Design, Synthesis and Antitumor Activity of Novel Imide-β-carboline

doi:10.6023/cjoc202504013

Chinese Journal of Organic Chemistry ›› 2025, Vol. 45 ›› Issue (12): 4362-4374.DOI: 10.6023/cjoc202504013 Previous Articles Next Articles

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新型酰亚胺-β-咔啉的设计、合成及其抗肿瘤活性研究

邱东平, 王兆旭, 张洁^*(), 郭亮^*()

石河子大学化学化工学院化工绿色过程兵团重点实验室化工绿色过程兵团重点实验室新疆石河子 832003

收稿日期:2025-04-12 修回日期:2025-06-27 发布日期:2025-08-18
通讯作者: 张洁, 郭亮
基金资助:
国家自然科学基金(22067017); 新疆生产建设兵团指导计划(2022ZD019); 新疆生产建设兵团指导计划(2023ZD073); 新疆生产建设兵团科技攻关(2023AB047); 新疆生产建设兵团科技攻关(2023AB054); 新疆科技重大专项(2022A02006-5)

Design, Synthesis and Antitumor Activity of Novel Imide-β-carboline

Dongping Qiu, Zhaoxu Wang, Jie Zhang^*(), Liang Guo^*()

Key Laboratory for Green Processing of Chemical Engineering of Xinjiang Bingtuan, School of Chemistry and Chemical Engineering, Shihezi University, Shihezi, Xinjiang 832003

Received:2025-04-12 Revised:2025-06-27 Published:2025-08-18
Contact: Jie Zhang, Liang Guo
Supported by:
National Natural Science Foundation of China(22067017); Guidance Plan Project of Xinjiang Production and Construction Corps(2022ZD019); Guidance Plan Project of Xinjiang Production and Construction Corps(2023ZD073); Science and Technology Research Projects of Xinjiang Production and Construction Corps(2023AB047); Science and Technology Research Projects of Xinjiang Production and Construction Corps(2023AB054); Xinjiang Science and Technology Major Project(2022A02006-5)

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Abstract

In order to find novel compounds with superior antitumor activity, a series of 6-(N-imide)-β-carboline derivatives with diverse substituents, totaling 30 compounds, were designed and synthesized. The inhibitory effects of these compounds on five cancer cell lines, namely lung cancer (A549), gastric cancer (BGC-823), colon cancer (CT-26), liver cancer (Bel-7402), and breast cancer (MCF-7), were evaluated using methyl thiazolyl tetrazolium (MTT) assay. The experimental results indicated that most target compounds exhibit better antitumor activity against the tested cell lines, with half-maximal inhibitory concentrations (IC₅₀) values below 20 μmol/L. Moreover, the series of compounds showed better inhibitory activity against the A549 and Bel-7402 cell lines. In particular, compounds 5j, 5p, and 5ac exhibited excellent inhibitory activity against tumor cells, demonstrating potential value for antitumor research. Specifically, compounds 5j and 5p exhibited excellent inhibitory activity against the A549, BGC-823, and Bel-7402 cell lines, while compound 5ac showed excellent inhibitory activity against the A549, Bel-7402, and MCF-7 cell lines, all with IC₅₀ values less than 10 μmol/L. The molecular docking results indicate that compound 5ac exhibits favorable binding interactions with multiple amino acid residues of vascular endothelial growth factor receptor-2 (VEGFR-2).

Key words: β-carboline, imide, antitumor, molecular docking

Cite this article

Dongping Qiu, Zhaoxu Wang, Jie Zhang, Liang Guo. Design, Synthesis and Antitumor Activity of Novel Imide-β-carboline[J]. Chinese Journal of Organic Chemistry, 2025, 45(12): 4362-4374.

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Compd.	R⁹	(IC₅₀±SD)^a/(μmol•L^－1)
Compd.	R⁹	A549	BGC-823	CT-26	Bel-7402	MCF-7
4e	C₂H₅	31.8±1.5	22.1±1.1	43.2±2.1	18.8±0.8	34.2±1.6
4f	n-C₄H₉	>50	43.9±2.2	35.2±1.6	20.3±0.9	32.7±1.5
4g	CH₂C₆H₅	37.9±2.8	>50	>50	46.6±4.4	23.2±1.1
4h	CH₂C₆H₄(p-F)	16.8±0.8	27.3±1.2	36.2±1.8	20.8±0.9	15.2±0.7
Cisplatin		18.3±0.6	10.6±0.4	5.7±0.1	14.2±0.7	10.6±0.4

Compd.	R⁹	(IC₅₀±SD)^a/(μmol•L^－1)
Compd.	R⁹	A549	BGC-823	CT-26	Bel-7402	MCF-7
4e	C₂H₅	31.8±1.5	22.1±1.1	43.2±2.1	18.8±0.8	34.2±1.6
4f	n-C₄H₉	>50	43.9±2.2	35.2±1.6	20.3±0.9	32.7±1.5
4g	CH₂C₆H₅	37.9±2.8	>50	>50	46.6±4.4	23.2±1.1
4h	CH₂C₆H₄(p-F)	16.8±0.8	27.3±1.2	36.2±1.8	20.8±0.9	15.2±0.7
Cisplatin		18.3±0.6	10.6±0.4	5.7±0.1	14.2±0.7	10.6±0.4

Compd.	R¹	R⁵	R⁹	(IC₅₀±SD)^a/(μmol•L^－1)
Compd.	R¹	R⁵	R⁹	A549	BGC-823	CT-26	Bel-7402	MCF-7
5a	H	Cl	CH₃	13.1±0.6	7.1±0.3	9.9±0.5	12.6±0.6	16.1±0.8
5b	Cl	Cl	CH₃	17.3±0.8	13.3±0.6	9.6±0.5	13.4±0.6	9.9±0.5
5c	H	Cl	CH₂C₆F₅	14.5±0.7	8.3±0.4	11.6±0.5	9.8±0.4	17.4±0.8
5d	Cl	Cl	CH₂C₆F₅	12.4±0.6	13.8±0.6	8.4±0.4	10.3±0.4	11.7±0.5
5e	H	H	H	25.3±1.2	30.6±1.5	19.4±0.9	27.7±1.2	36.6±1.8
5f	H	H	CH₃	13.3±0.6	9.6±0.4	11.7±0.5	10.4±0.5	18.9±0.8
5g	H	H	C₂H₅	12.4±0.6	12.5±0.6	12.1±0.6	13.8±0.6	13.1±0.6
5h	H	H	n-C₄H₉	14.2±0.6	17.3±0.8	18.2±0.9	13.1±0.6	26.9±1.3
5i	H	H	CH₂C₆H₅	9.9±0.4	11.6±0.5	15.1±0.7	28.7±1.3	13.2±0.6
5j	H	H	CH₂C₆H₄(p-F)	8.1±0.4	8.9±0.4	12.7±0.6	7.6±0.3	11.3±0.5
5k	H	H	CH₂C₆F₅	14.1±0.6	9.7±0.5	11.9±0.5	13.5±0.7	7.9±0.4
5l	Cl	H	CH₃	21.4±1.0	11.6±0.5	12.9±0.6	16.2±0.8	11.9±0.5
5m	Cl	H	C₂H₅	12.2±0.5	22.6±1.1	28.8±1.4	10.8±0.5	26.1±1.1
5n	Br	H	C₂H₅	13.9±0.6	11.7±0.5	15.7±0.7	11.3±0.5	9.7±0.4
5o	CH₃	H	C₂H₅	22.1±1.1	21.3±1.1	37.4±1.8	12.8±0.6	24.7±1.1
5p	Cl	H	CH₂C₆F₅	6.5±0.1	9.5±0.4	12.4±0.6	7.8±0.3	11.1±0.5
5q	Br	H	CH₂C₆F₅	13.4±0.7	14.2±0.7	11.6±0.5	9.7±0.4	8.8±0.4
5r	CH₃	H	CH₂C₆F₅	23.5±1.1	15.8±0.6	20.3±1.0	12.9±0.6	14.7±0.7
Cisplatin				18.3±0.6	10.6±0.4	5.7±0.1	14.2±0.7	10.6±0.4

Compd.	R¹	R⁵	R⁹	(IC₅₀±SD)^a/(μmol•L^－1)
Compd.	R¹	R⁵	R⁹	A549	BGC-823	CT-26	Bel-7402	MCF-7
5a	H	Cl	CH₃	13.1±0.6	7.1±0.3	9.9±0.5	12.6±0.6	16.1±0.8
5b	Cl	Cl	CH₃	17.3±0.8	13.3±0.6	9.6±0.5	13.4±0.6	9.9±0.5
5c	H	Cl	CH₂C₆F₅	14.5±0.7	8.3±0.4	11.6±0.5	9.8±0.4	17.4±0.8
5d	Cl	Cl	CH₂C₆F₅	12.4±0.6	13.8±0.6	8.4±0.4	10.3±0.4	11.7±0.5
5e	H	H	H	25.3±1.2	30.6±1.5	19.4±0.9	27.7±1.2	36.6±1.8
5f	H	H	CH₃	13.3±0.6	9.6±0.4	11.7±0.5	10.4±0.5	18.9±0.8
5g	H	H	C₂H₅	12.4±0.6	12.5±0.6	12.1±0.6	13.8±0.6	13.1±0.6
5h	H	H	n-C₄H₉	14.2±0.6	17.3±0.8	18.2±0.9	13.1±0.6	26.9±1.3
5i	H	H	CH₂C₆H₅	9.9±0.4	11.6±0.5	15.1±0.7	28.7±1.3	13.2±0.6
5j	H	H	CH₂C₆H₄(p-F)	8.1±0.4	8.9±0.4	12.7±0.6	7.6±0.3	11.3±0.5
5k	H	H	CH₂C₆F₅	14.1±0.6	9.7±0.5	11.9±0.5	13.5±0.7	7.9±0.4
5l	Cl	H	CH₃	21.4±1.0	11.6±0.5	12.9±0.6	16.2±0.8	11.9±0.5
5m	Cl	H	C₂H₅	12.2±0.5	22.6±1.1	28.8±1.4	10.8±0.5	26.1±1.1
5n	Br	H	C₂H₅	13.9±0.6	11.7±0.5	15.7±0.7	11.3±0.5	9.7±0.4
5o	CH₃	H	C₂H₅	22.1±1.1	21.3±1.1	37.4±1.8	12.8±0.6	24.7±1.1
5p	Cl	H	CH₂C₆F₅	6.5±0.1	9.5±0.4	12.4±0.6	7.8±0.3	11.1±0.5
5q	Br	H	CH₂C₆F₅	13.4±0.7	14.2±0.7	11.6±0.5	9.7±0.4	8.8±0.4
5r	CH₃	H	CH₂C₆F₅	23.5±1.1	15.8±0.6	20.3±1.0	12.9±0.6	14.7±0.7
Cisplatin				18.3±0.6	10.6±0.4	5.7±0.1	14.2±0.7	10.6±0.4

Compd.	R⁹	(IC₅₀±SD)^a/(μmol•L^－1)
Compd.	R⁹	A549	BGC-823	CT-26	Bel-7402	MCF-7
5s	H	29.6±1.4	43.7±2.1	24.2±1.2	23.3±1.1	32.7±1.6
5t	CH₃	23.4±1.2	16.7±0.8	18.5±0.9	17.1±0.8	18.9±0.8
5u	C₂H₅	25.4±1.2	11.3±0.5	17.1±0.8	16.7±0.8	24.2±1.2
5v	n-C₄H₉	21.7±0.9	17.2±0.8	18.7±0.8	9.1±0.4	22.9±1.1
5w	CH₂C₆H₅	19.2±0.9	12.9±0.6	11.2±0.5	10.5±0.5	20.1±0.9
5x	CH₂C₆H₄(p-F)	16.6±0.6	15.1±0.7	33.7±1.6	8.3±0.4	14.9±0.6
5y	CH₂C₆F₅	18.5±0.8	16.6±0.8	18.7±0.9	24.5±1.2	21.4±1.0
Cisplatin		18.3±0.6	10.6±0.4	5.7±0.1	14.2±0.7	10.6±0.4

新型酰亚胺-β-咔啉的设计、合成及其抗肿瘤活性研究

Design, Synthesis and Antitumor Activity of Novel Imide-β-carboline

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