 2002, 22, 862 (in Chinese).
22. [22]
  Su, G.-F.; Huo, L.-N.; Chen, R.; Zhao, F.-L.; Guan, Y.-F. Acta Chim. Sinica 2008, 66, 2717 (in Chinese).
23. [23]
  Ulubelen, A.; Oksüz, S.; Topcu, G.; Gören, A. C.; Bozok-Johansson, C.; Celik, C.; Kökdil, G.; Voelter, W. Nat. Pro. Lett. 2001, 15, 307. doi: 10.1080/10575630108041297
24. [24]
  Zhao, Z.-D.; Li, X.-D.; Bi, L.-W.; Chen, Y.-X.; Gu, Y.; Li, D.-M.; Wang, J. J. CN 101302151, 2008[Chem. Abstr. 2008, 150, 5919].
25. [25]
  Hilliard, N. J.; Duffy, L. B.; Crabb, D. M.; Waites, K. B. J. Microbiol. Methods 2005, 60, 285. doi: 10.1016/j.mimet.2004.10.007
26. [26]
  Liu, Z.-J.; Wu, S.-S.; Wang, Y.; Li, R.-J.; Wang, J.; Wang, L.-H.; Zhao, Y.-F.; Gong, P. Eur. J. Med. Chem. 2014, 87, 782. doi: 10.1016/j.ejmech.2014.10.022
1. [1]
  Xinting XIONG , Zhiqiang XIONG , Panlei XIAO , Xuliang NIE , Xiuying SONG , Xiuguang YI . Synthesis, crystal structures, Hirshfeld surface analysis, and antifungal activity of two complexes Na(Ⅰ)/Cd(Ⅱ) assembled by 5-bromo-2-hydroxybenzoic acid ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1661-1670. doi: 10.11862/CJIC.20240145
2. [2]
  Xuejie Wang , Guoqing Cui , Congkai Wang , Yang Yang , Guiyuan Jiang , Chunming Xu . Research Progress on Carbon-based Catalysts for Catalytic Dehydrogenation of Liquid Organic Hydrogen Carriers. Acta Physico-Chimica Sinica, 2025, 41(5): 100044-0. doi: 10.1016/j.actphy.2024.100044
3. [3]
  Ruizhi Duan , Xiaomei Wang , Panwang Zhou , Yang Liu , Can Li . The role of hydroxyl species in the alkaline hydrogen evolution reaction over transition metal surfaces. Acta Physico-Chimica Sinica, 2025, 41(9): 100111-0. doi: 10.1016/j.actphy.2025.100111
4. [4]
  Lei Feng , Ze-Min Zhu , Ying Yang , Zongbin He , Jiafeng Zou , Man-Bo Li , Yan Zhao , Zhikun Wu . Long-Pursued Structure of Au₂₃(S-Adm)₁₆ and the Unexpected Doping Effects. Acta Physico-Chimica Sinica, 2024, 40(5): 2305029-0. doi: 10.3866/PKU.WHXB202305029
5. [5]
  Haiying Jiang , Liuhong Song , Yangyang Cheng , Kefen Yue , Mingli Peng , Huilin Guo . Ph―C≡C―Cu_2.5的力致变色现象探究——推荐一个物理化学实验. University Chemistry, 2025, 40(8): 249-254. doi: 10.12461/PKU.DXHX202410003
6. [6]
  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
7. [7]
  Lifang HE , Wenjie TANG , Yaoze LUO , Mingsheng LIANG , Jianxin TANG , Yuxuan WU , Fuxing ZHANG , Xiaoming ZHU . Synthesis, structure, and anticancer activity of two dialkyltin complexes constructed based on 2, 2′-bipyridin-6, 6′-dicarboxylic acid. Chinese Journal of Inorganic Chemistry, 2025, 41(8): 1601-1609. doi: 10.11862/CJIC.20250012
8. [8]
  Xue-Peng Zhang , Yuchi Long , Yushu Pan , Jiding Wang , Baoyu Bai , Rui Ding . 定量构效关系方法学习探索：以钴卟啉活化氧气为例. University Chemistry, 2025, 40(8): 345-359. doi: 10.12461/PKU.DXHX202410107
9. [9]
  Jingjing QING , Fan HE , Zhihui LIU , Shuaipeng HOU , Ya LIU , Yifan JIANG , Mengting TAN , Lifang HE , Fuxing ZHANG , Xiaoming ZHU . Synthesis, structure, and anticancer activity of two complexes of dimethylglyoxime organotin. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1301-1308. doi: 10.11862/CJIC.20240003
10. [10]
  Yao HUANG , Yingshu WU , Zhichun BAO , Yue HUANG , Shangfeng TANG , Ruixue LIU , Yancheng LIU , Hong LIANG . Copper complexes of anthrahydrazone bearing pyridyl side chain: Synthesis, crystal structure, anticancer activity, and DNA binding. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 213-224. doi: 10.11862/CJIC.20240359
11. [11]
  Jia JI , Zhaoyang GUO , Wenni LEI , Jiawei ZHENG , Haorong QIN , Jiahong YAN , Yinling HOU , Xiaoyan XIN , Wenmin WANG . Two dinuclear Gd(Ⅲ)-based complexes constructed by a multidentate diacylhydrazone ligand: Crystal structure, magnetocaloric effect, and biological activity. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 761-772. doi: 10.11862/CJIC.20240344
12. [12]
  Peipei CUI , Yawen ZHENG , Pan LI , Peiyan GUAN , Zhaohong QIAN . Praseodymium-organic framework with 4, 4′-oxybis(benzoic acid): Rare broken layer structure, antibacterial activity, and sensing for Cd²⁺ ions. Chinese Journal of Inorganic Chemistry, 2025, 41(8): 1641-1649. doi: 10.11862/CJIC.20250152
13. [13]
  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
14. [14]
  Guanghui SUI , Yanyan CHENG . Application of rice husk-based activated carbon-loaded MgO composite for symmetric supercapacitors. Chinese Journal of Inorganic Chemistry, 2025, 41(3): 521-530. doi: 10.11862/CJIC.20240221
15. [15]
  Xiaotong LU , Pan ZHANG , Zijie ZHAO , Lei HUANG , Hongwei ZUO , Lili LIANG . Antitumor and antibacterial activities of pyridyl Schiff base indium and dysprosium complexes. Chinese Journal of Inorganic Chemistry, 2025, 41(8): 1523-1532. doi: 10.11862/CJIC.20250073
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]
  Lijuan Wang , Yuping Ning , Jian Li , Sha Luo , Xiongfei Luo , Ruiwen Wang . Enhancing the Advanced Nature of Natural Product Chemistry Laboratory Courses with New Research Findings: A Case Study of the Application of Berberine Hydrochloride in Photodynamic Antimicrobial Films. University Chemistry, 2024, 39(11): 241-250. doi: 10.12461/PKU.DXHX202403017
18. [18]
  Caixia Lin , Ting Liu , Zhaojiang Shi , Hong Yan , Keyin Ye , Yaofeng Yuan . Innovative Experiment of Electrochemical Dearomative Spirocyclization of N-Acyl Sulfonamides. University Chemistry, 2025, 40(4): 359-366. doi: 10.12461/PKU.DXHX202406107
19. [19]
  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
20. [20]
  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

Get Citation

PDF

XML

Metrics

PDF Downloads(4)
Abstract views(2048)
HTML views(827)

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