Synthesis and Antitumor Activity Study of 2,3-Substituted Tetrahydro- β-carboline Fused Diketopiperazine Derivatives

doi:10.6023/cjoc202603026

Chinese Journal of Organic Chemistry ›› 2026, Vol. 46 ›› Issue (8): 3089-3103.DOI: 10.6023/cjoc202603026 Previous Articles Next Articles

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2,3-位四氢-β-咔啉并二酮哌嗪类化合物合成及抗肿瘤活性研究

杨苗^a, 赵银九^a, 龚燕川^b, 张洁^a^,^*(), 郭亮^a^,^*()

^a 石河子大学化学化工学院化工绿色过程兵团重点实验室新疆石河子 832003
^b 新疆华世丹药物研究有限责任公司乌鲁木齐 830011

收稿日期:2026-03-19 修回日期:2026-04-20 发布日期:2026-06-03
通讯作者: 张洁, 郭亮
基金资助:
兵团指导计划(2022ZD019); 兵团指导计划(2023ZD073); 兵团科技攻关(2023AB047); 新疆科技重大专项(2024A03004-4); 兵团面上项目(2025DA061); 新疆青年科学基金(2024D01B23)

Synthesis and Antitumor Activity Study of 2,3-Substituted Tetrahydro- β-carboline Fused Diketopiperazine Derivatives

Miao Yang^a, Yinjiu Zhao^a, Yanchuan Gong^b, Jie Zhang^a^,^*(), Liang Guo^a^,^*()

^a Key Laboratory for Green Processing of Chemical Engineering of Xinjiang Bingtuan, School of Chemistry and Chemical Engineering, Shihezi University, Shihezi, Xinjiang 832003
^b Xinjiang Huashidan Pharmaceutical Research Co. Ltd., Urumqi 830011

Received:2026-03-19 Revised:2026-04-20 Published:2026-06-03
Contact: Jie Zhang, Liang Guo
Supported by:
Corps Guidance Plan(2022ZD019); Corps Guidance Plan(2023ZD073); Corps Science and Technology Breakthrough(2023AB047); Xinjiang Major Science and Technology Projects(2024A03004-4); Corps General Projectst(2025DA061); Xinjiang Youth Science Foundation(2024D01B23)

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Abstract

A series of 30 tetrahydro-β-carboline fused diketopiperazine derivatives containing different substituents were synthesized using the principle of drug combination. Their antiproliferative activities were evaluated against three tumor cell lines (LLC, A-549, NCI-H1666) via methyl thiazolyl tetrazolium (MTT) assay. The results showed that most compounds exhibited moderate to good inhibitory activity against these three tumor cell lines, and the IC₅₀ values of most compounds were below 20 μmol/L. Among them, the target compounds showed good inhibitory activity against A549 cell line, especially (S)-2,7-bis(4-fluorobenzyl)-1,2,3,6,7,12-hexahydropyrazine-4)-perhydro-β-carboline-1,4-dione (6o) and (S)-7-(4-fluorobenzyl)- 2-hexyl-1,2,3,6,7,12-hexahydro-4H-pyrazino[1,2-a]tetrahydro-β-carboline-1,4-dione (6y) showed excellent inhibitory activity against A549 cell line, with IC₅₀ values below 10 μmol/L. Overall, compound 6o, (S)-2-(4-fluorobenzyl)-7-(4-trifluoromethyl- benzyl)-1,2,3,6,7,12-hexahydro-4H-pyrazino[1,2-a]tetrahydro-β-carboline-1,4-dione (6p), 6y, and (S)-2-hexyl-7-(4-trifluoro- methylbenzyl)-1,2,3,6,7,12-hexahydro- 4H-pyrazino[1,2-a]tetrahydro-β-carboline-1,4-dione (6z) exhibit good inhibitory activity against LLC, A549, and NCI-H1666 cell lines, with IC₅₀ values all below 20 μmol/L, indicating potential anti-tumor research value. The molecular docking results indicate that compounds 6o and 6p have good interactions with multiple amino acid residues of VEGFR-2 (PDB:4AGD). Meanwhile, the molecular dynamics simulation results indicate that the binding stability and conformational consistency between compound 6p and 4AGD can be maintained.

Key words: tetrahydro-β-carboline, diketopiperazine, antitumor, molecular docking, molecular dynamics simulation

Cite this article

Miao Yang, Yinjiu Zhao, Yanchuan Gong, Jie Zhang, Liang Guo. Synthesis and Antitumor Activity Study of 2,3-Substituted Tetrahydro- β-carboline Fused Diketopiperazine Derivatives[J]. Chinese Journal of Organic Chemistry, 2026, 46(8): 3089-3103.

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Compd.	(IC₅₀±SD)^a/(μmol•L^－1)
Compd.	LLC	A549	NCI-H1666
5a	>50	>50	>50
5b	>50	>50	>50
5c	21.5±0.9	16.8±0.7	21.8±0.8
5d	>50	>50	15.4±2.3
5e	>50	24.7±1.1	32.3±1.3
Cisplatin	5.4±0.7	17.8±0.5	8.6±0.3

Compd.	(IC₅₀±SD)^a/(μmol•L^－1)
Compd.	LLC	A549	NCI-H1666
5a	>50	>50	>50
5b	>50	>50	>50
5c	21.5±0.9	16.8±0.7	21.8±0.8
5d	>50	>50	15.4±2.3
5e	>50	24.7±1.1	32.3±1.3
Cisplatin	5.4±0.7	17.8±0.5	8.6±0.3

Compd.	(IC₅₀±SD)^a/(μmol•L^－1)
Compd.	LLC	A549	NCI-H1666
6b	>50	>50	>50
6c	23.6±0.6	21.3±0.5	17.2±0.2
6d	18.7±0.3	>50	>50
6e	21.2±0.4	15.2±0.6	19.8±07
6f	29.2±0.3	12.9±0.5	15.6±0.7
6g	>50	>50	>50
6h	47.0±0.3	>50	>50
6i	>50	>50	16.4±1.5
6j	22.2±0.5	36.2±0.3	44.4±0.6
6k	24.7±0.3	17.5±0.5	13.8±0.2
6l	>50	34.8±0.4	14.0±0.1
6m	12.4±0.3	23.3±0.2	11.4±0.4
6n	13.7±0.4	28.2±1.3	12.9±1.1
6o	12.1±0.6	8.4±0.3	17.2±1.7
6p	7.9±0.6	13.4±1.4	14.2±0.6
6q	>50	>50	>50
6r	30.7±0.6	27.4±1.3	17.1±2.6
6s	17.4±0.5	9.9±0.1	15.8±1.3
6t	9.7±0.9	18.9±1.4	12.3±0.3
6u	14.4±0.3	13.5±0.6	18.6±1.6
6v	>50	39.3±0.9	23.0±1.1
6w	>50	34.3±0.3	18.3±0.5
6x	>50	25.4±0.7	16.0±0.4
6y	12.8±0.6	5.2±0.1	11.6±0.3
6z	13.4±0.4	13.3±0.7	14.7±0.7
Cispyatin	5.4±0.7	17.8±0.5	8.6±0.3

Compd.	(IC₅₀±SD)^a/(μmol•L^－1)
Compd.	LLC	A549	NCI-H1666
6b	>50	>50	>50
6c	23.6±0.6	21.3±0.5	17.2±0.2
6d	18.7±0.3	>50	>50
6e	21.2±0.4	15.2±0.6	19.8±07
6f	29.2±0.3	12.9±0.5	15.6±0.7
6g	>50	>50	>50
6h	47.0±0.3	>50	>50
6i	>50	>50	16.4±1.5
6j	22.2±0.5	36.2±0.3	44.4±0.6
6k	24.7±0.3	17.5±0.5	13.8±0.2
6l	>50	34.8±0.4	14.0±0.1
6m	12.4±0.3	23.3±0.2	11.4±0.4
6n	13.7±0.4	28.2±1.3	12.9±1.1
6o	12.1±0.6	8.4±0.3	17.2±1.7
6p	7.9±0.6	13.4±1.4	14.2±0.6
6q	>50	>50	>50
6r	30.7±0.6	27.4±1.3	17.1±2.6
6s	17.4±0.5	9.9±0.1	15.8±1.3
6t	9.7±0.9	18.9±1.4	12.3±0.3
6u	14.4±0.3	13.5±0.6	18.6±1.6
6v	>50	39.3±0.9	23.0±1.1
6w	>50	34.3±0.3	18.3±0.5
6x	>50	25.4±0.7	16.0±0.4
6y	12.8±0.6	5.2±0.1	11.6±0.3
6z	13.4±0.4	13.3±0.7	14.7±0.7
Cispyatin	5.4±0.7	17.8±0.5	8.6±0.3

Compd.	Protein	Hydrophobic interaction	Hydrogen bond	π-Cation interaction
Sunitinib	4AGD	ASP-46、VAL-80、ALA-98、GLU-117、ILE-121、 VAL-131、VAL-148、ASP-228	LYS-100、 GLU-117	LYS-100
6o	4AGD	GLU-117、LEU-121、ILE-121、VAL-130、LEU-201、 ASP-210、ILE-226、LEU-231	ARG-209
6p	4AGD	ALA-113、LEU-121、ILE-124、LEU-201、ASP-210、LEU-231	GLU-110	HIS-208

2,3-位四氢-β-咔啉并二酮哌嗪类化合物合成及抗肿瘤活性研究

Synthesis and Antitumor Activity Study of 2,3-Substituted Tetrahydro- β-carboline Fused Diketopiperazine Derivatives

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