Citation: Zhang Luye, Zhang Yang, Bao Chongnan, Yang Peng, Li Erdong, Meng Yaqi, Cui Fei, Zhou Rui, Huang Shiyu, Zheng Jiaxin, Shan Lihong, Liu Hongmin, Zhang Qiurong. Synthesis and Antitumor Activity of Novel 1, 3-Disubstituted Pyridazinone Derivatives[J]. Chinese Journal of Organic Chemistry, ;2020, 40(3): 794-800. doi: 10.6023/cjoc201908012 shu

Synthesis and Antitumor Activity of Novel 1, 3-Disubstituted Pyridazinone Derivatives

Zhang Luye ^a,b ,
Zhang Yang ^a,b ,
Bao Chongnan ^a,b ,
Yang Peng ^a,b ,
Li Erdong ^a,b ,
Meng Yaqi ^a,b ,
Cui Fei ^a,b ,
Zhou Rui ^a,b ,
Huang Shiyu ^a,b ,
Zheng Jiaxin ^a,b,, ,
Shan Lihong ^a,b,, ,
Liu Hongmin ^a,b,c,d,, ,
Zhang Qiurong ^a,b,d,,

a.
School of Pharmaceutical Sciences, Zhengzhou University, Zhengzhou 450001
b.
Collaborative Innovation Center of New Drug Research and Safety Evaluation, Zhengzhou 450001
c.
State Key Laboratory of Esophageal Cancer Prevention & Treatment, Zhengzhou University y, Zhengzhou 450052
d.
Key Laboratory of Advanced Drug Preparation Technologies, Ministry of Education of China, Zhengzhou 450001

Corresponding author: Zheng Jiaxin, zqr409@yeah.net Shan Lihong, shlh@zzu.edu.cn Liu Hongmin, liuhm@zzu.edu.cn Zhang Qiurong, zjx1224@163.com
Received Date: 8 August 2019
Revised Date: 11 October 2019
Available Online: 21 November 2019
Fund Project: the Natural Science Foundation of Henan Province No. 182300410321the Openning Fund from State Key Laboratory of Esophageal Cancer Prevention & Treatment No. K2020000XProject supported by the National Natural Science Foundation of China (No. 81430085), the Natural Science Foundation of Henan Province (No. 182300410321), and the Openning Fund from State Key Laboratory of Esophageal Cancer Prevention & Treatment (No. K2020000X)Project supported by the National Natural Science Foundation of China No. 81430085

Figures(2)

In order to find more efficient and low toxicity antitumor drugs, a series of novel 1, 3-disubstituted pyridazinone derivatives were synthesized and evaluated for their antiproliferative activities against four human cancer cell lines (MCF-7, PC-3, SW-620 and HGC-27) in vitro. The results showed that most compounds had good antiproliferative activities, especially 2-(4-(4-bromophenyl)-1-oxo-tolylazine-2(1H)-yl)-N-(2-fluorophenyl)acetamide (5g) exhibited better antiproliferative activities with IC₅₀ value of 6.01 μmol/L. In a nutshell, this work provided clues to discover antitumor agent based on the quinazoline scaffold.
- pyridazinederiv,
- ative,
- synthesis,
- antiproliferative activity
1. [1]
  Li N., Xin J. C., Ma Q. S., Li E. D., Meng Y. Q., Bao C. N., Yang P., Song P. P., Cui F., Cheng P. J., Gu Y. F., Zhao P. R., Ke Y., Liu H. M., Zhang Q. R.Chin. J. Org. Chem., 2018, 38:665(in Chinese).
2. [2]
  Duan Y. D., Jiang Y. Y., Guo F. X., Chen L. X., Xu L. L., Zhang W., Liu B.Fitoterapia, 2019, 135:114. doi: 10.1016/j.fitote.2019.04.012
3. [3]
  Jayaraj G., Sherlin H. J., Ramani P., Don K. R., Santhanam A., Sukumaran G., Ramasubramanian A.J. Oral Maxil. Surg., 2019, 31:228.
4. [4]
  Ronald C., Chen M. D. M. P. H.Urol. Oncol., 2019, 5:1.
5. [5]
  Zhang X., Zhu Y., Dong S., Zhang A., Lu Y., Li Y., Lv S., Zhang J.Life Sci., 2019, 232:1165.
6. [6]
  Wang C. J., Cao Q. P., Yang H., Song P.P., Xue D. Q., Cui F., Gu Y. F., Zhang X. S., Tian Y. N., Zhang Q. R., Liu H. M.Chin. J. Org. Chem., 2016, 36:1626(in Chinese).
7. [7]
  Li J., Pan H., Qiao S., Li Y., Wang J., Liu W., Pan W.Int. J. Biol. Macromol., 2019, 134:63. doi: 10.1016/j.ijbiomac.2019.05.031
8. [8]
  Kong K., Zhang J., Zhao P., Chen J., Chen Y.Tetrahedron, 2017, 73:6742. doi: 10.1016/j.tet.2017.10.028
9. [9]
  Zhang S., Zhao Y., Liu Y., Chen D., Lan W., Zhao Q., Dong C., Xia L., Gong P.Eur. J. Med. Chem., 2010, 45:3504. doi: 10.1016/j.ejmech.2010.05.016
10. [10]
  Lu X., Peng Y., Wang C., Yang J., Bao X., Dong Q., Zhao W., Tan W., Dong X.Eur. J. Med. Chem., 2017, 138:384. doi: 10.1016/j.ejmech.2017.06.031
11. [11]
  Prakash O., Aneja D. K., Hussain K., Kumar R., Arora S., Sharma C., Aneja K. R.J. Heterocycl. Chem., 2012, 49:1091. doi: 10.1002/jhet.943
12. [12]
  Hashash M. A. E., Dalal B. G., Nayera A. W., Mohamed A. K.J. Chem. Eng. Process Technol., 2014, 5:4.
13. [13]
  Sun X. Y., Hu C., Deng X. Q., Wei C. X., Sun Z. G., Quan Z. S.Eur. J. Med. Chem., 2010, 45:4807. doi: 10.1016/j.ejmech.2010.07.049
14. [14]
  Zhang H., Zhang H., Tian Y., Quan Z.Chin. J. Org. Chem., 2017, 37:2322(in Chinese).
15. [15]
  Xin J. C., Li N., Ma Q.S., Li E.D., Meng Y. Q., Ke Y., Liu H. M., Zhang Q. R.Chin. J. Org. Chem., 2018, 38:451(in Chinese).
16. [16]
  Boraei A. T. A., Ashour H. K., El Tamany E. S. H., Abdelmoaty N., El-Falouji A. I., Gomaa M. S.Bioorg. Chem., 2019, 85:293. doi: 10.1016/j.bioorg.2018.12.039
17. [17]
  Mozafari R., Heidarizadeh F.Polyhedron, 2019, 162:263. doi: 10.1016/j.poly.2019.01.065
18. [18]
  Ruiz-Schutz V. C., Gomes L. M., Mariano R. C., Almeida D. V. P., Maluf F. C., Schutz F. A.Crit. Rev. Oncol. Hematol., 2019, 141:163. doi: 10.1016/j.critrevonc.2019.06.012
19. [19]
  To K. K., Poon D. C., Wei Y., Wang F., Lin G., Fu L. W.Biochem. Pharmacol., 2015, 97:27. doi: 10.1016/j.bcp.2015.06.034
20. [20]
  Yang H. M., Park C. W., Park S., Kim J. D.Colloids Surf., B, 2018, 161:183. doi: 10.1016/j.colsurfb.2017.10.049
21. [21]
  Marochkin I. I., Dorofeeva O. V.Comput. Theor. Chem., 2012, 991:182. doi: 10.1016/j.comptc.2012.04.018
22. [22]
  Rodriguez-Hernandez D., Barbosa L. C. A., Demuner A. J., Ataide Martins J. P., Fischer L., Csuk R.Eur. J. Med. Chem., 2019, 168:436. doi: 10.1016/j.ejmech.2019.02.057
23. [23]
  Oteyza D. G., Garcia-Lekue A., Vilas-Varela M., Merino-Diez N., Carbonell-Sanroma E., Corso M., Vasseur G., Rogero C., Guitian E., Pascual J. I., Ortega J. E., Wakayama Y., Pena D.ACS Nano, 2016, 10:9000. doi: 10.1021/acsnano.6b05269
24. [24]
  Zhai L., Zhang Y. L., Kang J. S., Oelschlaeger P., Xiao L., Nie S. S., Yang K. W.ACS Med. Chem. Lett., 2016, 7:413. doi: 10.1021/acsmedchemlett.5b00495
25. [25]
  Modh R. P., Kumar S. P., Jasrai Y. T., Chikhalia K. H.Arch. Pharm. (Weinheim), 2013, 11:346.
26. [26]
  Ma L., Li S., Zheng H., Chen J., Lin L., Ye X., Chen Z., Xu Q., Chen T., Yang J., Qiu N., Wang G., Peng A., Ding Y., Wei Y., Chen L.Eur. J. Med. Chem., 2011, 46:2003. doi: 10.1016/j.ejmech.2011.02.033
27. [27]
  Li Q., Chen P., Yang H., Luo M., You W., Zhao P.Chem. Pap., 2017, 72:651.
28. [28]
  Kumar R., Kaur M., Bahia M. S., Silakari O.Eur. J. Med. Chem., 2014, 80:83. doi: 10.1016/j.ejmech.2014.04.030
29. [29]
  Wang G. B., Wang L. F., Li C. Z., Sun J., Zhou G. M., Yang D. C.Res. Chem. Intermed., 2011, 38:77.
30. [30]
  Wang G., Peng Z., Wang J., Li X., Li J.Eur. J. Med. Chem., 2017, 125:423. doi: 10.1016/j.ejmech.2016.09.067
31. [31]
  Wang J. H., Luo T. W., Li S. B., Zhang Y. B., Wang C. J., Zhao J.Curr. Med. Chem., 2013, 20:4070. doi: 10.2174/09298673113209990187
1. [1]
  Bin SUN , Heyan JIANG . Glucose-modified bis-Schiff bases: Synthesis and bio-activities in Alzheimer′s disease therapy. Chinese Journal of Inorganic Chemistry, 2025, 41(7): 1338-1350. doi: 10.11862/CJIC.20240428
2. [2]
  Lixing ZHANG , Yaowen WANG , Xu HAN , Junhong ZHOU , Jinghui WANG , Liping LI , Guangshe LI . Research progress in the synthesis of fluorine-containing perovskites and their derivatives. Chinese Journal of Inorganic Chemistry, 2025, 41(9): 1689-1701. doi: 10.11862/CJIC.20250007
3. [3]
  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
4. [4]
  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
5. [5]
  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
6. [6]
  Ying Chen , Ronghua Yan , Weiyan Yin . Research Progress on the Synthesis of Metal Single-Atom Catalysts and Their Applications in Electrocatalytic Hydrogen Evolution Reactions. University Chemistry, 2025, 40(9): 344-353. doi: 10.12461/PKU.DXHX202503066
7. [7]
  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
8. [8]
  Xinyi Zhang , Kai Ren , Yanning Liu , Zhenyi Gu , Zhixiong Huang , Shuohang Zheng , Xiaotong Wang , Jinzhi Guo , Igor V. Zatovsky , Junming Cao , Xinglong Wu . Progress on Entropy Production Engineering for Electrochemical Catalysis. Acta Physico-Chimica Sinica, 2024, 40(7): 2307057-0. doi: 10.3866/PKU.WHXB202307057
9. [9]
  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
10. [10]
  Chunling Qin , Shuang Chen , Hassanien Gomaa , Mohamed A. Shenashen , Sherif A. El-Safty , Qian Liu , Cuihua An , Xijun Liu , Qibo Deng , Ning Hu . Regulating HER and OER Performances of 2D Materials by the External Physical Fields. Acta Physico-Chimica Sinica, 2024, 40(9): 2307059-0. doi: 10.3866/PKU.WHXB202307059
11. [11]
  Qing ZHANG , Kexin ZHOU , Yanjun GUO , Guangjun CHEN , Bai HE , Bo YU , Songshan JIANG , Guoyuan YUAN , Huidong QIU . Preparation, functional modification, and applications of Fe₃O₄ nanoparticles. Chinese Journal of Inorganic Chemistry, 2026, 42(7): 1383-1411. doi: 10.11862/CJIC.20250344
12. [12]
  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
13. [13]
  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
14. [14]
  Longfei MA , Fang SI , Congjie PAN , Xinhua WANG . Synthesis and crystal structure of extended tetrathiafulvalene derivatives and cupric bromide charge transfer complexes. Chinese Journal of Inorganic Chemistry, 2026, 42(6): 1229-1236. doi: 10.11862/CJIC.20250355
15. [15]
  Mengyang LI , Zhonghao NIU , Hao XU , Jingli XIE . One-pot synthesis of 4H-pyran derivatives catalyzed by viologen-modified metal-organic frameworks. Chinese Journal of Inorganic Chemistry, 2026, 42(7): 1513-1522. doi: 10.11862/CJIC.20250205
16. [16]
  Chunyan Hu , Wei Wang , Zewei Mao , Mei Zhang , Lei Zhang , Yuping Lin . Three-stage progressive teaching reform and practice in organic chemistry experiments for pharmacy undergraduates: synthesis of coumarin-chalcone derivatives. University Chemistry, 2026, 41(7): 282-289. doi: 10.12461/PKU.DXHX202505011
17. [17]
  Jiaxuan YANG , Chenfa DENG , Jingyang LIU , Chenzexi XU , Hongxin CHEN , Yahui ZHU , Ying LI , Shuhua WANG , Rongping ZHOU , Chao CHEN . Advances in selective hydrogenation of α, β-unsaturated aldehydes/ketones catalyzed by metal-organic frameworks and their derivatives: A review. Chinese Journal of Inorganic Chemistry, 2025, 41(10): 1973-2010. doi: 10.11862/CJIC.20250175
18. [18]
  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
19. [19]
  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
20. [20]
  Chengyan XU , Jiangnan YU , Yu LI , Xizhen PAN , Yinlin HOU , Wenmin WANG . Synthesis, structure, and bioactivity of a Ho₄ complex bridged by azide group. Chinese Journal of Inorganic Chemistry, 2026, 42(7): 1453-1462. doi: 10.11862/CJIC.20260033

Get Citation

PDF

XML

Metrics

PDF Downloads(12)
Abstract views(1902)
HTML views(293)

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