新型含吡啶基3-硫醚-4-吲哚亚氨基-4H-1,2,4-三唑衍生物的设计、合成及体外生物活性评价

doi:10.6023/cjoc202008057

有机化学 ›› 2021, Vol. 41 ›› Issue (4): 1670-1682.DOI: 10.6023/cjoc202008057 上一篇下一篇

研究论文

新型含吡啶基3-硫醚-4-吲哚亚氨基-4H-1,2,4-三唑衍生物的设计、合成及体外生物活性评价

漆亚云^a, 刘佳敏^a, 李成朋^a, 胡伟男^a, 唐思雨^a, 邵利辉^a, 王贞超^a^,^b^,^*(), 欧阳贵平^a^,^b^,^c^,^*()

a 贵州大学药学院贵阳 550025
b 贵州医科大学药用植物功效与利用国家重点实验室贵阳 550014
c 贵州省合成药物工程实验室贵阳 550025

收稿日期:2020-08-31 修回日期:2020-11-06 发布日期:2020-12-10
通讯作者: 王贞超, 欧阳贵平
作者简介:
† 共同第一作者(These anthors contributed equally to this work).
基金资助:
国家自然科学基金(21867004); 药用植物功效与利用国家重点实验室(FAMP201801K); 和贵州省科技计划项目(No.黔科合平台人才[2018]5781号)()

Novel 3-Thioether-4-indolimino-4H-1,2,4-triazole Derivatives Bearing Pyridyl Moiety: Design, Synthesis and Bioactivity Evaluation in vitro

Yayun Qi^a, Jiamin Liu^a, Chenpeng Li^a, Weinan Hu^a, Siyu Tang^a, Lihui Shao^a, Zhenchao Wang^a^,^b^,^*(), Guiping Ouyang^a^,^b^,^c^,^*()

a School of Pharmaceutical Sciences, Guizhou University, Guiyang 550025
b State Key Laboratory of Functions and Applications of Medicinal Plants, Guizhou Medical University, Guiyang 550014
c Guizhou Engineering Laboratory for Synthetic Drugs, Guiyang 550025

Received:2020-08-31 Revised:2020-11-06 Published:2020-12-10
Contact: Zhenchao Wang, Guiping Ouyang
About author:
* Corresponding authors. E-mail: wzc.4884@163.com;
E-mail: oygp710@163.com
Supported by:
Natural Science Foundation of China(21867004); State Key Laboratory of Functions and Applications of Medicinal Plants(FAMP201801K); Guizhou Science technology program for Platform and Talents(No.20185781)()

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摘要/Abstract

设计、合成了一系列含吡啶基的新型3-硫醚-4-吲哚亚氨基-4H-1,2,4-三唑衍生物17a~17r. 采用噻唑蓝(MTT)法对目标化合物在人类四种癌细胞A549、PC-3、HepG2、K562和大鼠正常肾细胞NRK-52E进行抗增殖活性评价. 结果显示部分化合物表现出一定的抗增殖活性, 其中乙基(E)-2-((4-(((2-氯-1-乙基-1H-吲哚-3-基)亚甲基)氨基)-5-(吡啶-4-基)-4H-1,2,4-三唑-3-基)硫代)乙酸酯(17k)对PC-3表现出较好的抗增殖活性, IC₅₀值为9.90 μmol/L, 且对NRK-52E的细胞增殖毒性低于对照药5-氟尿嘧啶. 同时, 采用细胞迁移试验、4,6-二脒基-2-苯基吲哚(DAPI)染色、线粒体膜电位分析以及细胞凋亡、周期分析, 进一步研究了化合物 17k的作用机制, 证明化合物17k能够有效抑制肿瘤细胞的迁移, 诱发细胞凋亡, 还可以浓度依赖性方式将人前列腺癌细胞PC-3的细胞周期阻滞在G2期. 此外, 还探究了目标化合物对水稻白叶枯病菌(Xanthomonas oryzae pv. Oryzae, Xoo)的抑制活性, 初步抗菌活性结果显示: 化合物17b、17e和17h在50和100 μg/mL时, 对水稻白叶枯病菌表现出一定的抑制活性, 优于对照药叶枯唑(BMT)和噻菌铜(TDC).

关键词: 1,2,4-三唑, 吲哚, 抗肿瘤活性, 杀菌活性

A series of novel 3-thioether-4-indolimino-4H-1,2,4-triazole derivatives bearing pyridyl moiety (17a~17r) have been designed, synthesized and evaluated for antiproliferative activities against four human cancer cells A549, PC-3, HepG2 and K562, and normal rat kidney cells NRK-52E using methyl thiazolyl tetrazolium (MTT) assay. The results showed that some compounds exhibited moderate antiproliferative activities against four cancer cells. Among these derivatives, ethyl (E)-2-((4-(((2-chloro-1-ethyl-1H-indol-3-yl)methylene)amino)-5-(pyridin-4-yl)-4H-1,2,4-triazol-3-yl)thio)acetate (17k) showed the most potent antiproliferative activity against PC-3 cells with IC₅₀value of 9.90 μmol/L, and the toxicities of compound 17k to NRK-52E cells were significantly lower than the positive control 5-fluorouracil. Meanwhile, the cell migration assay, 4,6-diamidino-2-phenylindole (DAPI) staining, mitochondrial membrane potential analysis, cell apoptosis and cell cycle analysis were carried out to further studied the mechanism of compound 17k, which demonstrated that compound 17k can effectively inhibit tumor cell migration and significantly induce cell apoptosis, arrest PC-3 cells in the G2 stage in a dose-dependent manner. In addition, the antibacterial tests of target compounds against Xanthomonas oryzae pv. oryzae (Xoo) were also explored. The preliminary antibacterial activity results showed that compounds 17b, 17e and 17h displayed a noteworthy inhibition rate against Xoo compared to standard drugs bismerthiazol (BMT) and thiodiazole copper (TDC) at 50 and 100 μg/mL.

Key words: 1,2,4-triazole, indole, antiproliferative activity, bactericidal activity

引用此文

漆亚云, 刘佳敏, 李成朋, 胡伟男, 唐思雨, 邵利辉, 王贞超, 欧阳贵平. 新型含吡啶基3-硫醚-4-吲哚亚氨基-4H-1,2,4-三唑衍生物的设计、合成及体外生物活性评价[J]. 有机化学, 2021, 41(4): 1670-1682.

Yayun Qi, Jiamin Liu, Chenpeng Li, Weinan Hu, Siyu Tang, Lihui Shao, Zhenchao Wang, Guiping Ouyang. Novel 3-Thioether-4-indolimino-4H-1,2,4-triazole Derivatives Bearing Pyridyl Moiety: Design, Synthesis and Bioactivity Evaluation in vitro[J]. Chinese Journal of Organic Chemistry, 2021, 41(4): 1670-1682.

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Compd.	Inhibitory activity^a/% at 10 μmol/L
Compd.	A549	PC-3	HepG2	K562
17a	17.02±3.33	27.76±5.09	4.60±6.71	5.82±2.12
17b	17.56±5.63	37.13±3.89	8.86±5.78	12.52±5.33
17c	14.89±4.85	40.04±4.85	30.28±4.85	27.03±4.85
17d	22.29±1.28	37.63±6.32	9.28±5.90	39.34±2.53
17e	16.13±2.55	27.62±3.56	6.03±4.71	11.62±2.16
17f	18.59±6.34	31.38±4.78	5.50±6.57	10.64±2.69
17g	11.11±3.22	25.59±2.70	6.52±9.90	13.00±5.37
17h	14.62±2.96	26.71±5.83	11.95±4.21	7.79±0.83
17i	10.04±3.34	18.46±6.41	9.15±4.67	14.94±5.38
17j	10.51±6.97	14.22±2.86	14.04±1.6	10.06±3.57
17k	36.90±3.46	32.98±2.29	52.80±2.40	29.33±1.96
17l	36.52±3.44	29.74±5.89	21.25±6.46	12.10±0.37
17m	24.16±5.60	36.98±4.31	12.65±5.27	16.12±5.50
17n	12.39±4.72	27.96±2.90	11.81±5.44	20.57±2.98
17o	22.99±8.21	40.04±7.26	11.30±4.48	14.96±7.78
17p	23.66±8.70	53.40±8.89	11.69±5.56	27.18±6.34
17q	30.59±6.66	36.11±1.62	10.52±1.38	18.05±1.07
17r	48.88±5.19	43.30±5.54	9.59±5.59	26.88±5.39
5-Fu^b	47.43±1.39	39.47±3.43	37.01±2.12	29.61±5.62

Compd.	Inhibitory activity^a/% at 10 μmol/L
Compd.	A549	PC-3	HepG2	K562
17a	17.02±3.33	27.76±5.09	4.60±6.71	5.82±2.12
17b	17.56±5.63	37.13±3.89	8.86±5.78	12.52±5.33
17c	14.89±4.85	40.04±4.85	30.28±4.85	27.03±4.85
17d	22.29±1.28	37.63±6.32	9.28±5.90	39.34±2.53
17e	16.13±2.55	27.62±3.56	6.03±4.71	11.62±2.16
17f	18.59±6.34	31.38±4.78	5.50±6.57	10.64±2.69
17g	11.11±3.22	25.59±2.70	6.52±9.90	13.00±5.37
17h	14.62±2.96	26.71±5.83	11.95±4.21	7.79±0.83
17i	10.04±3.34	18.46±6.41	9.15±4.67	14.94±5.38
17j	10.51±6.97	14.22±2.86	14.04±1.6	10.06±3.57
17k	36.90±3.46	32.98±2.29	52.80±2.40	29.33±1.96
17l	36.52±3.44	29.74±5.89	21.25±6.46	12.10±0.37
17m	24.16±5.60	36.98±4.31	12.65±5.27	16.12±5.50
17n	12.39±4.72	27.96±2.90	11.81±5.44	20.57±2.98
17o	22.99±8.21	40.04±7.26	11.30±4.48	14.96±7.78
17p	23.66±8.70	53.40±8.89	11.69±5.56	27.18±6.34
17q	30.59±6.66	36.11±1.62	10.52±1.38	18.05±1.07
17r	48.88±5.19	43.30±5.54	9.59±5.59	26.88±5.39
5-Fu^b	47.43±1.39	39.47±3.43	37.01±2.12	29.61±5.62

Compd.	IC₅₀^a/(μmol?L^-1)
Compd.	A549	PC-3	HepG2	K562
17b	25.02±6.63	24.97±8.11	43.02±7.61	18.32±4.41
17c	31.77±6.66	12.95±0.83	23.12±6.70	11.86±3.67
17d	15.45±1.48	26.31±8.86	17.99±1.83	14.39±0.65
17k	14.22±0.60	9.90±3.85	11.36±2.72	13.70±0.42
17l	16.23±3.34	17.54±5.00	22.22±0.92	37.23±7.64
17o	21.78±7.08	31.25±8.70	41.15±5.11	22.45±3.51
17p	29.96±3.49	26.60±8.06	17.63±8.92	58.49±8.25
17r	23.11±9.21	16.28±3.82	21.37±4.49	28.14±3.19
5-Fu^b	6.29±1.12	11.84±1.90	15.47±4.23	18.06±4.61

Compd.	IC₅₀^a/(μmol?L^-1)
Compd.	A549	PC-3	HepG2	K562
17b	25.02±6.63	24.97±8.11	43.02±7.61	18.32±4.41
17c	31.77±6.66	12.95±0.83	23.12±6.70	11.86±3.67
17d	15.45±1.48	26.31±8.86	17.99±1.83	14.39±0.65
17k	14.22±0.60	9.90±3.85	11.36±2.72	13.70±0.42
17l	16.23±3.34	17.54±5.00	22.22±0.92	37.23±7.64
17o	21.78±7.08	31.25±8.70	41.15±5.11	22.45±3.51
17p	29.96±3.49	26.60±8.06	17.63±8.92	58.49±8.25
17r	23.11±9.21	16.28±3.82	21.37±4.49	28.14±3.19
5-Fu^b	6.29±1.12	11.84±1.90	15.47±4.23	18.06±4.61

Compd.	R¹	R²	R³	R⁴	IC₅₀^a/(μmol?L^–1)
Compd.	R¹	R²	R³	R⁴	PC-3	NRK-52E
17a	H	o-Pyridyl	H	OCH₂CH₃	23.85±5.46	38.78±3.56
17b	H	o-Pyridyl	H	OCH₂CH₂CH₃	24.97±8.11	33.23±3.51
17c	H	o-Pyridyl	Cl	OCH₂CH₃	12.95±0.83	48.83±1.95
17d	H	o-Pyridyl	Cl	OCH₂CH₂CH₃	26.31±8.86	33.05±2.46
17e	CH₃	o-Pyridyl	Cl	OCH₂CH₃	27.61±3.45	45.41±3.20
17f	CH₃	o-Pyridyl	Cl	OCH₂CH₂CH₃	32.42±4.60	86.24±3.46
17g	CH₂CH₃	o-Pyridyl	Cl	OCH₂CH₃	16.74±2.53	81.96±0.77
17h	CH₂CH₃	o-Pyridyl	Cl	OCH₂CH₂CH₃	44.31±1.14	49.34±3.76
17i	CH₂CH₂CH₃	o-Pyridyl	Cl	OCH₂CH₃	31.25±1.75	36.68±3.20
17j	CH₂CH₂CH₃	o-Pyridyl	Cl	OCH₂CH₂CH₃	33.15±2.35	44.55±3.87
17k	CH₂CH₃	p-Pyridyl	Cl	OCH₂CH₃	9.90±3.85	51.73±4.48
17l	CH₂CH₃	p-Pyridyl	Cl	Ph	17.54±5.00	19.83±3.00
17m	H	p-Pyridyl	H	OCH₂CH₃	23.28±1.84	65.97±1.95
17n	H	p-Pyridyl	Cl	OCH₂CH₃	12.58±4.26	69.19±2.55
17o	H	p-Pyridyl	Cl	OCH₂CH₂CH₃	31.25±8.70	61.21±5.02
17p	CH₃	p-Pyridyl	Cl	OCH₂CH₂CH₃	26.60±8.06	50.77±4.57
17q	CH₂CH₂CH₃	p-Pyridyl	Cl	OCH₂CH₃	15.50±1.42	32.91±5.22
17r	CH₂CH₂CH₃	p-Pyridyl	Cl	OCH₂CH₂CH₃	16.28±3.82	27.60±4.80
5-Fu^b	—	11.84±1.90	14.13±1.34

新型含吡啶基3-硫醚-4-吲哚亚氨基-4H-1,2,4-三唑衍生物的设计、合成及体外生物活性评价

Novel 3-Thioether-4-indolimino-4H-1,2,4-triazole Derivatives Bearing Pyridyl Moiety: Design, Synthesis and Bioactivity Evaluation in vitro

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Compd.	Xoo		Compd.	Xoo
Compd.	50 μg/mL	100 μg/mL	Compd.	50 μg/mL	100 μg/mL
17a	36.96±0.66	60.69±5.54	17k	25.81±8.25	48.86±6.25
17b	43.01±6.57	66.43±9.54	17l	23.14±3.46	68.88±4.74
17c	28.81±4.92	63.33±1.10	17m	15.02±1.45	42.02±2.46
17d	27.18±4.25	57.75±2.06	17n	6.87±2.59	39.38±5.37
17e	44.17±3.61	67.01±2.93	17o	23.18±3.56	54.17±7.77
17f	26.02±9.02	59.91±8.83	17p	22.02±8.37	56.33±6.42
17g	27.55±1.31	65.17±2.47	17q	21.49±5.22	58.54±7.50
17h	35.83±4.81	71.27±1.58	17r	29.97±4.84	54.70±6.76
17i	21.49±5.29	53.96±2.83	BMT^b	28.02±4.49	64.38±0.86
17j	25.39±2.77	47.33±9.09	TDC^b	32.65±7.54	53.96±0.71

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