新型含咔唑环芳氨基乙酰腙衍生物的合成及其蛋白酪氨酸磷酸酶1B (PTP1B)抑制活性评价

doi:10.6023/cjoc202102046

有机化学 ›› 2021, Vol. 41 ›› Issue (8): 3157-3170.DOI: 10.6023/cjoc202102046 上一篇下一篇

研究论文

新型含咔唑环芳氨基乙酰腙衍生物的合成及其蛋白酪氨酸磷酸酶1B (PTP1B)抑制活性评价

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

a 辽宁师范大学化学化工学院辽宁大连 116029
b 大连理工大学精细化工国家重点实验室辽宁大连 116012
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 大连理工大学化学分析测试中心辽宁大连 116023

收稿日期:2021-02-24 修回日期:2021-04-02 发布日期:2021-05-14
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 Arylaminoacetylhydrazone Derivatives Containing Carbazole Moiety

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

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

Received:2021-02-24 Revised:2021-04-02 Published:2021-05-14
Contact: Yingjun Li, Jia Li
Supported by:
Natural Science Foundation of Liaoning Province(20102126)

文章分享

1. 213157S.pdf(4455KB)

摘要/Abstract

为寻找新型蛋白酪氨酸磷酸酶1B (PTP1B)抑制剂, 设计并合成了一系列新型含咔唑环芳氨基乙酰腙衍生物. 其结构和构型用IR、¹H NMR、¹³C NMR和2D NMR(包括¹H-¹H COSY、¹H-¹³C HMBC和NOESY)谱及元素分析进行了确证. 通过对PTP1B抑制活性的测试发现, 目标化合物对PTP1B有较强的抑制作用, 且大多数化合物的IC₅₀值低于阳性对照药物齐墩果酸, 其中N'-(9-辛基咔唑-3-亚甲基)-2-(4-硝基苯氨基)乙酰肼(3t)活性最高, IC₅₀=(2.78±0.04) μmol/L. 利用分子对接研究了化合物3t与PTP1B酶的结合情况.

关键词: 蛋白酪氨酸磷酸酶1B (PTP1B)抑制剂, 咔唑, 芳氨基乙酰腙, 合成, 分子对接

In order to find novel protein tyrosine phosphatase 1B (PTP1B) inhibitors, a series of novel arylaminoacetylhydrazone derivatives containing carbazole moiety were designed and synthesized. Their structures and configurations were confirmed by IR, ¹H NMR, ¹³C NMR, two-dimensional NMR spectra (including ¹H-¹H COSY, ¹H-¹³C HMBC and NOESY) and elemental analysis. The inhibitory activities of all the target compounds against PTP1B were tested, and it was found that the target compounds had potent inhibitory activity against PTP1B, and most of them had lower IC₅₀ value than the positive control drug oleanolic acid. Among them, N'-(9-octylcarbazol-3-ylmethylene)-2-(4-nitrophenylamino)acetohydrazide (3t) had the highest inhibitory activity against PTP1B with IC₅₀ of (2.78±0.04) μmol/L. Molecular docking was used to study the bind of compound 3t with PTP1B enzyme.

Key words: protein tyrosine phosphatase 1B (PTP1B) inhibitor, carbazole, arylaminoacetylhydrazone, synthesis, molecular docking

引用此文

李英俊, 林乐弟, 靳焜, 高立信, 盛丽, 刘季红, 李佳. 新型含咔唑环芳氨基乙酰腙衍生物的合成及其蛋白酪氨酸磷酸酶1B (PTP1B)抑制活性评价[J]. 有机化学, 2021, 41(8): 3157-3170.

Yingjun Li, Ledi Lin, Kun Jin, Lixin Gao, Li Sheng, Jihong Liu, Jia Li. Synthesis and Protein Tyrosine Phosphatase 1B (PTP1B) Inhibitory Activity Evaluation of Novel Arylaminoacetylhydrazone Derivatives Containing Carbazole Moiety[J]. Chinese Journal of Organic Chemistry, 2021, 41(8): 3157-3170.

导出引用 EndNote|Reference Manager|ProCite|BibTeX|RefWorks

分享此文

图/表 12

参考文献 45

[1]	Eleftheriou, P.; Geronikaki, A.; Petrou, A. Curr. Top. Med. Chem. 2019, 19, 246. doi: 10.2174/1568026619666190201152153 pmid: 30714526
[2]	Kostrzewa, T.; Styszko, J.; Gorska-Ponikowska, M.; Sledzinski, T.; Kuban-Jankowska, A. Anticancer Res. 2019, 39, 3379. doi: 10.21873/anticanres.13481 pmid: 31262859
[3]	Kuban-Jankowska, A.; Gorska-Ponikowska, M.; Wozniak, M. Anticancer Res. 2017, 37, 2893. pmid: 28551626
[4]	Gulipalli, K. C.; Bodige, S.; Ravula, P.; Endoori, S.; G. R. V.; Babu, G. S.; Chandra, J. N. N. S.; Seelam, N. Bioorg. Med. Chem. Lett. 2017, 27, 3558. doi: S0960-894X(17)30528-0 pmid: 28579122
[5]	Lessard, L.; Labbé, D. P.; Deblois, G.; Bégin, L. R.; Hardy, S.; Mes-Masson, A-M.; Saad, F.; Trotman, L. C.; Giguère, V.; Tremblay, M. L. Cancer Res. 2012, 72, 1529. doi: 10.1158/0008-5472.CAN-11-2602
[6]	Kostrzewa, T.; Przychodzen, P.; Gorska-Ponikowska, M.; Kuban-Jankowska, A. Anticancer Res. 2019, 39, 745. doi: 10.21873/anticanres.13171 pmid: 30711953
[7]	Hussain, H.; Green, I. R.; Abbas, G.; Adekenov, S. M.; Hussain, W.; Ali, I. Expert Opin. Ther. Pat. 2019, 29, 689. doi: 10.1080/13543776.2019.1655542
[8]	Guo, S. J.; Wang, L.J, Chen, D.; Jiang, B. RSC Adv. 2020, 10, 3429. doi: 10.1039/C9RA10660J
[9]	Kim, D. H.; Lee, S.; Chung, Y. W.; Kim, B. M.; Kim, H.; Kim, K.; Yang, K. M. Biomed. Res. Int. 2016, 2016, 8432759.
[10]	Krishnan, N.; Konidaris, K. F.; Gasser, G.; Tonks, N. K. J. Biol. Chem. 2018, 293, 1517. doi: 10.1074/jbc.C117.819110
[11]	Abdelsalam, S. S.; Korashy, H. M.; Zeidan, A.; Agouni, A. Biomolecules 2019, 9, 286. doi: 10.3390/biom9070286
[12]	Kumar, A.; Rana, D.; Rana, R.; Bhatia, R. Curr. Mol. Pharm. 2020, 13, 17. doi: 10.2174/1874467212666190724150723
[13]	Dodd, G. T.; Xirouchaki, C. E.; Eramo, M.; Mitchell, C. A.; Andrews, Z. B.; Henry, B. A.; Cowley, M. A.; Tiganis, T. Cell Rep. 2019, 28, 2905. doi: 10.1016/j.celrep.2019.08.019
[14]	Liu, H. Y.; Sun, D. W.; Du, H.; Zheng, C. J.; Li, J. Y.; Piao, H. R.; Li, J.; Sun, L. P. Eur. J. Med. Chem. 2019, 172, 163. doi: 10.1016/j.ejmech.2019.03.059
[15]	Sharma, B.; Xie, L. X.; Yang, F.; Wang, W.; Zhou, Q. M.; Xiang, M. H.; Zhou, S. Z.; Lv, W. T.; Jia, Y.; Pokhrel, L.; Shen, J.; Xiao, Q. C.; Gao, L. Q.; Deng, W. B. Eur. J. Med. Chem. 2020, 199, 112376. doi: 10.1016/j.ejmech.2020.112376
[16]	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) doi: 10.6023/cjoc201907043
	(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.) doi: 10.6023/cjoc201907043
[17]	Li, Y.-J.; Yang, H.-J.; Cao, X.; Gao, L.-X.; Jin, K.; Sheng, L.; Liu, J.-H.; Liu, X.-J.; Li, J. Chin. J. Appl. Chem. 2020, 37, 994. (in Chinese)
	(李英俊, 杨鸿境, 曹欣, 高立信, 靳焜, 盛丽, 刘继红, 刘雪洁, 李佳, 应用化学, 2020, 37, 994.)
[18]	Alotabi, S. H. Arabian J. Chem. 2020, 13, 4771. doi: 10.1016/j.arabjc.2019.12.006
[19]	Hamoud, M. M. S.; Ghanim, A, M.; Osman, N. A.; Hassan, A. E. A.; Abdel-Fattah, H. A.; Sebaiy, M. M. Med. Analy. Chem. Int. J. 2020, 4, 000159.
[20]	Liu, K.; Ding, Y. Y.; Kang, C. M. Pharm. Chem. J. 2020, 54, 345. doi: 10.1007/s11094-020-02215-w
[21]	Aarjane, M.; Aouidate, A.; Slassi, S.; Amine, A. Arabian J. Chem. 2020, 13, 6236. doi: 10.1016/j.arabjc.2020.05.034
[22]	Sinha, R.; Singh, U. V. S.; Khosa, R. L.; Jain, J. J. Appl. Pharm. Sci. Res. 2018, 1, 16.
[23]	Costa, G. C.; Montagnoli, T. L.; Soares Da Silva, J.; Nogueira de Alencar, A. K.; Gamba, L. E. R.; Alves, B. E. O.; Carvalho da Silva, M. M.; Trachez, M. M.; M do Nascimento, J. H.; 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
[24]	Cordeiro, N. de, M.; Freitas, R. H. C. N.; Fraga, C. A. M.; Fernandes, P. D. J. Pharmacol. Exp. Ther. 2020, 374, 420. doi: 10.1124/jpet.120.000074 pmid: 32546529
[25]	Balakrishnan, R.; Vijayraja, D.; Jo, S.-H.; Ganesan, P.; Su-Kim, I.; Choi, D.-K. Antioxid 2020, 9, 101. doi: 10.3390/antiox9020101
[26]	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
[27]	Wang, W. B.; Zhou, Z. G.; Zhou, X. H.; Chen, L. M.; Bie, S.; Jing, Z. J. AMB Express 2020, 10, 148. doi: 10.1186/s13568-020-01074-8
[28]	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
[29]	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
[30]	Sadeghian, B.; Sakhteman, A.; Faghih, Z.; Nadri, H.; Edraki, N.; Iraji, A.; Sadeghian, I.; Rezaei, Z. J. Mol. Struct. 2020, 1221, 128793. doi: 10.1016/j.molstruc.2020.128793
[31]	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
[32]	Aminah, N. S.; Thant, T. M.; Kristanti, A. N.; Ramadhan, R.; Aung, H. T.; Takaya, Y. Nat. Prod. Commun. 2020, 14, 1.
[33]	Sullivan, H.-J.; Wang, X. Y.; Nogle, S.; Liao, S.; Wu, C. PPAR Res. 2020, 2020, 5314187.
[34]	Sutkuvienė, S.; Sakalauskaitė, S.; Kuliešienė, N.; Ragelienė, L.; Daugelavičius, R. Biologija 2020, 66, 80.
[35]	Mehta, S.; Kumar, S.; Marwaha, R. K.; Narasimhan, B.; Ramasamy, K.; Lim, S. M.; Shah, S. A. A.; Mani, V. BMC Chem. 2019, 13, 113. doi: 10.1186/s13065-019-0629-0
[36]	Kerur, S.; Alagawadi, K.; Zhu, H.-L.; Manvi, F. Indian J. Pharm. Educ. Res. 2016, 50, 465. doi: 10.5530/ijper
[37]	Aly, S. A. J. Radiat. Res. Appl. Sci. 2017, 11, 163.
[38]	Ren, W. X.; Ren, Y. J.; Wang, S. Eur. J. Med. Chem. 2016, 120, 148. doi: 10.1016/j.ejmech.2016.05.020
[39]	Abdel-Aal, M. T.; El-Sayed, W. A.; El-Ashry, E.-S. H. Arch. Pharm. Chem. Life Sci. 2006, 339, 656. doi: 10.1002/(ISSN)1521-4184
[40]	Abdel-Aal, M. T.; El-Sayed, W. A.; El-Kosy, S. M.; El-Ashry, E. S. H. Arch. Pharm. Chem. Life Sci. 2008, 341, 307. doi: 10.1002/(ISSN)1521-4184
[41]	El-Sayed, W. A.; Fathi, N. M.; Gad, W. A.; El-Ashry, E. S. H. J. Carbohydr. Chem. 2008, 27, 357. doi: 10.1080/07328300802262778
[42]	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) doi: 10.6023/cjoc201806042
	(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.) doi: 10.6023/cjoc201806042
[43]	Ning, Y.-C. Structural Identification of Organic Compounds and Organic Spectroscopy, 2 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, 科学出版社, 北京, 2000, p. 53.)
[44]	Li, Y.-J.; Zhang, Y.-X.; Xu, Y.-T.; Sun, S.-Q.; Wang, Y.; Liu, S.-N. Chin. J. Org. Chem. 2003, 23, 1442. (in Chinese)
	(李英俊, 张颖新, 许永廷, 孙淑琴, 王营, 刘素娜, 有机化学, 2003, 23, 1442.)
[45]	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. doi: 10.1016/j.ejmech.2011.05.027

Position	δ_H	¹H-¹H COSY A (B)	NOESY A (B)
Position	A	B	NOESY A (B)
1 (1')	7.65 (d, J=8.5 Hz)	—	H-2 (—)	H-16 (—)
2 (2')	7.92 (dd, J=8.5, 1.0 Hz)	7.87 (dd, J=8.5, 1.0 Hz)	H-1,4 (H-4')	H-9/H-9'
3 (3')	/	/	/	/
4 (4')	8.48	8.46	H-2 (—)	/
5 (5')	8.25 (d, J=7.5 Hz)	8.21 (d, J=7.5 Hz)	H-6 (H-6')	/
6 (6')	7.244 (t, J=7.5 Hz)	7.237 (t, J=7.5 Hz)	H-5,7 (H-5')	/
7 (7')	7.48 (t, J=7.0 Hz)	—	H-6,8 (—)	/
8 (8')	7.61 (d, J=8.0 Hz)	—	H-7 (—)	H-16 (—)
9 (9')	8.22	8.41	/	H-2/H-2'/H-10/H-10'
10 (10')	11.59	11.56	/	H-9/H-9'/–/H-12'
11 (11')	/	/	/	/
12 (12')	4.51 (d, J=6.0 Hz)	4.04 (d, J=6.0 Hz)	H-13 (—)	(—)/H-10'/H-14/H-14'
13 (13')	7.47	—	H-12 (—)	H-14 (—)
14 (14')	6.79 (d, J=9.0 Hz)	6.74 (d, J=9.0 Hz)	H-15 (H-15')	H-12/H-12'/H-13
15 (15')	8.04 (d, J=9.0 Hz)	8.06 (d, J=9.0 Hz)	H-14 (H-14')	/
16 (16')	4.40 (t, J=6.5 Hz)	4.38 (t, J=6.5 Hz)	/	H-1/H-8

Position	δ_H	¹H-¹H COSY A (B)	NOESY A (B)
Position	A	B	NOESY A (B)
1 (1')	7.65 (d, J=8.5 Hz)	—	H-2 (—)	H-16 (—)
2 (2')	7.92 (dd, J=8.5, 1.0 Hz)	7.87 (dd, J=8.5, 1.0 Hz)	H-1,4 (H-4')	H-9/H-9'
3 (3')	/	/	/	/
4 (4')	8.48	8.46	H-2 (—)	/
5 (5')	8.25 (d, J=7.5 Hz)	8.21 (d, J=7.5 Hz)	H-6 (H-6')	/
6 (6')	7.244 (t, J=7.5 Hz)	7.237 (t, J=7.5 Hz)	H-5,7 (H-5')	/
7 (7')	7.48 (t, J=7.0 Hz)	—	H-6,8 (—)	/
8 (8')	7.61 (d, J=8.0 Hz)	—	H-7 (—)	H-16 (—)
9 (9')	8.22	8.41	/	H-2/H-2'/H-10/H-10'
10 (10')	11.59	11.56	/	H-9/H-9'/–/H-12'
11 (11')	/	/	/	/
12 (12')	4.51 (d, J=6.0 Hz)	4.04 (d, J=6.0 Hz)	H-13 (—)	(—)/H-10'/H-14/H-14'
13 (13')	7.47	—	H-12 (—)	H-14 (—)
14 (14')	6.79 (d, J=9.0 Hz)	6.74 (d, J=9.0 Hz)	H-15 (H-15')	H-12/H-12'/H-13
15 (15')	8.04 (d, J=9.0 Hz)	8.06 (d, J=9.0 Hz)	H-14 (H-14')	/
16 (16')	4.40 (t, J=6.5 Hz)	4.38 (t, J=6.5 Hz)	/	H-1/H-8

Compd.	X	R	PTP1B^a
Compd.	X	R	Inhibition/% at 20 μg/mL	IC₅₀/(μmol•L^–1)
3a	4-OCH₃	C₂H₅	93.19±1.27	9.91±1.72
3b	4-OCH₃	n-C₃H₇	93.92±1.48	9.00±0.63
3c	4-OCH₃	n-C₄H₉	91.82±0.32	9.31±0.16
3d	4-OCH₃	n-C₅H₁₁	81.15±2.86	7.68±1.56
3e	4-OCH₃	n-C₆H₁₃	76.38±10.73	5.26±1.66
3f	4-OCH₃	n-C₇H₁₅	74.15±1.24	5.38±2.74
3g	4-OCH₃	n-C₈H₁₇	53.68±0.33	7.76±0.54
3h	3-Cl	C₂H₅	90.21±1.19	7.09±1.11
3i	3-Cl	n-C₃H₇	95.32±0.16	5.80±0.72
3j	3-Cl	n-C₄H₉	95.24±0.15	3.88±0.02
3k	3-Cl	n-C₅H₁₁	96.46±0.24	6.67±0.18
3l	3-Cl	n-C₆H₁₃	96.03±1.67	4.14±0.13
3m	3-Cl	n-C₇H₁₅	93.34±0.21	4.51±0.23
3n	3-Cl	n-C₈H₁₇	83.08±3.72	5.48±2.58
3o	4-NO₂	n-C₃H₇	77.04±1.71	5.59±0.98
3p	4-NO₂	n-C₄H₉	74.05±2.13	4.08±1.38
3q	4-NO₂	n-C₅H₁₁	73.23±0.85	5.57±1.33
3r	4-NO₂	n-C₆H₁₃	95.37±1.33	4.41±1.17
3s	4-NO₂	n-C₇H₁₅	96.39±0.24	3.27±0.47
3t	4-NO₂	n-C₈H₁₇	96.70±1.63	2.78±0.04

Compd.	X	R	PTP1B^a
Compd.	X	R	Inhibition/% at 20 μg/mL	IC₅₀/(μmol•L^–1)
3a	4-OCH₃	C₂H₅	93.19±1.27	9.91±1.72
3b	4-OCH₃	n-C₃H₇	93.92±1.48	9.00±0.63
3c	4-OCH₃	n-C₄H₉	91.82±0.32	9.31±0.16
3d	4-OCH₃	n-C₅H₁₁	81.15±2.86	7.68±1.56
3e	4-OCH₃	n-C₆H₁₃	76.38±10.73	5.26±1.66
3f	4-OCH₃	n-C₇H₁₅	74.15±1.24	5.38±2.74
3g	4-OCH₃	n-C₈H₁₇	53.68±0.33	7.76±0.54
3h	3-Cl	C₂H₅	90.21±1.19	7.09±1.11
3i	3-Cl	n-C₃H₇	95.32±0.16	5.80±0.72
3j	3-Cl	n-C₄H₉	95.24±0.15	3.88±0.02
3k	3-Cl	n-C₅H₁₁	96.46±0.24	6.67±0.18
3l	3-Cl	n-C₆H₁₃	96.03±1.67	4.14±0.13
3m	3-Cl	n-C₇H₁₅	93.34±0.21	4.51±0.23
3n	3-Cl	n-C₈H₁₇	83.08±3.72	5.48±2.58
3o	4-NO₂	n-C₃H₇	77.04±1.71	5.59±0.98
3p	4-NO₂	n-C₄H₉	74.05±2.13	4.08±1.38
3q	4-NO₂	n-C₅H₁₁	73.23±0.85	5.57±1.33
3r	4-NO₂	n-C₆H₁₃	95.37±1.33	4.41±1.17
3s	4-NO₂	n-C₇H₁₅	96.39±0.24	3.27±0.47
3t	4-NO₂	n-C₈H₁₇	96.70±1.63	2.78±0.04

Est. free energy/ (kJ/mol) of binding	No. of H-bond	H-bond (length/nm)	Polar (length/nm)	Hydrophobic (length/nm)	π-π (length/nm)
–25.75	5	N(2)-VAL184 (0.349)	H(26)-GLU186 (0.245)	C(9)-PRO180 (0.352)	C(4)-TYR152 (0.382)
		N(3)-VAL184 (0.300)	O(2)-ARG268 (0.370)	C(10)-PRO180 (0.314)
		N(4)-VAL184 (0.306)	O(3)-ARG268 (0.336)	C(11)-PRO180 (0.355)
		N(2)-GLU186 (0.265)	N(5)-ARG268 (0.387)	C(21)-PRO180 (0.324)
		N(3)-GLU186 (0.267)

新型含咔唑环芳氨基乙酰腙衍生物的合成及其蛋白酪氨酸磷酸酶1B (PTP1B)抑制活性评价

Synthesis and Protein Tyrosine Phosphatase 1B (PTP1B) Inhibitory Activity Evaluation of Novel Arylaminoacetylhydrazone Derivatives Containing Carbazole Moiety

RichHTML

PDF

补充材料

可视化

摘要/Abstract

引用此文

分享此文

图/表 12

参考文献 45

相关文章 15

编辑推荐

相关统计

本文评价

[1]	王娜娜, 徐敬成, 梅海波, Hiroki Moriwaki, Kunisuke Izawa, Vadim A. Soloshonok, 韩建林. 电化学合成氨基酸类化合物的研究进展[J]. 有机化学, 2021, 41(8): 3034-3049.
[2]	马姣丽, 郭鹏虎, 李静, 廖新成, 程辉成. 含1,3,4-噻二唑和吡唑的酰胺衍生物的合成和抗肿瘤活性研究[J]. 有机化学, 2021, 41(8): 3214-3222.
[3]	陆棋, 叶飞霞, 孙晓彤, 翁建全, 余茜, 胡德玄. 新型拟天然芪类拓扑异构酶I抑制剂的设计与合成[J]. 有机化学, 2021, 41(8): 3321-3329.
[4]	赵军, 肖检, 王雅雯, 彭羽. 基于氧化[3+2]环加成反应合成二氢苯并呋喃类天然产物[J]. 有机化学, 2021, 41(8): 2933-2945.
[5]	何凤, 郭声鑫, 代阿丽, 张仁凤, 吴剑. 含三氟甲基吡啶结构的酰胺类衍生物的合成、表征及生物活性研究[J]. 有机化学, 2021, 41(8): 3303-3311.
[6]	李敏欣, 邹秋萍, 杜文绒, 高金春, 李艳平, 毛泽伟. Dorsmerunin A的全合成及其抗炎活性研究[J]. 有机化学, 2021, 41(8): 3292-3296.
[7]	李世杰, 聂秋玥, 季珍瑜, 华会明, 唐功利. 组合生物合成介导C-4羟基异构的新型四环素类化合物的发现[J]. 有机化学, 2021, 41(8): 3297-3302.
[8]	袁谷城, 边庆花, 王敏, 钟江春. 手性甲基脂肪烃类昆虫信息素的合成研究进展[J]. 有机化学, 2021, 41(7): 2571-2586.
[9]	于奇, 杨帅, 唐聪云, 彭林, 左之利, 汪亮亮. 基于分子内的仿生Diels-Alder反应构建Elansolid A1/A2的四氢茚烷核心结构[J]. 有机化学, 2021, 41(7): 2820-2830.
[10]	周进, 孙宏顺, 李玉龙, 蒋蕻, 郭成, 沈临江. 一种大环类双核非离子型磁共振对比剂的合成及弛豫性能[J]. 有机化学, 2021, 41(7): 2767-2773.
[11]	王金艳, 董黎颖, 刘雅妮, 陈西同, 马艳楠, 尹昊, 杜姗姗, 齐昀坤, 王克威. 蜈蚣毒素多肽RhTx的高效化学合成及复性折叠研究[J]. 有机化学, 2021, 41(7): 2800-2809.
[12]	肖检, 彭羽, 李卫东. 倍半萜生物碱Dendrobine的全合成研究进展[J]. 有机化学, 2021, 41(7): 2636-2649.
[13]	孟薇, 徐坤, 郭兵兵, 曾程初. 电化学条件下的Minisci反应研究进展[J]. 有机化学, 2021, 41(7): 2621-2635.
[14]	李远志, 朱孟倩, 徐亮. 生源启发下的喜树碱的简洁形式合成[J]. 有机化学, 2021, 41(7): 2885-2890.
[15]	邹晓亮, 徐森苗. 铱催化的(杂)芳烃远端区域选择性C—H硼化反应的最新进展[J]. 有机化学, 2021, 41(7): 2610-2620.