大学化学 >> 2024, Vol. 39 >> Issue (3): 316-326.doi: 10.3866/PKU.DXHX202309091

化学实验 上一篇    下一篇

磺酰腙的高效快速合成及其抗菌性能初探——推荐一个医学本科院校化学创新实验

唐敬杰2, 谢露影2, 刘嘉昱3, 石尚玉2, 孙欣雨2, 林家阳2, 杨琦堃2, 于传昂2, 王泽诚2, 王盈盈1,*(), 解增洋1,*()   

  1. 1 济宁医学院, 基础医学院新型抗肿瘤药物分子设计与合成实验室, 山东 济宁 272067
    2 济宁医学院, 临床医学院, 山东 济宁 272067
    3 济宁医学院, 第二临床医学院, 山东 济宁 272067
  • 收稿日期:2023-09-25 录用日期:2023-11-03 发布日期:2023-11-14
  • 通讯作者: 王盈盈,解增洋 E-mail:wangyyjnmc@126.com;xiezy@mail.jnmc.edu.cn
  • 基金资助:
    教育系统省政府公派出国留学项目(鲁教外函〔2019〕27号-22);山东省大学生创新创业训练计划项目(s202210443004);济宁医学院大学生创新创业训练计划项目(cx2022050z);济宁医学院大学生创新创业训练计划项目(cx2022030z);山东省本科高校教学改革研究项目(M2023005)

Efficient Rapid Synthesis and Antibacterial Activities of Tosylhydrazones: A Recommended Innovative Chemistry Experiment for Undergraduate Medical University

Jingjie Tang2, Luying Xie2, Jiayu Liu3, Shangyu Shi2, Xinyu Sun2, Jiayang Lin2, Qikun Yang2, Chuan'ang Yu2, Zecheng Wang2, Yingying Wang1,*(), Zengyang Xie1,*()   

  1. 1 Laboratory of New Antitumor Drug Molecular Design & Synthesis, College of Basic Medicine, Jining Medical University, Jining 272067, Shandong Province, China
    2 Clinical Medicine College, Jining Medical University, Jining 272067, Shandong Province, China
    3 The Second Clinical Medicine College, Jining Medical University, Jining 272067, Shandong Province, China
  • Received:2023-09-25 Accepted:2023-11-03 Published:2023-11-14
  • Contact: Yingying Wang, Zengyang Xie E-mail:wangyyjnmc@126.com;xiezy@mail.jnmc.edu.cn

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摘要：

在有机化学实验教学过程中，实验内容通常是完成某一化合物的合成或提取，缺少对目标化合物的结构鉴定和性质检验。为了提高有机化学实验教学质量，培养学生的科研素养和创新能力。以商业易得的醛、酮和对甲苯磺酰肼为反应原料，于室温无溶剂条件下，利用研磨方法在1 min内高效快速合成磺酰腙，并对产物进行结构表征和性质研究。产物应用于抗菌实验研究时，化合物3i和3h对大肠杆菌有最好的抑制效果。实验涉及合成、TLC检测和柱色谱层析等操作，可以锻炼学生在有机化合物合成、纯化及结构鉴定等方面的操作技能。要求学生独立查阅文献，熟练掌握Origin、ChemDraw和MestRec等软件的使用，可以提升学生分析问题并解决问题的能力。改进的实验以提高学生综合素质为宗旨，适用于有机化学基础实验教学。

关键词: 无溶剂条件, 磺酰腙, 研磨方式, 抗菌性能

Abstract:

In the teaching process of the organic chemistry experiment, the content typically involves the synthesis or extraction of a certain compound, often lacking in structural identification and property testing of the target compound. To improve the quality of organic chemistry experimental teaching, and cultivate students' scientific research literacy and innovation ability, commercially available aldehydes, ketones and p-toluenesulfonyl hydrazide are used as reactants. N-tosylhydrazone derivatives were effectively synthesized within 1 min under solvent-free conditions by using a grinding method at room temperature, and the structure and properties of the products were also studied. Compounds 3i and 3h have the best inhibitory effect against Escherichia coli during antibacterial experimental research. The experiment, encompassing synthesis, TLC detection, and column chromatography operations, serves to hone students' operational skills in organic compound synthesis, purification, and structural identification. Students are required to consult literature independently and proficiently utilize software tools like Origin, ChemDraw and MestRec, which fosters their ability to analyze and resolve problems. This improved experimental framework, aimed at elevating students' comprehensive qualities, is well-suited for the foundational organic chemistry experimental teaching.

Key words: Solvent-free conditions, Tosylhydrazones, Grinding method, Antibacterial properties