Synthesis and Biological Evaluation of Novel N'-Arylmethylene-N-(4-benzoyloxy-thiazole-2-yl) Benzoylhydrazone Derivatives

doi:10.6023/cjoc201408036

Chin. J. Org. Chem. ›› 2015, Vol. 35 ›› Issue (2): 462-466.DOI: 10.6023/cjoc201408036 Previous Articles Next Articles

Notes

新型N'-芳基亚甲基-N-(4-取代苯甲酰氧基噻唑-2-基)取代苯甲酰腙的合成与生物活性

刘建超, 刘勇军, 贺红武

华中师范大学化学学院武汉 430079

收稿日期:2014-08-29 修回日期:2014-10-30 发布日期:2014-11-05
通讯作者: 贺红武 E-mail:he1208@mail.ccnu.edu.cn;liujc@mail.ccnu.edu.cn
基金资助:
国家重点基础研究发展规划(973计划, No. 2010CB126100)、国家自然科学基金(Nos. 21172090, 31000867)、教育部创新团队项目部分(No. IRT0953)资助项目.

Synthesis and Biological Evaluation of Novel N'-Arylmethylene-N-(4-benzoyloxy-thiazole-2-yl) Benzoylhydrazone Derivatives

Liu Jianchao, Liu Yongjun, He Hongwu

College of Chemistry, Central China Normal University, Wuhan 430079

Received:2014-08-29 Revised:2014-10-30 Published:2014-11-05
Supported by:
Project supported by the National Program on Key Basic Research Project (973 Program, No. 2010CB126100), the National Natural Science Foundation of China (Nos. 21172090, 31000867) and the Program for Changjiang Scholars and Innovatives Research Team in University (No. IRT0953).

1. Synthesis and Biological Evaluation of Novel N'-Arylmethylene-N-(4-benzoyloxy-thiazole-2-yl) Benzoylhydrazone Derivatives.PDF(24407KB)

Abstract

14 novel N'-arylmethylene-N-(4-benzoyloxy-thiazole-2-yl) benzoylhydrazone derivatives were designed and synthesized by incorporating the activated structural templets of thiazole and acylhydrazone. All the target compounds were characterized by ¹H NMR, IR, mass spectrometry and elemental analysis, and some of the compounds were confirmed by ¹³C NMR. Anti-tumor test results showed that the hydrazone compounds showed significant anti-tumor activity. These compounds were more active against the KB cell lines than the CNE2 cell lines. All synthesized compounds were screened by plate method in vitro for their fungicidal activity against Gibberella zeae, Thanatephorus cucumeris, Botrytis cinereapers, Alternaria solani, Alternaria alternate, and Colletotrichum orbiculare. In the 1.0×10^－4 g/mL concentration, some tested compounds exhibited middle-inhibitory activity of funguses.

Key words: thiazole, acylhydrazone, anticancer, fungicide

Cite this article

Liu Jianchao, Liu Yongjun, He Hongwu. Synthesis and Biological Evaluation of Novel N'-Arylmethylene-N-(4-benzoyloxy-thiazole-2-yl) Benzoylhydrazone Derivatives[J]. Chin. J. Org. Chem., 2015, 35(2): 462-466.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] Dayam, R.; Sanchez, T.; Clement, O.; Shoemaker, R.; Sei, S.; Neamati, N. J. Med. Chem. 2005, 48, 111.
[2] Li, F. Y.; Zhu, Q. Z.; Zhang, Y.; Feng, Y.; Leng, Y.; Zhang, A. Bioorg. Med. Chem. 2010, 18, 3875.
[3] Samir, B.; Wesam, K.; Ahmed, A. F. Eur. J. Med. Chem. 2007, 42, 948.
[4] Maienfisch, P.; Angst, M.; Brandl, F.; Fischer, W.; Hofer, D.; Kayser, H.; Kobel, W.; Rindlisbacher, A.; Senn, R.; Steinemann, A.; Widmer, H. Pest Manage. Sci. 2001, 57, 906.
[5] Liu, J. C.; Liang, Y.; He, H. W. Chin. Chem. Lett. 2013, 24, 233.
[6] Liu, J. C.; Liang, Y.; He, H. W. Chin. J. Org. Chem. 2013, 33, 1945 (in Chinese). (刘建超, 梁英, 贺红武, 有机化学, 2013, 33, 1945.)
[7] Hay, M. P.; Turcotte, S.; Flanagan, J. U.; Bonnet, M.; Chan, D. A.; Sutphin, P. D.; Nguyen, P.; Giaccia, A. J.; Denny, W. A. J. Med. Chem. 2010, 53, 787.
[8] Sahar, M. A. S. Eur. J. Med. Chem. 2010, 45, 4113.
[9] French, K.; Schrecengost, R. S.; Lee, B. D.; Kevin J.; French, K. J.; Schrecengost, R. S.; Lee, B. D.; Zhuang, Y.; Smith, S. N.; Eberly, J. L.; Yun, J. K.; Smith, C. D. Cancer Res. 2003, 63, 5962.
[10] Kumar, D.; Judge, V.; Narang, R.; Sangwan, S.; Clercq, E. D.; Balzarini, J.; Narasimhan, B. Eur. J. Med. Chem. 2010, 45, 2806.
[11] Gülhan, T. Z.; Zafer, A. K.; Ahmet, Ö. Eur. J. Med. Chem. 2010, 45, 2085.
[12] Huang, H.; Chen, Q.; Ku, X.; Meng, L.; Lin, L.; Wang, X.; Zhu, C.; Wang, Y.; Chen, Z.; Li, M.; Jiang, H.; Chen, K.; Ding J.; Liu, H. J. Med. Chem. 2010, 53, 3048.
[13] Liu, J. C.; Cui, Z. P.; He, H. W. Chin. J. Org. Chem. 2012, 32, 1925 (in Chinese). (刘建超, 崔泽平, 贺红武, 有机化学, 2012, 32, 1925.)
[14] Lv, P. C.; Zhou, C. F.; Chen, J.; Liu, P. G.; Wang, K. R.; Mao, W. J.; Li, H. Q.; Yang, Y.; Xiong, J.; Zhu, H. L. Bioorg. Med. Chem. 2010, 18, 314.
[15] Leite, A. C. L.; Lima, R. S. D.; Moreira, D. R. D. M.; Cardoso, M. V. D. O.; Brito, A. C. G. D.; Santos, L. M. F. D.; Hernandes, M. Z.; Kiperstok, A. C.; Lima, R. S. D.; Soares, M. B. P. Bioorg. Med. Chem. 2006, 14, 3749.

新型N'-芳基亚甲基-N-(4-取代苯甲酰氧基噻唑-2-基)取代苯甲酰腙的合成与生物活性

Synthesis and Biological Evaluation of Novel N'-Arylmethylene-N-(4-benzoyloxy-thiazole-2-yl) Benzoylhydrazone Derivatives

PDF

Supporting Info.

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Xiaoying Jia, Jiaxia Pu, Lirong Han, Qinghan Li. Research Progress in the Synthesis of Benzo[d]pentamembered Heterocyclic Thioethers Containing Two Heteroatoms [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 18-40.
[2]	Ruixia Cao, Yuping Jia. Synthesis and Biological Activity of Novel Pyrrolo[2,3-d]pyrimidine Derivatives Containing Coumarin [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3304-3311.
[3]	Weishu Zhang, Lifei Nie, Khurshed Bozorov, Haji Akber Aisa, Jiangyu Zhao. Synthesis of Diethyl 2,5-Diaminothiophene-3,4-dicarboxylate Derivatives and Antitumor Activity Study [J]. Chinese Journal of Organic Chemistry, 2023, 43(7): 2543-2552.
[4]	Meng Li, Dongguo Xia, Yunxiao Wang, Xiang Cheng, Jiexiu Gong, Yao Chen, Xianhai Lü. Design, Synthesis and Antifungal Bioactivity Evaluation of Thiazole Benzoate Derivatives [J]. Chinese Journal of Organic Chemistry, 2023, 43(2): 686-696.
[5]	Meng Liu, Yanru Huang, Xiaofei Sun, Lijun Tang. An “Aggregation-Induced Emission+Excited-State Intramolecular Proton Transfer” Mechanisms-Based Benzothiazole Derived Fluorescent Probe and Its ClO^–Recognition [J]. Chinese Journal of Organic Chemistry, 2023, 43(1): 345-351.
[6]	Xing Huang, Changhao Zhang, Hao Deng, Qingkun Shen, Hongyan Guo, Zheshan Quan, Zhiyong Li, Lili Jin. Synthesis and Antitumor Activity of Hederagenin Derivatives [J]. Chinese Journal of Organic Chemistry, 2022, 42(9): 2877-2887.
[7]	Jing Zhao, Zhe Jin, Run Wang, Xin'geng Zhang, Yingmei Han, Chun Hu, Xiaoping Liu, Chuanming Zhang, Liping Jin. Design, Synthesis and Anticancer Activity of 2-((Pyridin- 2-ylmethyl)thio)-1H-benzimidazole Derivatives [J]. Chinese Journal of Organic Chemistry, 2022, 42(7): 2172-2183.
[8]	Junzhe Yang, Zichao Xu, Chunpu Li, Yuanzheng Cheng, Hong Liu. Research Progress of Tropomyosin Receptor Kinase (TRK) Inhibitors [J]. Chinese Journal of Organic Chemistry, 2022, 42(7): 2055-2069.
[9]	Ming Yang, Danfeng Huang, Kehu Wang, Tongyu Han, Pengfei Zhao, Feng Wang, Junjiao Wang, Yingpeng Su, Yulai Hu. Silver-Catalyzed Synthesis of CF₃-Substituted 2-Imidazolines [J]. Chinese Journal of Organic Chemistry, 2022, 42(5): 1509-1519.
[10]	Mianyuan Wu, Yanchao Yu, Yang Liu, Jun You, Wenju Wu, Bo Liu. Synthesis and Application of a Novel Fluorescent Probe for Sequential Recognition Cu²⁺ and Glyphosate [J]. Chinese Journal of Organic Chemistry, 2022, 42(3): 803-811.
[11]	Yan Zeng, Lifei Nie, Chao Niu, Aytilla Mamatjan, Khurshed Bozorov, Jiangyu Zhao, Haji Akber Aisa. Synthesis and Biological Activities of Dihydrooxazolo[5,4-d]-pyrrolo[1,2-a]pyrimidinones [J]. Chinese Journal of Organic Chemistry, 2022, 42(2): 543-556.
[12]	Shu Chen, Yingying Shao, Xinhao Fu, Qingwu Chen, Xiaohua Du, Chengxia Tan. Design, Synthesis and Insecticidal Activities of Pyridyl Thiazole Diamide Compounds [J]. Chinese Journal of Organic Chemistry, 2022, 42(11): 3870-3879.
[13]	Yajun Mao, Xiangmin Shao, Yangjie Li, Ruimei Cao, Yali Feng, Guangyu Zhai. Research Progress on the Synthesis of Quercetin Derivatives [J]. Chinese Journal of Organic Chemistry, 2022, 42(11): 3588-3605.
[14]	Honglin Dai, Xiaojie Si, Lingling Chi, Hao Wang, Chao Gao, Zhengjie Wang, Limin Liu, Jiajie Ma, Fuqiang Yu, Hongmin Liu, Yu Ke, Qiurong Zhang. Synthesis and Antitumor Activity Evaluation of 2,4,6-Trisubstituted Quinazoline Derivatives Containing Thiazole Structure [J]. Chinese Journal of Organic Chemistry, 2022, 42(11): 3853-3862.
[15]	Shenghui Wang, Yongfeng Guan, Xiujuan Liu, Xinying Yuan, Guangxi Yu, Yinru Li, Yanbing Zhang, Jian Song, Wen Li, Saiyang Zhang. Design, Synthesis and Anticancer Activity Studies of Novel Quinoline-Indole Derivatives [J]. Chinese Journal of Organic Chemistry, 2021, 41(9): 3617-3624.