Synthesis and Protein Tyrosine Phosphatase 1B (PTP1B) Inhibitory Activity Evaluation of Novel N-Acylhydrazone Derivatives Containing Carbazole and Aromatic Ring/Aromatic Fused Heterocycle

doi:10.6023/cjoc202105032

Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (9): 3593-3607.DOI: 10.6023/cjoc202105032 Previous Articles Next Articles

ARTICLES

新型含咔唑环和芳环/芳稠杂环的N-酰腙衍生物的合成及蛋白酪氨酸磷酸酶1B (PTP1B)抑制活性评价

李英俊^a^,^*(), 林乐弟^a, 刘季红^b, 高立信^c, 盛丽^c, 靳焜^d, 刘雪洁^a, 杨鸿境^a, 李佳^c^,^*()

a 辽宁师范大学化学化工学院辽宁大连 116029
b 大连理工大学化学分析测试中心辽宁大连 116023
c 中国科学院上海药物研究所国家新药筛选中心药物研究国家重点实验室上海 201203
d 大连理工大学精细化工国家重点实验室辽宁大连 116012

收稿日期:2021-05-17 修回日期:2021-06-21 发布日期:2021-07-12
通讯作者: 李英俊, 李佳
基金资助:
辽宁省自然科学基金(20102126)

Synthesis and Protein Tyrosine Phosphatase 1B (PTP1B) Inhibitory Activity Evaluation of Novel N-Acylhydrazone Derivatives Containing Carbazole and Aromatic Ring/Aromatic Fused Heterocycle

Yingjun Li^a(), Ledi Lin^a, Jihong Liu^b, Lixin Gao^c, Li Sheng^c, Kun Jin^d, Xuejie Liu^a, Hongjing Yang^a, Jia Li^c()

a College of Chemistry and Chemical Engineering, Liaoning Normal University, Dalian, Liaoning 116029
b Chemistry Analysis and Inspection Center, Dalian University of Technology, Dalian, Liaoning 116023
c State Key Laboratory of Drug Research, National Center for Drug Screening, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203
d State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian, Liaoning 116012

Received:2021-05-17 Revised:2021-06-21 Published:2021-07-12
Contact: Yingjun Li, Jia Li
Supported by:
Natural Science Foundation of Liaoning Province(20102126)

1. .pdf(3197KB)

Abstract

In order to find more efficient and low toxicity protein tyrosine phosphatase 1B (PTP1B) inhibitors, a series of novel N-acylhydrazone derivatives containing carbazole and aromatic ring/aromatic fused heterocycle 6~8 and 11 were designed and synthesized. Their structures and configurations were confirmed by IR, ¹H NMR, ¹³C NMR, two-dimensional NMR spectra (including ¹H-¹H COSY and NOESY) and elemental analysis. The inhibitory activities of all the target compounds against PTP1B were evaluated. The experimental results indicated that all the target compounds had potent inhibitory activity against PTP1B, and the activities were higher than the control drug oleanolic acid except for N'-[9-(2-chlorothiazole-5-methyl)carbazole-3-methylene]-2-phenylaminoacethydrazide (6a), N'-[9-(2-chlorothiazole-5-methyl)carbazole-3-methylene]- 2-(4-methylphenylamino)acethydrazide (6b), N'-[9-(2-chlorothiazole-5-methyl)carbazole-3-methylene]-2-(3-nitrophenylamino)acethydrazide (6g) and N'-[9-(2-chlorothiazole-5-methyl)carbazole-3-methylene)-2-(4-nitrophenylamino) acethydrazide (6h). Among them, N,N'-[(9-butylcarbazolyl)-3,6-dimethylene]-2,2'-[di(4-nitrophenylamino)]bisacetohydrazide (11b) had the highest inhibitory activity against PTP1B with IC₅₀ of (0.89±0.06) μmol/L. Molecular docking was used to study the bind of the representative target compounds N'-[9-(2-chlorothiazole-5-methyl)carbazole-3-methylene]-2-(4-bromophenylamino)acethydrazide (6d), N'-[9-(2-chlorothiazole-5-methyl)carbazole-3-methylene)-2-((2-(1-naphthyloxy)methyl)benzimidazol-1-yl)- acethydrazide (7f) and 11b with PTP1B enzyme, respectively.

Key words: PTP1B inhibitor, carbazole, N-actylhydrazone, synthesis, molecular docking

Cite this article

Yingjun Li, Ledi Lin, Jihong Liu, Lixin Gao, Li Sheng, Kun Jin, Xuejie Liu, Hongjing Yang, Jia Li. Synthesis and Protein Tyrosine Phosphatase 1B (PTP1B) Inhibitory Activity Evaluation of Novel N-Acylhydrazone Derivatives Containing Carbazole and Aromatic Ring/Aromatic Fused Heterocycle[J]. Chinese Journal of Organic Chemistry, 2021, 41(9): 3593-3607.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

Fig. & Tab. 16

References 59

[1]	Ji, W. J.; Chen, X. L.; Lv, J.; Wang, M.; Ren, S. T.; Yuan, B. X.; Wang, B.; Chen, L. N. Int. J. Endocrinol. 2014, 2014, 312452.
[2]	Yang, L. L.; Chen, F.; Gao, C.; Chen, J. B.; Li, J. Y.; Liu, S. Y.; Zhang, Y. Y.; Wang, Z. Y.; Qian, S. J. Enzyme Inhib. Med. Chem. 2020, 35, 152.
[3]	Salinas-Arellano, E.; Pérez-Vásquez, A.; Rivero-Cruz, I.; Torres- Colin, R.; González-Andrade, M.; Rangel-Grimaldo, M.; Mata, R. Molecules 2020, 25, 3530. doi: 10.3390/molecules25153530
[4]	Krishnan, N.; Konidaris, K. F.; Gasser, G.; Tonks, N. K. J. Biol. Chem. 2018, 293, 1517.
[5]	Guo, S. J.; Wang, L. J.; Chen, D.; Jiang, B. RSC Adv. 2020, 10, 3429. doi: 10.1039/C9RA10660J
[6]	Costa, G. C.; Montagnoli, T. L.; Silva, M. M. C.; Gamba, L. E. R.; Alves, B. E. O.; Silva, M. M. C.; Trachez, M. M.; Nascimento, J. H. M.; Pimentel-Coelho, P. M.; Mendez-Otero, R.; Lima, L. M.; Barreiro, E. J.; Sudo, R. T.; Zapata-Sudo, G. Drug Des. Dev. Ther. 2020, 14, 3337. doi: 10.2147/DDDT.S258459
[7]	Lu, Y. J.; Zhao, Z. D.; Chen, Y. X.; Wang, J.; Xu, S. C.; Gu, Y. J. Asian Nat. Prod. Res. 2021, 23, 545.
[8]	Liu, K.; Ding, Y. Y.; Kang, C. M. Pharm. Chem. J. 2020, 54, 345. doi: 10.1007/s11094-020-02215-w
[9]	Mota, F. V. B.; Neta, M. S. A.; Franco, E. S.; Bastos, I. V. G. A.; Correia da Araújo, L. C; Cabral da Silva, S.; Bezerra de Oliveira, T.; Souza, E. K.; Moraes de Almeida, V.; Ximenes, R. M.; Maia, M. B. S.; Junior, F. J. B. M.; Marchand, P.; Rodolfo de Faria, A.; Gonçalves da Silva, T. Med. Chem. Commun. 2019, 10, 1916. doi: 10.1039/C9MD00276F
[10]	Sulaiman, A. T.; Sarsam, S. W. Iraqi J. Pharm. Sci. 2020, 29, 207.
[11]	Aarjane, M.; Aouidate, A.; Slassi, S.; Amine, A. Arab. J. Chem. 2020, 13, 6236.
[12]	Senthilkumar, S.; Seralathan, J.; Muthukumaran, G. J. Mol. Struct. 2021, 1226, 129354. doi: 10.1016/j.molstruc.2020.129354
[13]	Yang, Z.-B.; Li, P.; He, Y. J. Molecules 2019, 24, 3766. doi: 10.3390/molecules24203766
[14]	Silva, M. F.; Lima, E. T.; Pruccoli, L.; Castro, N. G.; Guimarães, M. J. R.; Silva, F. M. R.; Nadur, N. F.; Luiz de Azevedo, L.; Kümmerle, A. E.; Guedes, I. A.; Dardenne, L. E.; Gontijo, V. S.; Tarozzi, A.; Viegas Jr, C. Molecules 2020, 25, 3165. doi: 10.3390/molecules25143165
[15]	Palwankar, S. M.; Kale, P. P.; Kadu, P. K.; Prabhavalkar, K. J. Rep. Pharm. Sci. 2020, 9, 79.
[16]	Aminah, N. S.; Thant, T. M.; Kristanti, A. N.; Ramadhan, R.; Aung, H. T.; Takaya, Y. Nat. Prod. Commun. 2020, 14, 1.
[17]	Chena, Y. M.; Cao, N. K.; Lv, H. N.; Zeng, K. W.; Yuan, J. Q.; Guo, X. Y.; Zhao, M. B.; Tu, P. F.; Jiang, Y. Phytochemistry 2020, 170, 112186. doi: 10.1016/j.phytochem.2019.112186
[18]	Liu, Y. H.; Wu, Y. B.; Sun, L. Q.; Gu, Y. X.; Hu, L. X. Eur. J. Med. Chem. 2020, 191, 112181. doi: 10.1016/j.ejmech.2020.112181
[19]	Yamashita, S.; Honda, R.; Fukuoka, M.; Kimurab, T.; Hosokawa-Mutoc, J.; Kuwataa, K. Prion 2020, 14, 42. doi: 10.1080/19336896.2020.1714372 pmid: 31971853
[20]	Wang, W. B.; Zhou, Z. G.; Zhou, X, H.; Chen, L. M.; Bie, S.; Jing, Z. J. AMB Expr. 2020, 10, 148. doi: 10.1186/s13568-020-01074-8
[21]	Taheri, B.; Taghavi, M.; Zarei, M.; Chamkouri, N.; Mojaddami, A. Bull. Chem. Soc. Ethiop. 2020, 34, 377.
[22]	Balakrishnan, R.; Vijayraja, D.; Jo, S.-H.; Ganesan, P.; Su-Kim, I.; Choi, D.-K. Antioxidants 2020, 9, 101. doi: 10.3390/antiox9020101
[23]	Sadeghian, B.; Sakhteman, A.; Faghih, Z.; Nadri, H.; Edraki, N.. IRaji, A.; Sadeghian, I.; Rezaei, Z. J. Mol. Struct. 2020, 1221, 128793.
[24]	Telehoiu, A. T.; Nuţă, D. C.; Căproiu, M. T.; Dumitrascu, F.; Zarafu, I.; Ioniţă, P.; Badiceanu, C. D.; Avram, S.; Chifiriuc, M. C.; Bleotu, C.; Limban, C. Molecules 2020, 25, 266. doi: 10.3390/molecules25020266
[25]	Sutkuvienė, S.; Sakalauskaitė, S.; Kuliešienė, N.; Ragelienė, L.; Daugelavičius, R. Biologija 2020, 66, 80.
[26]	Caruso, A.; Ceramella, J.; Iacopetta, D.; Saturnino, C.; Mauro, M. V.; Bruno, R.; Aquaro, S.; Sinicropi, M. S. Molecules 2019, 24, 1912. doi: 10.3390/molecules24101912
[27]	Ramalingam, A.; Sarvanan, J. Int. J. Pharm. Investigation 2020, 10, 594.
[28]	Du, L. F.; Wang, X. Y.; Cui, G. N.; Xu, B. L. Bioorg. Med. Chem. 2021, 29, 115878.
[29]	Alsantali, R. I.; Hussein, E. M.; Obaid, R. J.; Morad, M.; Altass, H. M.; Alharbi, A.; Hameed, A. M.; Jassas, R. S.; Abourehab, M. A. S.; Asghar, B. H.; Moussa, Z.; Ahmed, S. A. Arab. J. Chem. 2020, 13, 5451.
[30]	Wu, D. X.; Liu, M. H.; Li, Z.; Dang, M. M.; Liu, X. P.; Li, J. M.; Huang, L.; Ren, Y. G.; Zhang, Z.; Liu, W. D.; Liu, A. P. Heterocycl. Commun. 2019, 25, 8. doi: 10.1515/hc-2019-0003
[31]	Abdel-Galil, E.; Girges, M. M.; Said, G. E. ChemistrySelect 2020, 5, 3075. doi: 10.1002/slct.v5.10
[32]	Shinde, V.; Mahulikar, P.; Mhaske, P. C.; Chakraborty, S.; Choudhari, A.; Phalle, S.; Choudhari, P.; Sarkar, D. Med. Chem. Res. 2019, 28, 805. doi: 10.1007/s00044-019-02310-y
[33]	Singh, I. P.; Gupta, S.; Kumar, S. Med. Chem. 2020, 16, 4. doi: 10.2174/1573406415666190614101253
[34]	Morcoss, M. M.; Abdelhafez, E. S. M. N.; Abdel-Rahman, H. M.; Abdel-Aziz, M.; El-Ella, D. A. A. J. Adv. Biomed. Pharm. Sci. 2020, 3, 45.
[35]	Özdemir, A.; Turanlý, S.; Çalýþkan, B.; Arka, M.; Banoglu, E. Pharm. Chem. J. 2020, 53, 1036.
[36]	Tokuhara, H.; Imaeda, Y.; Fukase, Y.; Iwanaga, K.; Taya, N.; Watanabe, K.; Kanagawa, R.; Matsuda, K.; Kajimoto, Y.; Kusumoto, K.; Kondo, M.; Snell, G.; Behnke, C. A.; Kuroita, T. Bioorg. Med. Chem. 2018, 26, 3261.
[37]	Adegboye, A. A.; Khan, K. M.; Salar, U.; Aboaba, S. A.; Kanwal, Chigurupati, S.; Fatima, I.; Taha, M.; Wadood, A.; Mohammad, J. I.; Khan, H.; Perveen, S. Eur. J. Med. Chem. 2018, 150, 248.
[38]	Brown, A. D.; Bagal, S. K.; Blackwell, P.; Blakemore, D. C.; Brown, B.; Bungay, P. J.; Corless, M.; Crawforth, J.; Fengas, D.; Fenwick, D. R.; Gray, V.; Kemp, M.; Klute, W.; Sanz, L. M.; Miller, D.; Murata, Y.; Payne, C. E.; Skerratt, S.; Stevens, E. B.; Warmus, J. S. Bioorg. Med. Chem. 2019, 27, 230. doi: 10.1016/j.bmc.2018.12.002
[39]	Antoci, V.; Cucu, D.; Zbancioc, G.; Moldoveanu, C.; Mangalagiu, V.; Amariucai-Mantu, D.; Aricu, A.; Mangalagiu, I. I. Future Med. Chem. 2020, 12, 207. doi: 10.4155/fmc-2019-0063
[40]	Zhang, T. R.; Liu, Q. Q.; Ren, Y. J. Tetrahedron 2020, 76, 131027. doi: 10.1016/j.tet.2020.131027
[41]	Spasov, A. A.; Zhukovskaya, O. N.; Maltsev, D. V.; Miroshnikov, M. V.; Skripka, M. O.; Sultanova, K. T.; Morkovnik, A. S. Russ. J. Bioorg. Chem. 2020, 46, 107.
[42]	Rahim, F.; Ullah, K.; Ullah, H.; Wadood, A.; Taha, M.; Rehman, A. U.; Uddin, I.; Ashraf, M.; Shaukat, A.; Rehman, W.; Hussain, S.; Khan, K. M. Bioorg. Chem. 2015, 58, 81. doi: 10.1016/j.bioorg.2014.12.001
[43]	Zhan, J. Y.; Ma, K.; Zheng, Q. C.; Yang, G. H.; Zhang, H. X. J. Biomol. Struct. Dyn. 2019, 37, 1724.
[44]	Rahima, F.; Tariq, S.; Taha, M.; Ullah, H.; Zaman, K.; Uddin, I.; Wadood, A.; Khan, A. A.; Rehman, A. U.; Uddin, N.; Zafar, S.; Shah, S. A. A. Bioorg. Chem. 2019, 92, 103284. doi: 10.1016/j.bioorg.2019.103284
[45]	Zhang, Q.; Ding, D. R.; Zeng, S. X.; Ye, Q. Z.; Lu, H. PloS One 2012, 7, e46294. doi: 10.1371/journal.pone.0046294
[46]	Ali, R. S.; Saad, H. A. Molecules 2018, 23, 693. doi: 10.3390/molecules23030693
[47]	Sivendran, S.; Jones, V.; Sun, D. Q.; Wang, Y.; Grzegorzewicz, A. E.; Scherman, M. S.; Napper, A. D.; McCammon, J. A.; Lee, R. E.; Diamond, S. L.; McNeil, M. Bioorg. Med. Chem. 2010, 18, 896. doi: 10.1016/j.bmc.2009.11.033
[48]	Upadhyay, K.; Manvar, A.; Loddo, R.; Colla, P. L.; Virsodiya, V.; Trivedi, J.; Chaniyara, R.; Shah, A. Med. Chem. Res. 2013, 22, 3675.
[49]	Li, Y. J.; Wang, S. Y.; Jin, K.; Gao, L. X.; Sheng, L.; Zhang, N.; Liu, J.-H.; Li, J. Chin. J. Org. Chem. 2019, 39, 491. (in Chinese).
	( 李英俊, 王思远, 靳焜, 高立信, 盛丽, 张楠, 刘继红, 李佳, 有机化学, 2019, 39, 491.)
[50]	Li, Y. J.; Liu, X. J.; Liu, J. H.; Gao, L. X.; Jin, K.; Sheng, L.; Yang, H. J.; Lin, L. D.; Li, J. Chin. J. Org. Chem. 2020, 40, 478. (in Chinese).
	( 李英俊, 刘雪洁, 刘季红, 高立信, 靳焜, 盛丽, 杨鸿境, 林乐弟, 李佳, 有机化学, 2020, 40, 478.)
[51]	Li, Y. J.; Zhao, Y.; Jin, K.; Gao, L. X.; Sheng, L.; Liu, X. J.; Yang, H. J.; Lin, L. D.; Li, J. Chin. J. Org. Chem. 2019, 39, 2599. (in Chinese).
	( 李英俊, 赵月, 靳焜, 高立信, 盛丽, 刘雪洁, 杨鸿境, 林乐弟, 李佳, 有机化学, 2019, 39, 2599.)
[52]	Hidrazitler, A. K.; Karakterizasyonu, S. Hacettepe J. Biol. Chem. 2018, 46, 169.
[53]	Ning, Y.-C. Structural Identification of Organic Compounds and Organic Spectroscopy, 2nd ed., Science Press, Beijing, 2000, p. 53. (in Chinese).
	( 宁永成, 有机化合物结构鉴定与有机波谱学, 第2版, 科学出版社, 北京, 2000, p. 53.)
[54]	Li, Y. J.; Zhang, N.; Jin, K.; Xu, Y. T.; Wang, S. Y.; Zhou, X. X. Chin. J. Org. Chem. 2017, 37, 2640. (in Chinese).
	( 李英俊, 张楠, 靳焜, 许永廷, 王思远, 周晓霞, 有机化学, 2017, 37, 2640.)
[55]	Li, Y. J.; Liu, L. J.; Jin, K.; Sun, S. Q.; Xu, Y. T. Acta Chim. Sinica 2010, 68, 1577. (in Chinese).
	( 李英俊, 刘丽军, 靳焜, 孙淑琴, 许永廷, 化学学报, 2010, 68, 1577.)
[56]	Li, Y. J.; Yang, H. J.; Jin, K.; Lin, L. D.; Liu, X. J. Chin. J. Magn. Reson. 2020, 37, 496. (in Chinese).
	李英俊, 杨鸿境, 靳焜, 林乐弟, 刘雪洁, 波谱学杂志, 2020, 37, 496. (in Chinese).
[57]	Li, Y. J.; Li, J. Y.; Xu, Y. T.; Jin, K.; Cao, X. Chin. J. Org. Chem. 2017, 37, 896. (in Chinese).
	( 李英俊, 李继阳, 许永廷, 靳焜, 曹欣, 有机化学, 2017, 37, 896.)
[58]	Grigoras, M.; Antonoaia, N.-C. Eur. Polym. J. 2005, 41, 1079. doi: 10.1016/j.eurpolymj.2004.11.019
[59]	Sun, L. P.; Shen, Q.; Piao, H. H.; Ma, W. P.; Gao, L. X.; Zhang, W.; Nan, F. J.; Li, J.; Piao, H. R. Eur. J. Med. Chem. 2011, 46, 3630.

Position	δ_H		¹H-¹H COSY A (B)	NOESY A (B)
Position	A	B	¹H-¹H COSY A (B)	NOESY A (B)
1 (1')	7.86 (d, J=8.5 Hz)	—^a	H-2 (—)	/
2 (2')	7.93 (dd, J=8.8, 1.3 Hz)	7.86	H-1, 4	H-9/H-9'
3 (3')	/^b	/	/	/
4 (4')	8.50 (d, J=1.0 Hz)	8.47	H-2 (H-2')	/
5 (5')	8.24 (d, J=8.0 Hz)	8.23 (d, J=8.0 Hz)	H-6 (—)	/
6 (6')	7.29 (t, J=7.5 Hz)	—	H-5, 7 (—)	/
7 (7')	7.53 (td, J=7.8, 1.0 Hz)	—	H-6, 8 (—)	/
8 (8')	7.83 (d, J=8.5 Hz)	—	H-7 (—)	H-13 (—)
9 (9')	8.20	8.37	/	H-2/H-2'/H-10/H-10'
10 (10')	11.74	11.80	/	H-9/H-9'/H-11/H-11'
11 (11')	5.68	5.17	/	H-10/H-10'/H-15 (—)
12 (12')	5.44	—	/	H-19 (—)
13 (13')	5.95	5.94	/	H-8 (—)/H-14 (—)
14 (14')	7.88	—	/	H-13 (—)
15 (15')	7.614 (d, J=7.5 Hz)	7.606 (d, J=7.5 Hz)	H-16 (—)	H-11 (—)
16 (16')	7.27 (t, J=7.0 Hz)	—	H-15, 17 (—)	/
17 (17')	7.24 (td, J=7.5, 1.0 Hz)	—	H-16, 18 (—)	/
18 (18')	7.69 (d, J=7.5 Hz)	—	H-17 (—)	/
19 (19')	7.10 (d, J=9.5 Hz)	—	H-20 (—)	H-12 (—)
20 (20')	7.26 (d, J=9.0 Hz)	—	H-19 (—)	/

Position	δ_H		¹H-¹H COSY A (B)	NOESY A (B)
Position	A	B	¹H-¹H COSY A (B)	NOESY A (B)
1 (1')	7.86 (d, J=8.5 Hz)	—^a	H-2 (—)	/
2 (2')	7.93 (dd, J=8.8, 1.3 Hz)	7.86	H-1, 4	H-9/H-9'
3 (3')	/^b	/	/	/
4 (4')	8.50 (d, J=1.0 Hz)	8.47	H-2 (H-2')	/
5 (5')	8.24 (d, J=8.0 Hz)	8.23 (d, J=8.0 Hz)	H-6 (—)	/
6 (6')	7.29 (t, J=7.5 Hz)	—	H-5, 7 (—)	/
7 (7')	7.53 (td, J=7.8, 1.0 Hz)	—	H-6, 8 (—)	/
8 (8')	7.83 (d, J=8.5 Hz)	—	H-7 (—)	H-13 (—)
9 (9')	8.20	8.37	/	H-2/H-2'/H-10/H-10'
10 (10')	11.74	11.80	/	H-9/H-9'/H-11/H-11'
11 (11')	5.68	5.17	/	H-10/H-10'/H-15 (—)
12 (12')	5.44	—	/	H-19 (—)
13 (13')	5.95	5.94	/	H-8 (—)/H-14 (—)
14 (14')	7.88	—	/	H-13 (—)
15 (15')	7.614 (d, J=7.5 Hz)	7.606 (d, J=7.5 Hz)	H-16 (—)	H-11 (—)
16 (16')	7.27 (t, J=7.0 Hz)	—	H-15, 17 (—)	/
17 (17')	7.24 (td, J=7.5, 1.0 Hz)	—	H-16, 18 (—)	/
18 (18')	7.69 (d, J=7.5 Hz)	—	H-17 (—)	/
19 (19')	7.10 (d, J=9.5 Hz)	—	H-20 (—)	H-12 (—)
20 (20')	7.26 (d, J=9.0 Hz)	—	H-19 (—)	/

Compd.	Ar/Ar'	IC₅₀/(μmol•L^–1)	Compd.	Ar/Ar'	IC₅₀/(μmol•L^–1)
6a	C₆H₅	6.14±0.00	7a	4-CH₃C₆H₄	1.91±0.32
6b	4-CH₃C₆H₄	3.05±0.96	7b	2,4-(CH₃)₂C₆H₃	2.40±0.17
6c	4-CH₃OC₆H₄	2.26±0.32	7c	4-CH₃OC₆H₄	2.46±0.27
6d	4-BrC₆H₄	2.01±0.16	7d	4-ClC₆H₄	1.92±0.47
6e	3-ClC₆H₄	2.44±0.35	7e	3-O₂NC₆H₄	2.35±0.25
6f	4-ClC₆H₄	2.91±0.67	7f	1-C₁₀H₇	1.83±0.11
6g	3-O₂NC₆H₄	3.53±0.21	8		2.71±0.60
6h	4-O₂NC₆H₄	3.29±0.39	11a	3-O₂NC₆H₄	0.98±0.00
OA		2.93±0.92	11b	4-O₂NC₆H₄	0.89±0.06

Compd.	Ar/Ar'	IC₅₀/(μmol•L^–1)	Compd.	Ar/Ar'	IC₅₀/(μmol•L^–1)
6a	C₆H₅	6.14±0.00	7a	4-CH₃C₆H₄	1.91±0.32
6b	4-CH₃C₆H₄	3.05±0.96	7b	2,4-(CH₃)₂C₆H₃	2.40±0.17
6c	4-CH₃OC₆H₄	2.26±0.32	7c	4-CH₃OC₆H₄	2.46±0.27
6d	4-BrC₆H₄	2.01±0.16	7d	4-ClC₆H₄	1.92±0.47
6e	3-ClC₆H₄	2.44±0.35	7e	3-O₂NC₆H₄	2.35±0.25
6f	4-ClC₆H₄	2.91±0.67	7f	1-C₁₀H₇	1.83±0.11
6g	3-O₂NC₆H₄	3.53±0.21	8		2.71±0.60
6h	4-O₂NC₆H₄	3.29±0.39	11a	3-O₂NC₆H₄	0.98±0.00
OA		2.93±0.92	11b	4-O₂NC₆H₄	0.89±0.06

新型含咔唑环和芳环/芳稠杂环的N-酰腙衍生物的合成及蛋白酪氨酸磷酸酶1B (PTP1B)抑制活性评价

Synthesis and Protein Tyrosine Phosphatase 1B (PTP1B) Inhibitory Activity Evaluation of Novel N-Acylhydrazone Derivatives Containing Carbazole and Aromatic Ring/Aromatic Fused Heterocycle

RichHTML

PDF

Supporting Info.

Knowledge

Abstract

Cite this article

share this article

Fig. & Tab. 16

References 59

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Fakai Zou, Nengzhong Wang, Hui Yao, Hui Wang, Mingguo Liu, Nianyu Huang. Regio- and Stereo-selective Synthesis of 1β-/3R-Aryl Thiosugar [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 593-604.
[2]	Simin Wu, Jiaxin Tang, Yujia Zhou, Xuetao Xu, Haoxing Zhang, Shaohua Wang. α-Glucosidase Inhibition Research of Derivatives Based on 2β-Acetoxyferruginol Scaffold Excluding Acetic Acid Group [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 613-621.
[3]	Luyao Li, Zhongwen He, Zhenguo Zhang, Zhenhua Jia, Teck-Peng Loh. Application of Triaryl Carbenium in Organic Synthesis [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 421-437.
[4]	Qinggang Mei, Qinghan Li. Recent Progress of Visible Light-Induced the Synthesis of C(3) (Hetero)arylthio Indole Compounds [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 398-408.
[5]	Penghui Li, Qingyang Xie, Fuxian Wan, Yuanhong Zhang, Lin Jiang. Synthesis and Fungicidal Activity of Novel Substituted Pyrimidine-5-carboxamides Bearing Cyclopropyl Moiety [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 650-656.
[6]	Weiqing Yang, Yanbing Ge, Yuanyuan Chen, Ping Liu, Haiyan Fu, Menglin Ma. Design and Synthesis of Fluorescent 1,8-Napthalimide Derivatives and Their Identification of Cysteine [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 180-194.
[7]	Qianfan Zhao, Yongzheng Chen, Shiming Zhang. Application and Mechanism Study of Carbon-Based Metal-Free Catalysts in Organic Synthesis [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 137-147.
[8]	Shan Chen, Zhilin Chen, Qiong Hu, Yanshuang Meng, Yue Huang, Pingfang Tao, Liru Lu, Guobao Huang. Recognition of Bis-thiourea Tweezers to Neutral Molecules in Non-Polar Solvent [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 277-281.
[9]	Huakun Wang, Xiaolong Ren, Yining Xuan. Study of the Halide Salt Catalyzed [3＋2] Cycloaddition of α,β-Epoxy Carboxylate with Isocyanate [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 251-258.
[10]	Yukun Jin, Baoyi Ren, Fushun Liang. Visible Light-Mediated Selective C—F Bond Cleavage of Trifluoromethyl Groups and Its Application in Synthesizing gem-Difluoro-Containing Compounds [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 85-110.
[11]	Cuiyun Ma, Hailan Luo, Fuhua Zhang, Dan Guo, Shuxing Chen, Fei Wang. Green Biosynthesis, Photophysical Properties and Application of 3-Pyrrolyl BODIPY [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 216-223.
[12]	Bozhen Wang, Jie Zhang, Chunhui Nian, Mingming Jin, Miaomiao Kong, Wulan Li, Wenfei He, Jianzhang Wu. Synthesis and Antitumor Activity of 3,4-Dichlorophenyl Amides [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 232-241.
[13]	Shihang Yu, Jiawei Liu, Biyu An, Qinghua Bian, Min Wang, Jiangchun Zhong. Asymmetric Synthesis of the Contact Sex Pheromone of Neoclytus acuminatus acuminatus (Fabricius) [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 301-308.
[14]	Yang Li, Jinding Yuan, Di Zhao. Deep Eutectic Solvent of 1,3-Dimethylurea/L-(+)-Tartaric Acid for the Green Synthesis of (E)-2-Styrylquinoline-3-carboxylic Acid Derivatives [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3268-3276.
[15]	Dandan Sui, Nannan Cen, Ruoqu Gong, Yang Chen, Wenbo Chen. Supporting-Electrolyte-Free Electrochemical Synthesis of Trifluoromethylated Oxindoles in Continuous Flow [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3239-3245.