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
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