吡咯并[1,2-<i>a</i>]喹喔啉类抗肿瘤活性剂的绿色合成—

引用本文: 盛荟茹, 齐蕊, 沈超, 徐好, 沈佳斌, 章鹏飞. 吡咯并[1,2-a]喹喔啉类抗肿瘤活性剂的绿色合成——综合化学实验教学探究[J]. 大学化学, 2026, 41(7): 266-273. doi: 10.12461/PKU.DXHX202505015 shu

Citation: Huiru Sheng, Rui Qi, Chao Shen, Hao Xu, Jiabin Shen, Pengfei Zhang. Green synthesis of pyrrolo[1,2-a]quinoxaline derivatives as antineoplastic agents: a comprehensive chemistry laboratory teaching exploration[J]. University Chemistry, 2026, 41(7): 266-273. doi: 10.12461/PKU.DXHX202505015 shu

吡咯并[1,2-a]喹喔啉类抗肿瘤活性剂的绿色合成——综合化学实验教学探究

盛荟茹 ^1, ,
齐蕊 ^1, ,
沈超 ^1, ,
徐好 ^1, ,
沈佳斌 ^{1,
,} ,
章鹏飞 ^{2,
,}

1.
浙江树人学院生物与环境工程学院, 浙江省化学与生物基础实验教学示范中心, 浙江杭州 310015;
2.
杭州师范大学材料与化学化工学院, 浙江省化学实验教学示范中心, 浙江杭州 311121

通讯作者: 沈佳斌,Email:shenjiabinhznu@163.com; 章鹏飞,Email:pfzhang@hznu.edu.cn

基金项目:
浙江省自然科学基金(LQN25B060012)

国家自然科学基金(22302178)

摘要: 本实验选择具有抗肿瘤活性的吡咯并[1,2-a]喹喔啉类分子骨架为研究对象，以硝酸和盐酸为氯气前体，在可见光催化下，利用芳基环丙烷的开环和关环反应一步合成吡咯并[1,2-a]喹喔啉类抗肿瘤活性剂。本实验将有机化学基础知识和学科前沿热点相结合，有助于提升学生的综合素质和创新能力，适合作为化学专业高年级的“综合化学实验”课程。

关键词:

English

Green synthesis of pyrrolo[1,2-a]quinoxaline derivatives as antineoplastic agents: a comprehensive chemistry laboratory teaching exploration

Huiru Sheng ^1, ,
Rui Qi ^1, ,
Chao Shen ^1, ,
Hao Xu ^1, ,
Jiabin Shen ^{1,
,} ,
Pengfei Zhang ^{2,
,}

1.
Basic Chemistry and Biology Experiments Teaching Center of Zhejiang Province, College of Biology and Environmental Engineering, Zhejiang Shuren University, Hangzhou 310015, Zhejiang Province, China;
2.
Experimental Chemistry Teaching Center of Zhejiang Province, College of Materials, Chemistry and Chemical Engineering, Hangzhou Normal University, Hangzhou 311121, Zhejiang Province, China

Corresponding author: Jiabin Shen, ; Pengfei Zhang,

Received Date: 08 May 2025
Revised Date: 29 July 2025
Available Online: 30 September 2025

Abstract: This study focuses on the molecular framework of pyrrolo[1,2-a]quinoxaline, known for its antitumor activity. Utilizing nitric acid and hydrochloric acid as chlorine gas precursors, we achieved a one-step synthesis of pyrrolo[1,2-a]quinoxaline antitumor agents through visible-light-catalyzed ring-opening and ring-closing reactions of arylcyclopropanes. By integrating fundamental organic chemistry principles with cutting-edge research topics, this experiment effectively enhances students’ comprehensive skills and innovative capabilities, making it particularly suitable as an advanced “comprehensive chemistry experiment” course for chemistry majors.

Key words:

1. [1]
  Q. Liu, W. Wang, M. Liu, Asian J. Org. Chem. 2023, 12(8), e202300277.Q. Liu, W. Wang, M. Liu, Asian J. Org. Chem. 2023, 12(8), e202300277.
2. [2]
  丛文霞, 王莉, 于福强, 李纪兴. 有机化学, 2018, 38(11), 2866.
3. [3]
  G.W.H. Cheeseman, B. Tuck, J. Chem. Soc. 1965, 3678.G.W.H. Cheeseman, B. Tuck, J. Chem. Soc. 1965, 3678.
4. [4]
  J.K. Laha, S. Panday, P. Gupta, S.R. Seth, Green Chem. 2023, 25(1), 161.J.K. Laha, S. Panday, P. Gupta, S.R. Seth, Green Chem. 2023, 25(1), 161.
5. [5]
  Q.C. Mu, Y.X. Nie, X.F. Bai, J. Chen, L. Yang, Z. Xu, L. Li, C.G. Xia, L.W. Xu, Chem. Sci. 2019, 10(40), 9292.Q.C. Mu, Y.X. Nie, X.F. Bai, J. Chen, L. Yang, Z. Xu, L. Li, C.G. Xia, L.W. Xu, Chem. Sci. 2019, 10(40), 9292.
6. [6]
  Q. Gao, J.M. Lu, L. Yao, S. Wang, J. Ying, X.F. Wu, Org. Lett. 2021, 23(1), 178.Q. Gao, J.M. Lu, L. Yao, S. Wang, J. Ying, X.F. Wu, Org. Lett. 2021, 23(1), 178.
7. [7]
  Z. Huang, J. Li, H. Nan, W. Yang, J. Zheng, J. Org. Chem. 2024, 89(15), 10434.Z. Huang, J. Li, H. Nan, W. Yang, J. Zheng, J. Org. Chem. 2024, 89(15), 10434.
8. [8]
  唐雨榕, 时允仁, 徐溢, 秦波, 徐彦芹, 蔡云飞. 大学化学, 2024, 39(5), 296.
9. [9]
  J. Shen, Y. Yang, C. Chen, H. Xu, C. Shen, P. Zhang, Org. Chem. Front. 2024, 11(6), 1758.J. Shen, Y. Yang, C. Chen, H. Xu, C. Shen, P. Zhang, Org. Chem. Front. 2024, 11(6), 1758.
10. [10]
  邸士睿, 王帅, 刘鑫, 朱红平. 大学化学, 2024, 39(1), 278.
11. [11]
  卢爱党, 李林, 史绍洋, 姜艳军. 大学化学, 2022, 37(3), 2105032.

扫一扫看文章

计量

PDF下载量: 0
文章访问数: 12
HTML全文浏览量: 1

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142

吡咯并[1,2-a]喹喔啉类抗肿瘤活性剂的绿色合成——综合化学实验教学探究

通讯作者: 沈佳斌,Email:shenjiabinhznu@163.com; 章鹏飞,Email:pfzhang@hznu.edu.cn

English

Green synthesis of pyrrolo[1,2-a]quinoxaline derivatives as antineoplastic agents: a comprehensive chemistry laboratory teaching exploration

Corresponding author: Jiabin Shen, ; Pengfei Zhang,

CCS Chemistry：嵌段共聚物自组装成 “三明治”二维有机材料，实现纳米级压力传感功能

CCS Chemistry：颜徐州、鲍哲南：你的皮肤可能是一片SPMs

CCS Chemistry：工作高效不疲劳，只须让催化剂动起来

CCS Chemistry：静电组装导向聚合- 聚电解质纳米凝胶量化制备新策略

CCS Chemistry：金黄色葡萄球菌醛基脱氢酶是如何识别特异性底物的？

计量

通讯作者: 陈斌, bchen63@163.com

中国化学会秘书处

吡咯并[1,2-a]喹喔啉类抗肿瘤活性剂的绿色合成——综合化学实验教学探究

通讯作者: 沈佳斌,Email:shenjiabinhznu@163.com; 章鹏飞,Email:pfzhang@hznu.edu.cn

English

Green synthesis of pyrrolo[1,2-a]quinoxaline derivatives as antineoplastic agents: a comprehensive chemistry laboratory teaching exploration

Corresponding author: Jiabin Shen, ; Pengfei Zhang,

CCS Chemistry：嵌段共聚物自组装成 “三明治”二维有机材料，实现纳米级压力传感功能

CCS Chemistry：颜徐州、鲍哲南： 你的皮肤可能是一片SPMs

CCS Chemistry：工作高效不疲劳，只须让催化剂动起来

CCS Chemistry：静电组装导向聚合- 聚电解质纳米凝胶量化制备新策略

CCS Chemistry：金黄色葡萄球菌醛基脱氢酶是如何识别特异性底物的？

计量

文章相关

通讯作者: 陈斌, bchen63@163.com

中国化学会秘书处

CCS Chemistry：颜徐州、鲍哲南：你的皮肤可能是一片SPMs