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

doi:10.6023/cjoc202102046

Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (8): 3157-3170.DOI: 10.6023/cjoc202102046 Previous Articles Next Articles

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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)

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Abstract

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

Cite this article

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.

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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

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