Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (8): 3214-3222.DOI: 10.6023/cjoc202102030 Previous Articles Next Articles
ARTICLES
马姣丽a, 郭鹏虎a, 李静b, 廖新成b, 程辉成a,*()
收稿日期:
2021-02-18
修回日期:
2021-03-30
发布日期:
2021-05-14
通讯作者:
程辉成
基金资助:
Jiaoli Maa, Penghu Guoa, Jing Lib, Xincheng Liaob, Huicheng Chenga()
Received:
2021-02-18
Revised:
2021-03-30
Published:
2021-05-14
Contact:
Huicheng Cheng
Supported by:
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Jiaoli Ma, Penghu Guo, Jing Li, Xincheng Liao, Huicheng Cheng. Synthesis and Antitumor Activity of Amide Derivatives Containing 1,3,4-Thiadiazole and Pyrazole Moieties[J]. Chinese Journal of Organic Chemistry, 2021, 41(8): 3214-3222.
Compd. | R1 | R2 | R3 | Inhibition rate/% | Compd. | R1 | R2 | R3 | Inhibition rate/% | ||
---|---|---|---|---|---|---|---|---|---|---|---|
HepG2 | MGC803 | HepG2 | MGC803 | ||||||||
A1 | H | H | C6H5CH2 | 50.6 | 54.2 | A14 | p-OMe | CH3 | C6H5CH2 | 54.8 | 30.8 |
A2 | H | H | 2-CH3C6H4CH2 | 73.1 | 3.5 | A15 | p-OMe | CH3 | 2-CH3C6H4CH2 | 53.2 | 31.8 |
A3 | H | H | 3-CH3C6H4CH2 | 66.2 | 15.3 | A16 | p-OMe | CH3 | 3-CH3C6H4CH2 | 61.7 | 12.6 |
A4 | H | H | 4-CH3C6H4CH2 | 25.3 | 36.1 | A17 | p-OMe | CH3 | 4-CH3C6H4CH2 | 2.8 | 47.4 |
A5 | H | H | 4-CH3OC6H4CH2 | 5.7 | 26.1 | A18 | p-OMe | CH3 | 4-CH3OC6H4CH2 | 28.3 | –9.0 |
A6 | H | H | CH2CO2Et | 35.8 | 42.6 | A19 | p-OMe | CH3 | CH2CO2Et | 36.8 | 53.7 |
A7 | H | H | 4-NO2C6H4CH2 | 18.4 | 57.5 | A20 | p-OMe | CH3 | 4-NO2C6H4CH2 | 37.6 | 49.3 |
A8 | H | H | 4-NCC6H4CH2 | 16.1 | 45.9 | A21 | p-OMe | CH3 | 4-NCC6H4CH2 | 24.9 | 46.6 |
A9 | H | CH3 | C6H5CH2 | 54.4 | 26.0 | A22 | 3,4-Cl2 | CH3 | C6H5CH2 | 17.0 | 45.8 |
A10 | H | CH3 | 2-CH3C6H4CH2 | 42.9 | 50.3 | A23 | 3,4-Cl2 | CH3 | 2-CH3C6H4CH2 | 22.7 | 59.3 |
A11 | H | CH3 | 4-CH3C6H4CH2 | 59.8 | 44.8 | A24 | 3,4-Cl2 | CH3 | 3-CH3C6H4CH2 | 12.3 | 54.8 |
A12 | H | CH3 | 4-CH3OC6H4CH2 | 34.3 | 40.1 | A25 | 3,4-Cl2 | CH3 | 4-CH3OC6H4CH2 | 50.3 | 35.2 |
A13 | H | CH3 | 4-NO2C6H4CH2 | 60.6 | 27.7 | A26 | 3,4-Cl2 | CH3 | 4-NO2C6H4CH | 55.9 | 45.8 |
Compd. | R1 | R2 | R3 | Inhibition rate/% | Compd. | R1 | R2 | R3 | Inhibition rate/% | ||
---|---|---|---|---|---|---|---|---|---|---|---|
HepG2 | MGC803 | HepG2 | MGC803 | ||||||||
A1 | H | H | C6H5CH2 | 50.6 | 54.2 | A14 | p-OMe | CH3 | C6H5CH2 | 54.8 | 30.8 |
A2 | H | H | 2-CH3C6H4CH2 | 73.1 | 3.5 | A15 | p-OMe | CH3 | 2-CH3C6H4CH2 | 53.2 | 31.8 |
A3 | H | H | 3-CH3C6H4CH2 | 66.2 | 15.3 | A16 | p-OMe | CH3 | 3-CH3C6H4CH2 | 61.7 | 12.6 |
A4 | H | H | 4-CH3C6H4CH2 | 25.3 | 36.1 | A17 | p-OMe | CH3 | 4-CH3C6H4CH2 | 2.8 | 47.4 |
A5 | H | H | 4-CH3OC6H4CH2 | 5.7 | 26.1 | A18 | p-OMe | CH3 | 4-CH3OC6H4CH2 | 28.3 | –9.0 |
A6 | H | H | CH2CO2Et | 35.8 | 42.6 | A19 | p-OMe | CH3 | CH2CO2Et | 36.8 | 53.7 |
A7 | H | H | 4-NO2C6H4CH2 | 18.4 | 57.5 | A20 | p-OMe | CH3 | 4-NO2C6H4CH2 | 37.6 | 49.3 |
A8 | H | H | 4-NCC6H4CH2 | 16.1 | 45.9 | A21 | p-OMe | CH3 | 4-NCC6H4CH2 | 24.9 | 46.6 |
A9 | H | CH3 | C6H5CH2 | 54.4 | 26.0 | A22 | 3,4-Cl2 | CH3 | C6H5CH2 | 17.0 | 45.8 |
A10 | H | CH3 | 2-CH3C6H4CH2 | 42.9 | 50.3 | A23 | 3,4-Cl2 | CH3 | 2-CH3C6H4CH2 | 22.7 | 59.3 |
A11 | H | CH3 | 4-CH3C6H4CH2 | 59.8 | 44.8 | A24 | 3,4-Cl2 | CH3 | 3-CH3C6H4CH2 | 12.3 | 54.8 |
A12 | H | CH3 | 4-CH3OC6H4CH2 | 34.3 | 40.1 | A25 | 3,4-Cl2 | CH3 | 4-CH3OC6H4CH2 | 50.3 | 35.2 |
A13 | H | CH3 | 4-NO2C6H4CH2 | 60.6 | 27.7 | A26 | 3,4-Cl2 | CH3 | 4-NO2C6H4CH | 55.9 | 45.8 |
Entry | Compd. | IC50/(μmol•mL–1) |
---|---|---|
1 | A1 | 0.0695 |
2 | A2 | 0.0682 |
3 | A3 | 0.0753 |
4 | A9 | 3.0229 |
5 | A11 | — |
6 | A13 | 0.6020 |
7 | A14 | — |
8 | A15 | — |
9 | A16 | 0.4666 |
10 | A25 | 0.2553 |
11 | A26 | — |
12 | 5-Fluorouracil | 0.0787 |
Entry | Compd. | IC50/(μmol•mL–1) |
---|---|---|
1 | A1 | 0.0695 |
2 | A2 | 0.0682 |
3 | A3 | 0.0753 |
4 | A9 | 3.0229 |
5 | A11 | — |
6 | A13 | 0.6020 |
7 | A14 | — |
8 | A15 | — |
9 | A16 | 0.4666 |
10 | A25 | 0.2553 |
11 | A26 | — |
12 | 5-Fluorouracil | 0.0787 |
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