有机化学 ›› 2022, Vol. 42 ›› Issue (1): 277-292.DOI: 10.6023/cjoc202106053 上一篇 下一篇
研究论文
陈睿嘉a, 周聪a, 逄锡文a, 刘佳君b, 顾玉诚c, 刘建文b, 李忠a,*()
收稿日期:
2021-06-29
修回日期:
2021-08-02
发布日期:
2021-09-02
通讯作者:
李忠
基金资助:
Ruijia Chena, Cong Zhoua, Xiwen Panga, Jiajun Liub, Yucheng Guc, Jianwen Liub, Zhong Lia()
Received:
2021-06-29
Revised:
2021-08-02
Published:
2021-09-02
Contact:
Zhong Li
Supported by:
文章分享
为了探索具有新型骨架的抗癌剂, 设计了一系列的以环丙烷限制构象的双酰胺类化合物. 大多数含有顺式环丙烷中心的外消旋体对四种肿瘤细胞系(MCF-7、BGC-823、HepG2和NCI-H460)具有良好的抑制活性. 其中, 消旋体顺式-N1-(2-甲基-4-(全氟丙-2-基)苯基)-N2-(4-苯氧基苄基)环丙烷-1,2-二羧酰胺(1-19)对MCF-7的IC50值为(8.38±0.67) mg•L–1, 显示出可进一步优化为抗癌先导物的潜力. 此外, 甾醇硫酸酯酶(steryl-sulfatase, STS)被PharmMapper预测为可能的靶标蛋白, 并由分子对接实验进行了验证.
陈睿嘉, 周聪, 逄锡文, 刘佳君, 顾玉诚, 刘建文, 李忠. 以环丙烷限制构象的新型双酰胺的设计、合成、抗癌活性及计算分析[J]. 有机化学, 2022, 42(1): 277-292.
Ruijia Chen, Cong Zhou, Xiwen Pang, Jiajun Liu, Yucheng Gu, Jianwen Liu, Zhong Li. Design, Synthesis, Anti-cancer Activities and Computational Analysis of Novel Diamides Conformationally Restricted by Cyclopropane[J]. Chinese Journal of Organic Chemistry, 2022, 42(1): 277-292.
Compd. | Structure (Relative stereochemistry) | Growth-inhibition (200 μg•mL–1) | |||
---|---|---|---|---|---|
MCF-7 | BGC-823 | HepG2 | NCI-H460 | ||
1-2 | | 83.46±3.64 | 54.78±1.16 | 48.13±1.69 | 97.31±0.18 |
1-31 | | 19.42±1.19 | –28.92±2.03 | 38.24±5.37 | 14.20±6.58 |
Compd. | Structure (Relative stereochemistry) | Growth-inhibition (200 μg•mL–1) | |||
---|---|---|---|---|---|
MCF-7 | BGC-823 | HepG2 | NCI-H460 | ||
1-2 | | 83.46±3.64 | 54.78±1.16 | 48.13±1.69 | 97.31±0.18 |
1-31 | | 19.42±1.19 | –28.92±2.03 | 38.24±5.37 | 14.20±6.58 |
Compd. | R1 | Growth-inhibition (200 μg•mL–1) | |||
---|---|---|---|---|---|
MCF-7 | BGC-823 | HepG2 | NCI-H460 | ||
1-1 | Methyl | 37.23±3.34 | 32.39±1.17 | 23.47±4.79 | 47.37±0.50 |
1-2 | Ethyl | 83.46±3.64 | 54.78±1.16 | 48.13±1.69 | 97.31±0.18 |
1-3 | tert-Butyl | 85.73±2.92 | 4.17±0.52 | 57.57±1.57 | 94.34±2.25 |
1-4 | Benzyl | 96.83±0.69 | 97.75±0.08 | 99.14±0.28 | 98.42±0.16 |
1-30 | Phenethyl | 90.96±0.28 | 91.19±0.99 | 93.00±8.44 | 97.46±0.16 |
Compd. | R1 | Growth-inhibition (200 μg•mL–1) | |||
---|---|---|---|---|---|
MCF-7 | BGC-823 | HepG2 | NCI-H460 | ||
1-1 | Methyl | 37.23±3.34 | 32.39±1.17 | 23.47±4.79 | 47.37±0.50 |
1-2 | Ethyl | 83.46±3.64 | 54.78±1.16 | 48.13±1.69 | 97.31±0.18 |
1-3 | tert-Butyl | 85.73±2.92 | 4.17±0.52 | 57.57±1.57 | 94.34±2.25 |
1-4 | Benzyl | 96.83±0.69 | 97.75±0.08 | 99.14±0.28 | 98.42±0.16 |
1-30 | Phenethyl | 90.96±0.28 | 91.19±0.99 | 93.00±8.44 | 97.46±0.16 |
Compd. | R1 | IC50/(μg•mL–1) | |||
---|---|---|---|---|---|
MCF-7 | BGC-823 | HepG2 | NCI-H460 | ||
1-1 | Methyl | >200 | >200 | >200 | >200 |
1-2 | Ethyl | 33.81±2.06 | >200 | >200 | 29.80±2.91 |
1-3 | tert-Butyl | 29.27±5.83 | >200 | >200 | 38.38±1.40 |
1-4 | Benzyl | 40.79±2.18 | 50.90±0.99 | 26.09±2.97 | 26.78±2.78 |
1-5 | 4-Methylbenzyl | 32.29±1.7 | 21.25±3.03 | 10.44±1.60 | 20.38±1.21 |
1-6 | 3-Methylbenzyl | 40.35±5.19 | 35.50±3.97 | 35.01±1.54 | 30.59±1.18 |
1-7 | 2-Methylbenzyl | 33.80±1.72 | 25.42±2.29 | 23.20±1.07 | 21.60±1.60 |
1-8 | 4-Chlorobenzyl | 36.89±2.29 | 19.47±5.37 | 17.65±1.24 | 10.06±1.82 |
1-9 | 3-Chlorobenzyl | 36.80±4.39 | 30.58±2.65 | 28.62±0.81 | 22.48±0.71 |
1-10 | 2-Chlorobenzyl | 80.47±6.93 | 31.75±4.74 | 22.75±0.84 | 21.61±1.30 |
1-11 | 4-Fluorobenzyl | 67.45±2.43 | 29.55±2.70 | 27.07±1.05 | 25.27±2.85 |
1-12 | 4-Bromobenzyl | 17.65±0.99 | 28.29±2.54 | 21.17±0.81 | 21.01±1.25 |
1-13 | 4-Iodobenzyl | 27.57±6.26 | 26.24±2.70 | 26.29±1.43 | 26.15±1.36 |
1-14 | 4-Methoxybenzyl | 20.78±1.38 | 24.51±2.57 | 24.14±1.23 | 25.17±1.84 |
1-15 | 4-Difluoromethoxybenzyl | 75.61±14.80 | 50.03±2.97 | 39.52±6.27 | 56.80±10.58 |
1-16 | 4-tert-Butylbenzyl | >200 | 92.61±16.39 | >200 | 95.35±17.62 |
1-17 | 4-Cyanobenzyl | 47.75±9.06 | 42.49±4.12 | 37.92±2.94 | 30.26±3.15 |
1-18 | 4-Trifluoromethylbenzyl | 25.66±1.11 | 21.39±1.11 | 21.23±1.99 | 15.12±1.43 |
1-19 | (4-Phenoxyphenyl)methyl | 8.38±0.67 | 22.67±0.80 | 19.30±1.10 | 20.49±1.32 |
1-20 | 4-Phenylbenzyl | 25.88±2.95 | 24.97±1.27 | 27.06±3.07 | 22.94±1.15 |
1-21 | 2,4-Difluorobenzyl | 40.84±1.24 | 51.29±1.09 | 23.52±2.50 | 28.35±2.28 |
1-22 | 2,6-Dichlorobenzyl | >200 | >200 | 19.74±0.79 | 39.89±9.27 |
1-23 | 3,4,5-Trimethoxybenzyl | 19.16±3.01 | 34.39±3.52 | 27.22±2.61 | 20.39±1.41 |
1-24 | (Tetrahydrofuran-3-yl)methyl | 153.9±20.2 | 50.30±6.65 | 46.88±5.39 | 56.51±11.21 |
1-25 | (6-Chloropyridine-3-yl)methyl | 27.12±0.92 | 32.39±3.46 | 34.15±0.94 | 29.36±1.79 |
1-26 | (2-Chlorothiazole-5-yl)methyl | >200 | >200 | >200 | >200 |
1-27 | Furan-2-ylmethyl | 25.8±1.32 | 32.39±4.40 | 15.42±4.40 | 27.03±2.49 |
1-28 | Thiophene-3-ylmethyl | 83.43±4.37 | >200 | >200 | >200 |
1-29 | Naphthalene-1-ylmethyl | 32.53±2.82 | 22.91±1.20 | 23.55±1.97 | 20.52±0.98 |
1-30 | Phenethyl | 59.05±3.60 | 53.12±1.16 | 26.76±1.18 | 30.37±2.36 |
5-Fu | — | 8.23±1.33 | 10.31±1.40 | 7.09±1.61 | 2.26±0.80 |
Compd. | R1 | IC50/(μg•mL–1) | |||
---|---|---|---|---|---|
MCF-7 | BGC-823 | HepG2 | NCI-H460 | ||
1-1 | Methyl | >200 | >200 | >200 | >200 |
1-2 | Ethyl | 33.81±2.06 | >200 | >200 | 29.80±2.91 |
1-3 | tert-Butyl | 29.27±5.83 | >200 | >200 | 38.38±1.40 |
1-4 | Benzyl | 40.79±2.18 | 50.90±0.99 | 26.09±2.97 | 26.78±2.78 |
1-5 | 4-Methylbenzyl | 32.29±1.7 | 21.25±3.03 | 10.44±1.60 | 20.38±1.21 |
1-6 | 3-Methylbenzyl | 40.35±5.19 | 35.50±3.97 | 35.01±1.54 | 30.59±1.18 |
1-7 | 2-Methylbenzyl | 33.80±1.72 | 25.42±2.29 | 23.20±1.07 | 21.60±1.60 |
1-8 | 4-Chlorobenzyl | 36.89±2.29 | 19.47±5.37 | 17.65±1.24 | 10.06±1.82 |
1-9 | 3-Chlorobenzyl | 36.80±4.39 | 30.58±2.65 | 28.62±0.81 | 22.48±0.71 |
1-10 | 2-Chlorobenzyl | 80.47±6.93 | 31.75±4.74 | 22.75±0.84 | 21.61±1.30 |
1-11 | 4-Fluorobenzyl | 67.45±2.43 | 29.55±2.70 | 27.07±1.05 | 25.27±2.85 |
1-12 | 4-Bromobenzyl | 17.65±0.99 | 28.29±2.54 | 21.17±0.81 | 21.01±1.25 |
1-13 | 4-Iodobenzyl | 27.57±6.26 | 26.24±2.70 | 26.29±1.43 | 26.15±1.36 |
1-14 | 4-Methoxybenzyl | 20.78±1.38 | 24.51±2.57 | 24.14±1.23 | 25.17±1.84 |
1-15 | 4-Difluoromethoxybenzyl | 75.61±14.80 | 50.03±2.97 | 39.52±6.27 | 56.80±10.58 |
1-16 | 4-tert-Butylbenzyl | >200 | 92.61±16.39 | >200 | 95.35±17.62 |
1-17 | 4-Cyanobenzyl | 47.75±9.06 | 42.49±4.12 | 37.92±2.94 | 30.26±3.15 |
1-18 | 4-Trifluoromethylbenzyl | 25.66±1.11 | 21.39±1.11 | 21.23±1.99 | 15.12±1.43 |
1-19 | (4-Phenoxyphenyl)methyl | 8.38±0.67 | 22.67±0.80 | 19.30±1.10 | 20.49±1.32 |
1-20 | 4-Phenylbenzyl | 25.88±2.95 | 24.97±1.27 | 27.06±3.07 | 22.94±1.15 |
1-21 | 2,4-Difluorobenzyl | 40.84±1.24 | 51.29±1.09 | 23.52±2.50 | 28.35±2.28 |
1-22 | 2,6-Dichlorobenzyl | >200 | >200 | 19.74±0.79 | 39.89±9.27 |
1-23 | 3,4,5-Trimethoxybenzyl | 19.16±3.01 | 34.39±3.52 | 27.22±2.61 | 20.39±1.41 |
1-24 | (Tetrahydrofuran-3-yl)methyl | 153.9±20.2 | 50.30±6.65 | 46.88±5.39 | 56.51±11.21 |
1-25 | (6-Chloropyridine-3-yl)methyl | 27.12±0.92 | 32.39±3.46 | 34.15±0.94 | 29.36±1.79 |
1-26 | (2-Chlorothiazole-5-yl)methyl | >200 | >200 | >200 | >200 |
1-27 | Furan-2-ylmethyl | 25.8±1.32 | 32.39±4.40 | 15.42±4.40 | 27.03±2.49 |
1-28 | Thiophene-3-ylmethyl | 83.43±4.37 | >200 | >200 | >200 |
1-29 | Naphthalene-1-ylmethyl | 32.53±2.82 | 22.91±1.20 | 23.55±1.97 | 20.52±0.98 |
1-30 | Phenethyl | 59.05±3.60 | 53.12±1.16 | 26.76±1.18 | 30.37±2.36 |
5-Fu | — | 8.23±1.33 | 10.31±1.40 | 7.09±1.61 | 2.26±0.80 |
Compd. | Pharma model (PDB ID) | Normalized fit score |
---|---|---|
1-12 | 1p49 | 0.996 |
2vwu | 0.996 | |
2brb | 0.988 | |
2pg2 | 0.980 | |
1juj | 0.963 | |
2g01 | 0.956 | |
2ity | 0.935 | |
2ovm | 0.929 | |
1o4i | 0.906 | |
1-14 | 1p49 | 0.996 |
2vwu | 0.995 | |
2pg2 | 0.979 | |
1juj | 0.977 | |
1ya8 | 0.957 | |
2ovm | 0.944 | |
2ity | 0.925 | |
1-19 | 1p49 | 0.996 |
2vwu | 0.994 | |
2pg2 | 0.980 | |
1juj | 0.971 | |
1ya8 | 0.971 | |
2g01 | 0.946 | |
2ity | 0.928 | |
1o4i | 0.903 | |
1-23 | 1p49 | 0.995 |
2vwu | 0.993 | |
2c3i | 0.987 | |
2pg2 | 0.979 | |
1ya8 | 0.972 | |
1juj | 0.967 | |
2ocf | 0.942 | |
2ity | 0.930 |
Compd. | Pharma model (PDB ID) | Normalized fit score |
---|---|---|
1-12 | 1p49 | 0.996 |
2vwu | 0.996 | |
2brb | 0.988 | |
2pg2 | 0.980 | |
1juj | 0.963 | |
2g01 | 0.956 | |
2ity | 0.935 | |
2ovm | 0.929 | |
1o4i | 0.906 | |
1-14 | 1p49 | 0.996 |
2vwu | 0.995 | |
2pg2 | 0.979 | |
1juj | 0.977 | |
1ya8 | 0.957 | |
2ovm | 0.944 | |
2ity | 0.925 | |
1-19 | 1p49 | 0.996 |
2vwu | 0.994 | |
2pg2 | 0.980 | |
1juj | 0.971 | |
1ya8 | 0.971 | |
2g01 | 0.946 | |
2ity | 0.928 | |
1o4i | 0.903 | |
1-23 | 1p49 | 0.995 |
2vwu | 0.993 | |
2c3i | 0.987 | |
2pg2 | 0.979 | |
1ya8 | 0.972 | |
1juj | 0.967 | |
2ocf | 0.942 | |
2ity | 0.930 |
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