Synthesis and Biological Activities of New 4-PhenylanilinesContaining the Diphenyl Ether Moiety

doi:10.6023/cjoc201904049

Chinese Journal of Organic Chemistry ›› 2019, Vol. 39 ›› Issue (10): 2851-2859.DOI: 10.6023/cjoc201904049 Previous Articles Next Articles

ARTICLE

含二苯醚结构的联苯胺类衍生物的合成及活性研究

汪万强^a, 程兰^a, 彭宏英^a, 姚维忠^a, 张锐^a, 陈宬^b^*(), 程华^a^*()

^a 湖北文理学院化学化工与食品科学学院襄阳 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

收稿日期:2019-04-19 修回日期:2019-05-23 发布日期:2019-06-06
通讯作者: 陈宬,程华 E-mail:chengchen@whut.edu.cn;cch510@126.com
基金资助:
国家自然科学基金(21502062);湖北文理学院教师科研能力培育基金(2018kypy001);湖北文理学院学科开放基金资助项目(XK2019039)

Synthesis and Biological Activities of New 4-PhenylanilinesContaining the Diphenyl Ether Moiety

Wang Wanqiang^a, Cheng Lan^a, Peng Hongying^a, Yao Weizhong^a, Zhang Rui^a, Chen Cheng^b^*(), Cheng Hua^a^*()

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

Received:2019-04-19 Revised:2019-05-23 Published:2019-06-06
Contact: Chen Cheng,Cheng Hua E-mail:chengchen@whut.edu.cn;cch510@126.com
Supported by:
Project supported by the National Natural Science Foundation of China(21502062);The Teachers' Scientific Research Ability Cultivation Fund of Hubei University of Arts and Science(2018kypy001);The Open Foundation of Discipline of Hubei University of Arts and Science(XK2019039)

According to the principle of "splicing-up" bioactive substructures, a new series of target compounds were designed and synthesized by incorporating a diphenyl ether moiety into 4-phenylanilines. Moreover, the structures of the synthesized compounds were confirmed by ¹H NMR, ¹³C NMR, HRMS and melting points measurements. The inhibitory activities of these compounds were evaluated against succinate-cytochrome reductase (SCR). Based on the bioassay results, target compound N-(4-(2-chloro-4-(trifluoromethyl)phenoxy)-3-fluorophenyl)-[1,1'-biphenyl]-4-amine (3o) exhibited an inhibition rate of 46.44% at a concentration of 10 μmol?L ^–1, which demonstrated potential values for further investigations.

Key words: 4-phenylanilines, diphenyl ether, synthesis, biological activities

Cite this article

Wang Wanqiang, Cheng Lan, Peng Hongying, Yao Weizhong, Zhang Rui, Chen Cheng, Cheng Hua. Synthesis and Biological Activities of New 4-PhenylanilinesContaining the Diphenyl Ether Moiety[J]. Chinese Journal of Organic Chemistry, 2019, 39(10): 2851-2859.

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Fig. & Tab. 5

References 47

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Entry	[Cu] (equiv.)	Base (equiv.)	Solvent	Time/ h	Yield^a/ %
1	Cu(OAc)₂ (1.00)	K₂CO₃ (2.00)	DMF	60	65
2	Cu(OAc)₂?H₂O (1.00)	K₂CO₃ (2.00)	DMF	60	58
3	CuCl₂ (1.00)	K₂CO₃ (2.00)	DMF	60	Trace
4	CuCl₂?2H₂O (1.00)	K₂CO₃ (2.00)	DMF	60	Trace
5	CuBr₂ (1.00)	K₂CO₃ (2.00)	DMF	60	Trace
6	CuCl (1.00)	K₂CO₃ (2.00)	DMF	60	Trace
7	CuBr (1.00)	K₂CO₃ (2.00)	DMF	60	Trace
8	CuI (1.00)	K₂CO₃ (2.00)	DMF	60	Trace
9	Cu(OAc)₂ (1.00)	Cs₂CO₃ (2.00)	DMF	60	Trace
10	Cu(OAc)₂ (1.00)	Pyridine (2.00)	DMF	60	Trace
11	Cu(OAc)₂ (1.00)	Et₃N (2.00)	DMF	48	75
12	Cu(OAc)₂ (1.00)	Et₃N (2.00)	DCM	48	84
13	Cu(OAc)₂ (1.00)	Et₃N (2.00)	MeCN	48	90
14	Cu(OAc)₂ (0.50)	Et₃N (2.00)	MeCN	72	70
15	Cu(OAc)₂ (0.25)	Et₃N (2.00)	MeCN	72	65
16	Cu(OAc)₂ (1.00)	Et₃N (2.00)	MeCN	72	30

Entry	[Cu] (equiv.)	Base (equiv.)	Solvent	Time/ h	Yield^a/ %
1	Cu(OAc)₂ (1.00)	K₂CO₃ (2.00)	DMF	60	65
2	Cu(OAc)₂?H₂O (1.00)	K₂CO₃ (2.00)	DMF	60	58
3	CuCl₂ (1.00)	K₂CO₃ (2.00)	DMF	60	Trace
4	CuCl₂?2H₂O (1.00)	K₂CO₃ (2.00)	DMF	60	Trace
5	CuBr₂ (1.00)	K₂CO₃ (2.00)	DMF	60	Trace
6	CuCl (1.00)	K₂CO₃ (2.00)	DMF	60	Trace
7	CuBr (1.00)	K₂CO₃ (2.00)	DMF	60	Trace
8	CuI (1.00)	K₂CO₃ (2.00)	DMF	60	Trace
9	Cu(OAc)₂ (1.00)	Cs₂CO₃ (2.00)	DMF	60	Trace
10	Cu(OAc)₂ (1.00)	Pyridine (2.00)	DMF	60	Trace
11	Cu(OAc)₂ (1.00)	Et₃N (2.00)	DMF	48	75
12	Cu(OAc)₂ (1.00)	Et₃N (2.00)	DCM	48	84
13	Cu(OAc)₂ (1.00)	Et₃N (2.00)	MeCN	48	90
14	Cu(OAc)₂ (0.50)	Et₃N (2.00)	MeCN	72	70
15	Cu(OAc)₂ (0.25)	Et₃N (2.00)	MeCN	72	65
16	Cu(OAc)₂ (1.00)	Et₃N (2.00)	MeCN	72	30

Entry	Compd.	R¹	R²	Yield^a/%	I^b/%
1	3a	H	H	90	30.42
2	3b	4-Br	H	76	36.95
3	3c	2,4-Cl₂	H	71	36.09
4	3d	2-Cl-4-CF₃	H	86	39.01
5	3e	2-Br-4-Cl	H	74	32.16
6	3f	2,4,6-Cl₃	2-Cl	94	13.72
7	3g	2,4-Cl₂	2-Cl	69	6.30
8	3h	2-Me-4-Cl	2-Cl	67	12.71
9	3i	2-Cl-4-CF₃	2-Cl	74	24.47
10	3j	2-Br-4-Cl	2-Cl	68	6.81
11	3k	2-Naphthyl^c	2-Cl	76	5.73
12	3l	1-Br-2-naphthyl^c	2-Cl	70	1.91
13	3m	2,4-Cl₂	2-F	75	37.70
14	3n	2-Me-4-Cl	2-F	95	37.39
15	3o	2-Cl-4-CF₃	2-F	73	46.44
16	3p	2,4,6-Cl₃	2-F	70	16.02
17	3q	2-Naphthyl^c	2-F	65	20.59
18	3r	1-Br-2-naphthyl^c	2-F	76	7.62
19	3s	2,4-Cl₂	2,6-Cl₂	50	4.07
20	3t	2-Br-4-Cl	2,6-Cl₂	54	10.07
21	3u	2-Naphthyl^c	2,6-Cl₂	78	26.09
22	3v	1-Br-2-naphthyl^c	2,6-Cl₂	71	3.74
23	3w	2,4-Cl₂	2,6-F₂	81	38.96
24	3x	4-Cl-2-Me	2,6-F₂	68	37.78
25	3y	2-Br-4-Cl	2,6-F₂	62	43.25
26	3z	2-Naphthyl^c	2,6-F₂	61	43.20
27	3a'	1-Br-2-naphthyl^c	2,6-F₂	68	10.23
28	嘧菌酯^d				95.95

Entry	Compd.	R¹	R²	Yield^a/%	I^b/%
1	3a	H	H	90	30.42
2	3b	4-Br	H	76	36.95
3	3c	2,4-Cl₂	H	71	36.09
4	3d	2-Cl-4-CF₃	H	86	39.01
5	3e	2-Br-4-Cl	H	74	32.16
6	3f	2,4,6-Cl₃	2-Cl	94	13.72
7	3g	2,4-Cl₂	2-Cl	69	6.30
8	3h	2-Me-4-Cl	2-Cl	67	12.71
9	3i	2-Cl-4-CF₃	2-Cl	74	24.47
10	3j	2-Br-4-Cl	2-Cl	68	6.81
11	3k	2-Naphthyl^c	2-Cl	76	5.73
12	3l	1-Br-2-naphthyl^c	2-Cl	70	1.91
13	3m	2,4-Cl₂	2-F	75	37.70
14	3n	2-Me-4-Cl	2-F	95	37.39
15	3o	2-Cl-4-CF₃	2-F	73	46.44
16	3p	2,4,6-Cl₃	2-F	70	16.02
17	3q	2-Naphthyl^c	2-F	65	20.59
18	3r	1-Br-2-naphthyl^c	2-F	76	7.62
19	3s	2,4-Cl₂	2,6-Cl₂	50	4.07
20	3t	2-Br-4-Cl	2,6-Cl₂	54	10.07
21	3u	2-Naphthyl^c	2,6-Cl₂	78	26.09
22	3v	1-Br-2-naphthyl^c	2,6-Cl₂	71	3.74
23	3w	2,4-Cl₂	2,6-F₂	81	38.96
24	3x	4-Cl-2-Me	2,6-F₂	68	37.78
25	3y	2-Br-4-Cl	2,6-F₂	62	43.25
26	3z	2-Naphthyl^c	2,6-F₂	61	43.20
27	3a'	1-Br-2-naphthyl^c	2,6-F₂	68	10.23
28	嘧菌酯^d				95.95

含二苯醚结构的联苯胺类衍生物的合成及活性研究

Synthesis and Biological Activities of New 4-PhenylanilinesContaining the Diphenyl Ether Moiety

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