Citation: Lei Qiang, Qin Shangshang, Feng Cuining, Li Peipei, Zhang Xi, Long Yue. Synthesis and Biological Activities of 1, 3, 4-Oxadiazole Triazene Derivatives[J]. Chinese Journal of Organic Chemistry, ;2016, 36(2): 406-411. doi: 10.6023/cjoc201507004 shu

Synthesis and Biological Activities of 1, 3, 4-Oxadiazole Triazene Derivatives

Lei Qiang ^a ,
Qin Shangshang ^b ,
Feng Cuining ^a ,
Li Peipei ^a ,
Zhang Xi ^a ,
Long Yue ^a,*,,

a.
College of Chemistry and Molecular Engineering, Zhengzhou University, Zhengzhou 450001
b.
School of Pharmaceutical Sciences, Zhengzhou University, Zhengzhou 450001

Corresponding author: Long Yue, longyue@zzu.edu.cn
Received Date: 3 July 2015
Revised Date: 7 October 2015

Fund Project: the Science and Technology Planning Project of Henan Province 0624420031the Basic Research Development Program of Henan Province 022463001the National Natural Science Foundation of China J1210060

Figures(3)

11 novel 1, 3, 4-oxadiazole triazene derivatives were designed and synthesized by combination of triazenes and 1, 3, 4-oxadiazoles. All the target compounds were characterized by ¹H NMR, IR and HRMS. The antitumor activities of all compounds were screened by using thiazolylblue (MTT) assay in vitro, in which MGC803 cell lines and PC-3 cell lines were used as the test cancer cell. The results showed that compounds 2-(4-(3, 3-dimethyltriaz-1-en-1-yl)phenyl)-5-(4-methoxy-phenyl)-1, 3, 4-oxadiazole (b₄), 2-(4-(3, 3-dimethyltriaz-1-en-1-yl)phenyl)-5-(2-methoxyphenyl)-1, 3, 4-oxadiazole (b₉), 2-(4-(3, 3-dimethyltriaz-1-en-1-yl)phenyl)-5-(benzo[d][1, 3]dioxol-5-yl)-1, 3, 4-oxadiazole (b₁₀) and 2-(4-(3, 3-dimethyltriaz-1-en-1-yl)phenyl)-5-(pyridin-4-yl)-1, 3, 4-oxadiazole (b₁₁) exhibited higher activity against PC-3 cell than control compound dacarbazine (DTIC), and their IC₅₀ values were 74.145, 87.790, 87.327 and 104.875 μmol/L, respectively. But all compounds had little inhibition effect on MGC803 cell lines. All synthesized compounds were screened by broth dilution technique for their fungicidal activity against S. aureus and E. coli. The antibacterial activity results showed that all of compounds were inactive.
- triazenes,
- 1, 3, 4-oxadiazoles,
- synthesis,
- antitumor,
- antibacterial
1. [1]
  Zhang, X. H.; Chen, W. B. Asian J. Chem. 2013, 25, 9805.
2. [2]
  Zhu, C. S.; Chen, W. B. Asian J. Chem. 2013, 25, 7409.
3. [3]
  Chu, J.; Xie, X. H.; Yang, S. R.; Zhan, S. Z. Inorg. Chim. Acta 2014, 410, 191. doi: 10.1016/j.ica.2013.10.026
4. [4]
  Stefan, B.; Stefan, D.; Frank, L.; Nicholas, E. L.; Emma, L. S. Bioorg. Med. Chem. Lett. 2002, 12, 1849. doi: 10.1016/S0960-894X(02)00279-2
5. [5]
  Sun, H.; Wang, C. M.; Yang, Y. F.; Chen. P.; Wu, Y. D.; Zhang, X. H.; Huang, Y. J. Org. Chem. 2014, 79, 11863. doi: 10.1021/jo500807d
6. [6]
  Koji, T.; Mohammad A. A.; Naoyuki, H.; Johan, W.; Hiroshi, S.; Yoshitsugu, S.; Hayato, F.; Satoshi, S.; Mitsuhiro, A. J. Org. Chem. 2014, 79, 6366. doi: 10.1021/jo5009838
7. [7]
  Nan, G. M.; Zhou, J. Chin. J. Org. Chem. 2012, 32, 1695 (in Chinese). doi: 10.6023/cjoc1201311
8. [8]
  Zhou, J.; Yang, W. J.; Wang, B. J.; Ren, H. J. Angew. Chem., Int. Ed. 2012, 51, 12293. doi: 10.1002/anie.v51.49
9. [9]
  Simona, C.; Sabrina, F.; Giuseppe, S.; Maria, T. R.; Enzo, B.; Josef, J.; Stefania, D. A. Mol. Pharmacol. 2004, 66, 478.
10. [10]
  Reid, J. M.; Kuffel, M. J.; Miller, J. K.; Rios, R.; Ames, M. M. Clin. Cancer Res. 1999, 5, 2192.
11. [11]
  Marchesi, F.; Turriziani, M.; Tortorelli, G.; Awisati, G.; Torino, F.; Vecchis, L. D. Pharmacol. Res. 2007, 56, 275. doi: 10.1016/j.phrs.2007.08.003
12. [12]
  Yuichi, H.; Mitchel, S. B.; Russell, O. P. Cancer Res. 2001, 61, 1957
13. [13]
  Cledualdo, S. O.; Bruno, F. L.; Jose, M. B. F.; Jorge, G. F. L.; Petronio, F. A. F. Molecules 2012, 17, 10192. doi: 10.3390/molecules170910192
14. [14]
  Liu, J. C.; Wang, W. D.; He, H. W. Chin. J. Org. Chem. 2014, 34, 1447 (in Chinese). doi: 10.6023/cjoc201403013
15. [15]
  Sun, N. B.; Tong, J. Y.; Wu, H. K. Chin. J. Org. Chem. 2013, 33, 101 (in Chinese). doi: 10.6023/cjoc201208019
16. [16]
  Yu, W. Q.; Huang, G.; Zhang, Y. T.; Liu, H. X.; Dong, L. H.; Yu, X. J.; Li, Y. J.; Chang, J. B. J. Org. Chem. 2013, 78, 10337. doi: 10.1021/jo401751h
17. [17]
  Gao, Y. L.; Lin, X. F.; Han, F. F.; Bao, X. P. Chin. J. Org. Chem. 2011, 31, 1648 (in Chinese).
18. [18]
  Xu, Y.; Lei, P.; Ling, Y.; Wang, S. W.; Yang, X. L. Chin. J. Org. Chem. 2014, 34, 1118 (in Chinese). doi: 10.6023/cjoc201401034
19. [19]
  Clinical and Laboratory Standards Institute. 2012. Performance standards for antimicrobial susceptibility testing; 20th informational supplement. M100-S22. Clinical and Laboratory Standards Institute, Wayne, PA.
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]
  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
3. [3]
  Jiaming Xu , Yu Xiang , Weisheng Lin , Zhiwei Miao . Research Progress in the Synthesis of Cyclic Organic Compounds Using Bimetallic Relay Catalytic Strategies. University Chemistry, 2024, 39(3): 239-257. doi: 10.3866/PKU.DXHX202309093
4. [4]
  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
5. [5]
  Tianlong Zhang , Rongling Zhang , Hongsheng Tang , Yan Li , Hua Li . Online Monitoring and Mechanistic Analysis of 3,5-diamino-1,2,4-triazole (DAT) Synthesis via Raman Spectroscopy: A Recommendation for a Comprehensive Instrumental Analysis Experiment. University Chemistry, 2024, 39(6): 303-311. doi: 10.3866/PKU.DXHX202312006
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]
  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
8. [8]
  Linjie ZHU , Xufeng LIU . Synthesis, characterization and electrocatalytic hydrogen evolution of two di-iron complexes containing a phosphine ligand with a pendant amine. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 939-947. doi: 10.11862/CJIC.20240416
9. [9]
  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
10. [10]
  Shuhui Li , Rongxiuyuan Huang , Yingming Pan . Electrochemical Synthesis of 2,5-Diphenyl-1,3,4-Oxadiazole: A Recommended Comprehensive Organic Chemistry Experiment. University Chemistry, 2025, 40(5): 357-365. doi: 10.12461/PKU.DXHX202407028
11. [11]
  Aidang Lu , Yunting Liu , Yanjun Jiang . Comprehensive Organic Chemistry Experiment: Synthesis and Characterization of Triazolopyrimidine Compounds. University Chemistry, 2024, 39(8): 241-246. doi: 10.3866/PKU.DXHX202401029
12. [12]
  Jianyu Qin , Yuejiao An , Yanfeng Zhang . In Situ Assembled ZnWO₄/g-C₃N₄ S-Scheme Heterojunction with Nitrogen Defect for CO₂ Photoreduction. Acta Physico-Chimica Sinica, 2024, 40(12): 2408002-. doi: 10.3866/PKU.WHXB202408002
13. [13]
  Yahui HAN , Jinjin ZHAO , Ning REN , Jianjun ZHANG . Synthesis, crystal structure, thermal decomposition mechanism, and fluorescence properties of benzoic acid and 4-hydroxy-2, 2′: 6′, 2″-terpyridine lanthanide complexes. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 969-982. doi: 10.11862/CJIC.20240395
14. [14]
  Changqing MIAO , Fengjiao CHEN , Wenyu LI , Shujie WEI , Yuqing YAO , Keyi WANG , Ni WANG , Xiaoyan XIN , Ming FANG . Crystal structures, DNA action, and antibacterial activities of three tetranuclear lanthanide-based complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2455-2465. doi: 10.11862/CJIC.20240192
15. [15]
  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
16. [16]
  Yadan Luo , Hao Zheng , Xin Li , Fengmin Li , Hua Tang , Xilin She . Modulating reactive oxygen species in O, S co-doped C₃N₄ to enhance photocatalytic degradation of microplastics. Acta Physico-Chimica Sinica, 2025, 41(6): 100052-. doi: 10.1016/j.actphy.2025.100052
17. [17]
  Caixia Lin , Zhaojiang Shi , Yi Yu , Jianfeng Yan , Keyin Ye , Yaofeng Yuan . Ideological and Political Design for the Electrochemical Synthesis of Benzoxathiazine Dioxide Experiment. University Chemistry, 2024, 39(2): 61-66. doi: 10.3866/PKU.DXHX202309005
18. [18]
  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
19. [19]
  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
20. [20]
  Yongqing Kuang , Jie Liu , Jianjun Feng , Wen Yang , Shuanglian Cai , Ling Shi . Experimental Design for the Two-Step Synthesis of Paracetamol from 4-Hydroxyacetophenone. University Chemistry, 2024, 39(8): 331-337. doi: 10.12461/PKU.DXHX202403012

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(955)
HTML views(123)

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