含1,3,4-噻二唑和吡唑的酰胺衍生物的合成和抗肿瘤活性研究

doi:10.6023/cjoc202102030

有机化学 ›› 2021, Vol. 41 ›› Issue (8): 3214-3222.DOI: 10.6023/cjoc202102030 上一篇下一篇

研究论文

含1,3,4-噻二唑和吡唑的酰胺衍生物的合成和抗肿瘤活性研究

马姣丽^a, 郭鹏虎^a, 李静^b, 廖新成^b, 程辉成^a^,^*()

a 广东石油化工学院化学学院广东茂名 525000
b 郑州大学化学与分子工程学院郑州 450052

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:
国家自然科学基金(22078072); 广东省基础与应用基础研究基金(2019A1515110346); 茂名市科技计划(2019401); 茂名市科技计划(2020581); 广东石油化工学院博士生启动基金(517152); 广东石油化工学院博士生启动基金(2019rc053); 广东石油化工学院青年创新人才培养基金(517136)

Synthesis and Antitumor Activity of Amide Derivatives Containing 1,3,4-Thiadiazole and Pyrazole Moieties

Jiaoli Ma^a, Penghu Guo^a, Jing Li^b, Xincheng Liao^b, Huicheng Cheng^a()

a College of Chemistry, Guangdong University of Petrochemical Technology, Maoming, Guangdong 525000
b College of Chemistry and Molecular Engineering, Zhengzhou University, Zhengzhou 450052

Received:2021-02-18 Revised:2021-03-30 Published:2021-05-14
Contact: Huicheng Cheng
Supported by:
National Natural Science Foundation of China(22078072); Guangdong Basic and Applied Basic Research Foundation(2019A1515110346); Science and Technology Plan of Maoming(2019401); Science and Technology Plan of Maoming(2020581); Doctor Startup Project of Guangdong University of Petrochemical Technology(517152); Doctor Startup Project of Guangdong University of Petrochemical Technology(2019rc053); Young Creative Talents Training Project of Guangdong University of Petrochemical Technology(517136)

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摘要/Abstract

以苯乙酮和草酸二乙酯为原料, 设计并合成了一系列含有1,3,4-噻二唑和吡唑的新型酰胺衍生物A1~A26, 通过¹H NMR, ¹³C NMR, IR, ESI-MS和HRMS等多种手段对其结构进行了表征. 通过噻唑蓝(MTT)方法评估了这些化合物对人肝癌细胞(HepG2)和人胃癌细胞(MGC803)体外抗肿瘤活性的表现. 实验结果表明, 以5-氟尿嘧啶作为阳性对照药物(IC₅₀=0.0787 μmol/mL), 化合物A1 (IC₅₀=0.0695 μmol/mL), A2 (IC₅₀=0.0682 μmol/mL)和A3 (IC₅₀=0.0753 μmol/mL)对HepG2细胞表现出相似的抑制作用. 值得注意的是, 化合物A1对MGC803细胞表现出较强的抑制作用 (IC₅₀=0.0420 μmol/ mL), 远比阳性对照药物5-氟尿嘧啶(IC₅₀=0.0820 μmol/mL)优异.

关键词: 酰胺衍生物, 有机合成, 1,3,4-噻二唑, 吡唑, 抗肿瘤活性

In this work, a series of newly-synthesized amide derivatives (A1~A26) carrying 1,3,4-thiadiazole and pyrazole moieties were successfully designed and synthesized. In addition, their structures were characterized by multiple techniques including ¹H NMR, ¹³C NMR, IR, ESI-MS and HRMS. Furthermore, based on the antitumor results against human hepatocarcinoma cells (HepG2) and human gastric carcinoma cells (MGC803) via methyl thiazolyl tetrazolium (MTT) method, the in vitro cytotoxic activities of the compounds were evaluated, indicating that compounds A1 (IC₅₀=0.0695 μmol/mL), A2 (IC₅₀=0.0682 μmol/mL) and A3 (IC₅₀=0.0753 μmol/mL) exhibited similar inhibitory effect against HepG2 cells. More importantly, compound A1 displayed superior inhibition performance against MGC803 cells (IC₅₀=0.0420 μmol/mL) compared with that of 5-fluorouracil (IC₅₀=0.0820 μmol/mL).

Key words: amide derivatives, organic synthesis, 1,3,4-thiadiazole, pyrazole, antitumor activity

引用此文

马姣丽, 郭鹏虎, 李静, 廖新成, 程辉成. 含1,3,4-噻二唑和吡唑的酰胺衍生物的合成和抗肿瘤活性研究[J]. 有机化学, 2021, 41(8): 3214-3222.

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.

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Compd.	R¹	R²	R³	Inhibition rate/%		Compd.	R¹	R²	R³	Inhibition rate/%
Compd.	R¹	R²	R³	HepG2	MGC803	Compd.	R¹	R²	R³	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/%
Compd.	R¹	R²	R³	HepG2	MGC803	Compd.	R¹	R²	R³	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

Entry	Compd.	IC₅₀/(μmol•mL^–1)
1	A1	0.0420
2	A7	—
3	A10	—
4	A19	—
5	A23	—
6	A24	—
7	5-Fluorouracil	0.0820

含1,3,4-噻二唑和吡唑的酰胺衍生物的合成和抗肿瘤活性研究

Synthesis and Antitumor Activity of Amide Derivatives Containing 1,3,4-Thiadiazole and Pyrazole Moieties

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