Synthesis and Biological Activities of Coenzyme Q Derivatives Containing (4-Aryloxylaryl)amino Moiety

doi:10.6023/cjoc202011026

Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (5): 2045-2054.DOI: 10.6023/cjoc202011026 Previous Articles Next Articles

ARTICLES

含4-氨基二芳醚结构的辅酶Q衍生物的合成与生物活性研究

秦啸天^a, 张俊朝^a, 何钰晴^a, 张锐^a, 程华^a^,^*(), 陈宬^b^,^*(), 秦鑫^c^,^*()

a 湖北文理学院化学化工与食品科学学院湖北襄阳 441053
b 武汉理工大学材料复合新技术国家重点实验室武汉 430070
c 湖北文理学院医学院湖北襄阳 441053

收稿日期:2020-11-20 修回日期:2020-12-21 发布日期:2021-02-22
通讯作者: 程华, 陈宬, 秦鑫
基金资助:
湖北省教育厅重点项目(D20192601); 湖北文理学院创新团队培育基金(2020kypyt004); 国家级大学生创新创业训练计划(201910519006); 湖北文理学院科研启动基金(2059057)

Synthesis and Biological Activities of Coenzyme Q Derivatives Containing (4-Aryloxylaryl)amino Moiety

Xiaotian Qin^a, Junchao Zhang^a, Yuqing He^a, Rui Zhang^a, Hua Cheng^a^,^*(), Cheng Chen^b^,^*(), Xin Qin^c^,^*()

a Department of Chemical Engineering and Food Science, Hubei University of Arts and Science, Xiangyang, Hubei 441053
b State Key Laboratory of Advanced Technology for Materials Synthesis and Processing, Wuhan University of Technology, Wuhan 430070
c Medicine College of Hubei University of Arts and Science, Xiangyang, Hubei 441053

Received:2020-11-20 Revised:2020-12-21 Published:2021-02-22
Contact: Hua Cheng, Cheng Chen, Xin Qin
About author:
* Corresponding authors. E-mail: cch510@126.com;
E-mail: chengchen@whut.edu.cn;
E-mail: 543755712@qq.com
Supported by:
Key Project of Hubei Provincial Department of Education(D20192601); Innovation Team Cultivation Fund of Hubei University of Arts and Sciences(2020kypyt004); National Undergraduate Innovation and Entrepreneurship Training Program(201910519006); Starting Research Fund of Hubei University of Arts and Science(2059057)

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Abstract

Coenzyme Q is a class of compounds that naturally exist in a variety of biological cells and have important physiological functions. They have attracted extensive attention due to their own biochemical and pharmacological effects. In addition, the diaryl ether skeleton is widely present in many biologically active molecules such as medicines and pesticides. In view of the unique structures and physiological functions of coenzyme Q, combined with the extensive biological activity of diaryl ether fragments and the basis of our previous work, a series of coenzyme Q derivatives containing (4-aryloxylaryl)- amino moiety were designed and synthesized. The structures of the target compounds were confirmed by nuclear magnetic resonance spectroscopy (¹H NMR and ¹³C NMR), high resolution mass spectrometry (HRMS) and melting point measurements. Subsequently, the in vitro inhibitory activities of these compounds against porcine heart succinate-cytochrome c oxidoreductase (SCR) as well as their in vivobactericidal, herbicidal and insecticidal activities were evaluated. The bioassay results indicated that some compounds demonstrated certain biological activity, showing the potential values for further investigations.

Key words: coenzyme Q, derivative, diaryl ether, synthesis, biological activity

Cite this article

Xiaotian Qin, Junchao Zhang, Yuqing He, Rui Zhang, Hua Cheng, Cheng Chen, Xin Qin. Synthesis and Biological Activities of Coenzyme Q Derivatives Containing (4-Aryloxylaryl)amino Moiety[J]. Chinese Journal of Organic Chemistry, 2021, 41(5): 2045-2054.

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Entry	[Pd] (mol%)	Ligand (mol%)	Base (mmol)	Solvent (mL)	Yield^a/%
1	Pd(OAc)₂ (5)	XPhos (10)	Cs₂CO₃ (0.15)	Toluene (3.3)	33
2	Pd(OAc)₂ (5)	XPhos (10)	Cs₂CO₃ (0.15)	Toluene (5.0)	48
3	Pd(OAc)₂ (5)	XPhos (10)	Cs₂CO₃ (0.15)	Toluene (6.6)	38
4	Pd(OAc)₂ (10)	XPhos (10)	Cs₂CO₃ (0.15)	Toluene (5.0)	62
5	Pd(OAc)₂ (10)	XPhos (15)	Cs₂CO₃ (0.15)	Toluene (5.0)	63
6	Pd(OAc)₂ (10)	Brettphos (10)	Cs₂CO₃ (0.15)	Toluene (5.0)	Trace
7	Pd(OAc)₂ (10)	Xantphos (10)	Cs₂CO₃ (0.15)	Toluene (5.0)	68
8	Pd(OAc)₂ (10)	^tBuBrettphos (10)	Cs₂CO₃ (0.15)	Toluene (5.0)	Trace
9	Pd(OAc)₂ (10)	RuPhos (10)	Cs₂CO₃ (0.15)	Toluene (5.0)	70
10	PdCl₂ (10)	RuPhos (10)	Cs₂CO₃ (0.15)	Toluene (5.0)	45
11	Pd₂(dba)₃ (10)	RuPhos (10)	Cs₂CO₃ (0.15)	Toluene (5.0)	60
12	Pd(OAc)₂ (10)	RuPhos (10)	K₂CO₃(0.15)	Toluene (5.0)	82
13	Pd(OAc)₂ (10)	RuPhos (10)	KO^tBu (0.15)	Toluene (5.0)	20
14	Pd(OAc)₂ (10)	RuPhos (10)	NaH (0.15)	Toluene (5.0)	25
15	Pd(OAc)₂ (10)	RuPhos (10)	K₂CO₃ (0.10)	Toluene (5.0)	72
16	Pd(OAc)₂ (10)	RuPhos (10)	K₂CO₃ (0.20)	Toluene (5.0)	79
17	Pd(OAc)₂ (10)	RuPhos (10)	K₂CO₃ (0.25)	Toluene (5.0)	77
18	Pd(OAc)₂ (10)	—	K₂CO₃ (0.15)	Toluene (5.0)	Trace
19	—	RuPhos (10)	K₂CO₃ (0.15)	Toluene (5.0)	Trace

Entry	[Pd] (mol%)	Ligand (mol%)	Base (mmol)	Solvent (mL)	Yield^a/%
1	Pd(OAc)₂ (5)	XPhos (10)	Cs₂CO₃ (0.15)	Toluene (3.3)	33
2	Pd(OAc)₂ (5)	XPhos (10)	Cs₂CO₃ (0.15)	Toluene (5.0)	48
3	Pd(OAc)₂ (5)	XPhos (10)	Cs₂CO₃ (0.15)	Toluene (6.6)	38
4	Pd(OAc)₂ (10)	XPhos (10)	Cs₂CO₃ (0.15)	Toluene (5.0)	62
5	Pd(OAc)₂ (10)	XPhos (15)	Cs₂CO₃ (0.15)	Toluene (5.0)	63
6	Pd(OAc)₂ (10)	Brettphos (10)	Cs₂CO₃ (0.15)	Toluene (5.0)	Trace
7	Pd(OAc)₂ (10)	Xantphos (10)	Cs₂CO₃ (0.15)	Toluene (5.0)	68
8	Pd(OAc)₂ (10)	^tBuBrettphos (10)	Cs₂CO₃ (0.15)	Toluene (5.0)	Trace
9	Pd(OAc)₂ (10)	RuPhos (10)	Cs₂CO₃ (0.15)	Toluene (5.0)	70
10	PdCl₂ (10)	RuPhos (10)	Cs₂CO₃ (0.15)	Toluene (5.0)	45
11	Pd₂(dba)₃ (10)	RuPhos (10)	Cs₂CO₃ (0.15)	Toluene (5.0)	60
12	Pd(OAc)₂ (10)	RuPhos (10)	K₂CO₃(0.15)	Toluene (5.0)	82
13	Pd(OAc)₂ (10)	RuPhos (10)	KO^tBu (0.15)	Toluene (5.0)	20
14	Pd(OAc)₂ (10)	RuPhos (10)	NaH (0.15)	Toluene (5.0)	25
15	Pd(OAc)₂ (10)	RuPhos (10)	K₂CO₃ (0.10)	Toluene (5.0)	72
16	Pd(OAc)₂ (10)	RuPhos (10)	K₂CO₃ (0.20)	Toluene (5.0)	79
17	Pd(OAc)₂ (10)	RuPhos (10)	K₂CO₃ (0.25)	Toluene (5.0)	77
18	Pd(OAc)₂ (10)	—	K₂CO₃ (0.15)	Toluene (5.0)	Trace
19	—	RuPhos (10)	K₂CO₃ (0.15)	Toluene (5.0)	Trace

Entry		Compd.	R¹		R²		Yield^a/%		I^b/%
1		4a	H		H		80		13.95
2		4b	4-CN		H		56		19.99
3		4c	4-OCF₃		H		60		9.20
4		4d	2-CN		H		72		42.94
5		4e	2,4-Cl₂		H		75		9.59
6		4f	2-Cl-4-CF₃		H		67		14.25
7		4g	2-Naphthyl^c		H		81		9.33
8		4h	2,4-Cl₂		2-F		58		14.74
9		4i	2-Cl-4-CH₃		2-F		63		2.15
10		4j	2,4,6-Cl₃		2-F		57		7.65
11		4k	2-Naphthyl^c		2-F		73		12.90
12		4l	2,4-Cl₂		2-Cl		60		8.91
13		4m	2-Cl-4-CF₃		2-Cl		65		39.83
14		4n	2-Cl-4-CH₃		2-Cl		57		10.95
15		4o	2,4,6-Cl₃		2-Cl		72		3.48
16	4p			2-Naphthyl^c		2-Cl		75		5.21
17	4q			2,4-Cl₂		2,6-F₂		62		3.60
18	4r			2,4,6-Cl₃		2,6-F₂		65		1.18
19	4s			2-Naphthyl^c		2,6-F₂		62		11.47
20	4t			2,4-Cl₂		2,6-Cl₂		91		6.62
21	4u			2-Cl-4-CF₃		2,6-Cl₂		67		9.37
22	4v			2,4,6-Cl₃		2,6-Cl₂		53		9.47
23	4w			2-Naphthyl		2,6-Cl₂		60		8.26
24	Azoxystrobin^d									92.56

Entry		Compd.	R¹		R²		Yield^a/%		I^b/%
1		4a	H		H		80		13.95
2		4b	4-CN		H		56		19.99
3		4c	4-OCF₃		H		60		9.20
4		4d	2-CN		H		72		42.94
5		4e	2,4-Cl₂		H		75		9.59
6		4f	2-Cl-4-CF₃		H		67		14.25
7		4g	2-Naphthyl^c		H		81		9.33
8		4h	2,4-Cl₂		2-F		58		14.74
9		4i	2-Cl-4-CH₃		2-F		63		2.15
10		4j	2,4,6-Cl₃		2-F		57		7.65
11		4k	2-Naphthyl^c		2-F		73		12.90
12		4l	2,4-Cl₂		2-Cl		60		8.91
13		4m	2-Cl-4-CF₃		2-Cl		65		39.83
14		4n	2-Cl-4-CH₃		2-Cl		57		10.95
15		4o	2,4,6-Cl₃		2-Cl		72		3.48
16	4p			2-Naphthyl^c		2-Cl		75		5.21
17	4q			2,4-Cl₂		2,6-F₂		62		3.60
18	4r			2,4,6-Cl₃		2,6-F₂		65		1.18
19	4s			2-Naphthyl^c		2,6-F₂		62		11.47
20	4t			2,4-Cl₂		2,6-Cl₂		91		6.62
21	4u			2-Cl-4-CF₃		2,6-Cl₂		67		9.37
22	4v			2,4,6-Cl₃		2,6-Cl₂		53		9.47
23	4w			2-Naphthyl		2,6-Cl₂		60		8.26
24	Azoxystrobin^d									92.56

含4-氨基二芳醚结构的辅酶Q衍生物的合成与生物活性研究

Synthesis and Biological Activities of Coenzyme Q Derivatives Containing (4-Aryloxylaryl)amino Moiety

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