Design, Synthesis and Biological Activity Studies of 2-(1,3-Dioxoiso-indolin-2-yl)-N-phenethylacetamide and 2-(3,4-Dihydroisoquinolin-1-yl)isoindole-1,3-dione as Monoamine Oxidase (MAO) and Cholinesterase (ChE) Inhibitors

doi:10.6023/cjoc202311027

Chinese Journal of Organic Chemistry ›› 2024, Vol. 44 ›› Issue (6): 1907-1919.DOI: 10.6023/cjoc202311027 Previous Articles Next Articles

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2-(1,3-二氧代异吲哚啉-2-基)-N-苯乙酰胺和2-(3,4-二氢异喹啉-1-基)异吲哚-1,3-二酮类单胺氧化酶(MAO)和胆碱酯酶(ChE)抑制剂的设计、合成和生物活性研究

胡懿鸣^a,†, 许嘉宇^a,†, 汤敏^a, 刘雅雯^a, 关丽萍^a^,^*(), 金晴昊^b^,^*()

a 浙江海洋大学食品与药学学院浙江舟山 316022
b 浙江药科职业大学护理学院浙江宁波 315153

收稿日期:2023-11-24 修回日期:2024-01-22 发布日期:2024-03-12
作者简介:
^†共同第一作者
基金资助:
福建省药物新靶点研究重点实验室开放课题资助(FJ-YW-2023KF04); 国家级大学生创新创业训练计划(202310340048)

Design, Synthesis and Biological Activity Studies of 2-(1,3-Dioxoiso-indolin-2-yl)-N-phenethylacetamide and 2-(3,4-Dihydroisoquinolin-1-yl)isoindole-1,3-dione as Monoamine Oxidase (MAO) and Cholinesterase (ChE) Inhibitors

Yiming Hu^a,†, Jiayu Xu^a,†, Min Tang^a, Yawen Liu^a, Liping Guan^a,*(), Qinghao Jin^b,*()

a Food and Pharmacy College, Zhejiang Ocean University, Zhoushan, Zhejiang 316022
b College of Nursing, Zhejiang Pharmaceutical University, Ningbo, Zhejiang 315153

Received:2023-11-24 Revised:2024-01-22 Published:2024-03-12
Contact: * E-mail: glp730@zjou.edu.cn; qhjin2012@163.com
About author:
^†These authors contributed equally to this work.
Supported by:
Fujian Provincial Key Laboratory of Innovative Drug Target Research(FJ-YW-2023KF04); National College Student Innovation and Entrepreneurship Training Program(202310340048)

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Abstract

A series of 2-(1,3-dioxoisoindolin-2-yl)-N-phenethylacetamide and 2-(3,4-dihydroisoquinolin-1-yl)isoindole- 1,3-dione derivatives were synthesized and their biological activities of monoamine oxidase (MAO) and cholinesterase (ChE) inhibition were evaluated. The experimental results showed that all compounds exhibited certain inhibitory activity against MAOs. Upon separate monoamine oxidase A (MAO-A) and monoamine oxidase A (MAO-B) activity were studied, the compounds displayed better inhibition activity against MAO-B and weaker inhibition activity against MAO-A. Among these, 2-(1,3-dioxoisoindolin-2-yl)-N-(4-fluorophenethyl)acetamide (2h) and 2-((7-methoxy-3,4-dihydroisoquinolin-1-yl)methyl)iso- indoline-1,3-dione (3d) exhibited the most significant inhibition of MAO-A and MAO-B, with IC₅₀ values of (3.87±0.59) and (3.35±0.53) μmol/L towards MAO, respectively. Results from cytotoxicity assays indicated that compounds with good inhi-bitory activity showed no cytotoxicity against L929 cells. Molecular docking of compounds 2h and 3d revealed significant interactions between the active analogs and amino acid residues of the protein receptors. Additionally, all compounds exhibited relatively weak inhibition activity against acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE).

Key words: 2-(1,3-dioxoisoindolin-2-yl)-N-phenethylacetamide, 2-(3,4-dihydroisoquinolin-1-yl)isoindole-1,3-dione, monoamine oxidase, cholinesterase, cytotoxicity, molecular docking

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Yiming Hu, Jiayu Xu, Min Tang, Yawen Liu, Liping Guan, Qinghao Jin. Design, Synthesis and Biological Activity Studies of 2-(1,3-Dioxoiso-indolin-2-yl)-N-phenethylacetamide and 2-(3,4-Dihydroisoquinolin-1-yl)isoindole-1,3-dione as Monoamine Oxidase (MAO) and Cholinesterase (ChE) Inhibitors[J]. Chinese Journal of Organic Chemistry, 2024, 44(6): 1907-1919.

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Compd.	R	Inhibition rate/%	IC₅₀/(μmol•L^–1)
2a	H	67.59	6.00±0.77
2b	4-CH₃	62.21	4.42±0.61
2c	2-OCH₃	41.83	14.03±1.14
2d	4-OCH₃	64.21	4.09±0.61
2e	3,4-(OCH₃)₂	58.82	5.23±0.72
2f	2-F	41.83	14.73±1.16
2g	3-F	68.63	3.64±0.56
2h	4-F	66.01	3.87±0.59
2i	4-Cl	86.27	6.34±0.95
2j	2-Br	60.13	6.18±0.79
2k	3-Br	65.36	4.94±0.60
2l	4-Br	35.95	15.93±1.45
3a	H	80.66	5.29±2.24
3b	4-CH₃	61.56	4.55±0.60
3c	2-OCH₃	38.57	13.5±1.55
3d	4-OCH₃	91.98	3.35±0.53
3e	3,4-(OCH₃)₂	52.72	9.40±1.76
3f	2-F	63.68	4.17±0.64
3g	3-F	79.25	3.91±0.60
3h	4-F	96.70	1.53±0.19
3i	4-Cl	79.48	3.94±1.43
3j	2-Br	87.27	3.10±0.36
3k	3-Br	76.42	4.86±0.69
3l	4-Br	50.47	9.58±0.44
Rasagiline	—	88.30	1.68±0.75

Compd.	R	Inhibition rate/%	IC₅₀/(μmol•L^–1)
2a	H	67.59	6.00±0.77
2b	4-CH₃	62.21	4.42±0.61
2c	2-OCH₃	41.83	14.03±1.14
2d	4-OCH₃	64.21	4.09±0.61
2e	3,4-(OCH₃)₂	58.82	5.23±0.72
2f	2-F	41.83	14.73±1.16
2g	3-F	68.63	3.64±0.56
2h	4-F	66.01	3.87±0.59
2i	4-Cl	86.27	6.34±0.95
2j	2-Br	60.13	6.18±0.79
2k	3-Br	65.36	4.94±0.60
2l	4-Br	35.95	15.93±1.45
3a	H	80.66	5.29±2.24
3b	4-CH₃	61.56	4.55±0.60
3c	2-OCH₃	38.57	13.5±1.55
3d	4-OCH₃	91.98	3.35±0.53
3e	3,4-(OCH₃)₂	52.72	9.40±1.76
3f	2-F	63.68	4.17±0.64
3g	3-F	79.25	3.91±0.60
3h	4-F	96.70	1.53±0.19
3i	4-Cl	79.48	3.94±1.43
3j	2-Br	87.27	3.10±0.36
3k	3-Br	76.42	4.86±0.69
3l	4-Br	50.47	9.58±0.44
Rasagiline	—	88.30	1.68±0.75

Compd.	R	Inhibition rate/%		IC₅₀/(μmol•L^–1) of MAO-B
Compd.	R	MAO-A	MAO-B	IC₅₀/(μmol•L^–1) of MAO-B
2a	H	58.06	76.80	5.20±1.83
2b	4-CH₃	22.58	65.46	7.27±0.86
2c	2-OCH₃	42.42	38.85
2d	4-OCH₃	32.26	61.60	7.47±1.62
2e	3,4-(OCH₃)₂	22.64	78.98	5.58±0.75
2f	2-F	21.21	44.94
2g	3-F	20.97	30.15
2h	4-F	64.52	75.26	5.02±0.70
2i	4-Cl	29.03	63.14	7.36±1.75
2j	2-Br	66.04	10.83
2k	3-Br	3.23	30.41
2l	4-Br	60.61	31.44
3a	H	31.25	1.37
3b	4-CH₃	34.38	21.92
3c	2-OCH₃	69.7	69.59	7.41±2.76
3d	4-OCH₃	78.75	89.04	4.82±0.83
3e	3,4-(OCH₃)₂	27.42	74.23	4.94±0.69
3f	2-F	28.13	8.90
3g	3-F	25.00	71.23	4.84±1.25
3h	4-F	15.63	35.65
3i	4-Cl	4.69	72.60	4.86±1.35
3j	2-Br	21.88	49.32
3k	3-Br	34.38	78.08	5.40±0.73
3l	4-Br	26.56	35.62

Compd.	R	Inhibition rate/%		IC₅₀/(μmol•L^–1) of MAO-B
Compd.	R	MAO-A	MAO-B	IC₅₀/(μmol•L^–1) of MAO-B
2a	H	58.06	76.80	5.20±1.83
2b	4-CH₃	22.58	65.46	7.27±0.86
2c	2-OCH₃	42.42	38.85
2d	4-OCH₃	32.26	61.60	7.47±1.62
2e	3,4-(OCH₃)₂	22.64	78.98	5.58±0.75
2f	2-F	21.21	44.94
2g	3-F	20.97	30.15
2h	4-F	64.52	75.26	5.02±0.70
2i	4-Cl	29.03	63.14	7.36±1.75
2j	2-Br	66.04	10.83
2k	3-Br	3.23	30.41
2l	4-Br	60.61	31.44
3a	H	31.25	1.37
3b	4-CH₃	34.38	21.92
3c	2-OCH₃	69.7	69.59	7.41±2.76
3d	4-OCH₃	78.75	89.04	4.82±0.83
3e	3,4-(OCH₃)₂	27.42	74.23	4.94±0.69
3f	2-F	28.13	8.90
3g	3-F	25.00	71.23	4.84±1.25
3h	4-F	15.63	35.65
3i	4-Cl	4.69	72.60	4.86±1.35
3j	2-Br	21.88	49.32
3k	3-Br	34.38	78.08	5.40±0.73
3l	4-Br	26.56	35.62

2-(1,3-二氧代异吲哚啉-2-基)-N-苯乙酰胺和2-(3,4-二氢异喹啉-1-基)异吲哚-1,3-二酮类单胺氧化酶(MAO)和胆碱酯酶(ChE)抑制剂的设计、合成和生物活性研究

Design, Synthesis and Biological Activity Studies of 2-(1,3-Dioxoiso-indolin-2-yl)-N-phenethylacetamide and 2-(3,4-Dihydroisoquinolin-1-yl)isoindole-1,3-dione as Monoamine Oxidase (MAO) and Cholinesterase (ChE) Inhibitors

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