Chinese Journal of Organic Chemistry >
Synthesis and Biological Activity of Benzo[h]quinolinium Hydrazine Compounds
Received date: 2018-05-17
Revised date: 2018-06-05
Online published: 2018-07-16
Supported by
Project supported by the National Natural Science Foundation of China (Nos. 21605039, 21702051), the Key Scientific Research Project of Henan Provinc (Nos. 18A150009, 17A350006), the Henan Normal University Science Foundation for Young Scholars (No. 2016QK10)
Quinoline derivatives, aryl hydrazines and hydrazide compounds have significant biological activities. Benzo[h] quinoline derivatives were synthesized from 1-naphthylamine, substituted benzaldehyde and methyl pyruvate by Doebner-Miller reaction. After the ester was reduced, the corresponding aldehyde was obtained by oxidation. Benzo[h] quinolinium and quinoline hydrazide compounds were synthesized by reacting benzo[h] quinoline formaldehyde with hydrazine salts and hydrazides, respectively. The preliminary activity data showed that most of the compounds exhibited significant inhibitory activities against cycle protein 25B (CDC 25B) and protein tyrosine phosphatase PTP 1B.
Key words： Benzo[h]quinoline derivatives; hydrazone; hydrazide; CDC 25B; PTP 1B; inhibitory activity
Shi Lei , Xu Jingjing , Bi Jingjing , Zhang Zhiguo , Liu Tongxin , Yang Xiaolan , Zhang Guisheng . Synthesis and Biological Activity of Benzo[h]quinolinium Hydrazine Compounds[J]. Chinese Journal of Organic Chemistry, 2018 , 38(11) : 3016 -3025 . DOI: 10.6023/cjoc201805038
[1] Abner, E.; Stoszko, M.; Zeng, L.; Chen, H. C.; Izquierdo-Bouldstridge, A.; Konuma, T.; Zorita, E.; Fanunza, E.; Zhang, Q.; Mahmoudi, T.; Zhou, M. M.; Filion, G. J.; Jordan, A. J. Virol. 2018, 92, 10.
[2] Kwon, S.; Lee, Y.; Jung, Y.; Kim, J. H.; Baek, B.; Lim, B.; Lee, J.; Kim, I.; Lee, J. Eur. J. Med. Chem. 2018, 148, 116.
[3] Cai, Y.; Liu, H.; Chen, H. Chem. Biol. Drug Des. 2018, 91, 805.
[4] Baba, A.; Kawamura, N.; Makino, H. J. Med. Chem. 1996, 39, 5176.
[5] Chopra, R.; Chibale, K.; Singh, K. Eur. J. Med. Chem. 2018, 148, 39.
[6] Wang, W. Q.; Huang, L.; Cui, P.; Wu, Q. Y. Chin. J. Org. Chem. 2016, 36, 1065(in Chinese). (汪万强, 黄琳, 崔萍, 吴琼友, 有机化学, 2016, 36, 1065.)
[7] Men, Y.; Dong, J. H.; Wang, S.; Xu, X. X. Org. Lett. 2017, 19, 6712.
[8] Roberta, R. S.; Jose, M. F. S.; Bianca, C. C. Bioorg. Med. Chem. Lett. 2015, 25, 2309.
[9] Gross, D. J.; Weiss, L.; Reibstein, I. H. Int. Immunopharcol. 2001, 1, 115.
[10] Li, K.; Li, Y.; Zhou, D. Bioorg. Med. Chem. 2016, 24, 1889.
[11] Nagabhushana, N.; Jurupula, R.; Udayakumar, D. J. Fluorine Chem. 2016, 183, 59.
[12] Rita, C. C. C.; Wagner, A. M.; Tayara, P. S. Bioorg. Med. Chem. Lett. 2016, 26, 1881.
[13] Ravikumar, C.; Joe, I. H.; Jayakumar, V. S. Chem. Phys. Lett. 2008, 460, 552.
[14] Xiang, Y.; Tong, A. J.; Jin, P. Y; Ju, Y. Org. Lett. 2006, 8, 2863.
[15] Özkay, Y.; Tunali, Y.; Karaca, H.; IsIkdag, I. Eur. J. Med. Chem. 2010, 45, 3293.
[16] Du, H.; Fan. Y. J.; Yang, L.; Bao, X. P. Chin. J. Org. Chem. 2018, 38, 531(in Chinese). (杜欢, 范冶江, 杨岚, 鲍小平, 有机化学, 2018, 38, 531.)
[17] Liu, J. C.; Liu. Y. J.; He, H. W. Chin. J. Org. Chem. 2015, 35, 462(in Chinese). (刘建超, 刘勇军, 贺红武, 有机化学, 2015, 35, 462.)
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