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
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,*()
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:
基金资助:
Yayun Qia, Jiamin Liua, Chenpeng Lia, Weinan Hua, Siyu Tanga, Lihui Shaoa, Zhenchao Wanga,b,*(), Guiping Ouyanga,b,c,*()
Received:
2020-08-31
Revised:
2020-11-06
Published:
2020-12-10
Contact:
Zhenchao Wang, Guiping Ouyang
About author:
Supported by:
文章分享
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).
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.
Compd. | Inhibitory activitya/% at 10 μmol/L | |||
---|---|---|---|---|
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-Fub | 47.43±1.39 | 39.47±3.43 | 37.01±2.12 | 29.61±5.62 |
Compd. | Inhibitory activitya/% at 10 μmol/L | |||
---|---|---|---|---|
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-Fub | 47.43±1.39 | 39.47±3.43 | 37.01±2.12 | 29.61±5.62 |
Compd. | IC50a/(μmol?L-1) | |||
---|---|---|---|---|
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-Fub | 6.29±1.12 | 11.84±1.90 | 15.47±4.23 | 18.06±4.61 |
Compd. | IC50a/(μmol?L-1) | |||
---|---|---|---|---|
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-Fub | 6.29±1.12 | 11.84±1.90 | 15.47±4.23 | 18.06±4.61 |
Compd. | R1 | R2 | R3 | R4 | IC50a/(μmol?L–1) | |
---|---|---|---|---|---|---|
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-Fub | — | 11.84±1.90 | 14.13±1.34 |
Compd. | R1 | R2 | R3 | R4 | IC50a/(μmol?L–1) | |
---|---|---|---|---|---|---|
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-Fub | — | 11.84±1.90 | 14.13±1.34 |
Compd. | Xoo | Compd. | Xoo | ||
---|---|---|---|---|---|
50 μg/mL | 100 μg/mL | 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 | BMTb | 28.02±4.49 | 64.38±0.86 |
17j | 25.39±2.77 | 47.33±9.09 | TDCb | 32.65±7.54 | 53.96±0.71 |
Compd. | Xoo | Compd. | Xoo | ||
---|---|---|---|---|---|
50 μg/mL | 100 μg/mL | 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 | BMTb | 28.02±4.49 | 64.38±0.86 |
17j | 25.39±2.77 | 47.33±9.09 | TDCb | 32.65±7.54 | 53.96±0.71 |
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