Experiments of Medicinal Chemistry(Second Edition)mainly includes five parts:chemical drug synthesis experiments,experimental report templates,commonly used instruments,reference answers to thinking questions and boiling points and dielectric constants of commonly used solvents.In the part of chemical drug synthesis experiments,19 drugs were arranged in the order from basic to comprehensive.This textbook emphasizes the relationship between theoretical teaching and experiment of pharmaceutical chemistry,and pays attention to training students experimental ability and scientific research quality.In an effort to adapt to the contemporary trend of internationalization of higher education,this textbook is compiled in a ChineseEnglish bilingual system.This textbook is suitable for the experimental teaching of pharmacy students(including foreign students)in medical colleges and universities.《药物化学实验(双语)(Experiments of Medicinal Chemistry)》(第二版)主要包括化学药物合成实验、实验报告模板、常规仪器、思考题参考答案以及常用溶剂的沸点和介电常数五个部分。化学药物合成实验部分按照基础操作到综合实验的顺序安排了19个药物的合成实验,强调了药物化学理论教学与实验的关联,关注学生实验能力和科研素质的培养。为适应高等教育国际化的趋势,本教材采用中英双语体系编写。《药物化学实验(双语)(Experiments of Medicinal Chemistry)》(第二版)适用于高等医药院校药学类专业学生(包括留学生)的实验教学。
目錄:
Experiment 1 Recrystallization of Acetanilide 1
实验一 乙酰苯胺重结晶 5
Experiment 2 Synthesis of Aspirin 9
实验二 阿司匹林的合成 14
Experiment 3 Synthesis of Paracetamol 18
实验三 对乙酰氨基酚的合成 22
Experiment 4 Synthesis of Benorilate 26
实验四 贝诺酯的合成 31
Experiment 5 Synthesis of Sulfacetamide Sodium 36
实验五 磺胺醋酰钠的合成 42
Experiment 6 Synthesis of Benzocaine Intermediate Ethyl pNitrobenzoate 47
实验六 苯佐卡因中间体对硝基苯甲酸乙酯的合成 53
Experiment 7 Synthesis of Pd/TBCOF supported Nanocatalysts (Virtual Simulation Experiment) 58
实验七 Pd/TBCOF负载型纳米催化剂的合成(虚拟仿真实验) 64
Experiment 8 Synthesis of Benzocaine(Virtual Simulation Experiment) 69
实验八 苯佐卡因的合成(虚拟仿真实验) 77
Experiment 9 Synthesis of Lidocaine Hydrochloride 83
实验九 盐酸利多卡因的合成 88
Experiment 10 Synthesis of Dyclonine Hydrochloride 93
实验十 盐酸达克罗宁的合成 99
Experiment 11 Synthesis of Nitrendipine 104
实验十一 尼群地平的合成 109
Experiment 12 Synthesis of Ciprofloxacin Monohydrochloride Monohydrate 114
实验十二 盐酸环丙沙星的合成 120
Experiment 13 Synthesis of Phenytoin Sodium 125
实验十三 苯妥英钠的合成 131
Experiment 14 Synthesis of Neostigmine Bromide 136
实验十四 溴新斯的明的合成 142
Experiment 15 Synthesis of Boceprevir 147
实验十五 波普瑞韦的合成 154
Experiment 16 Synthesis of Nirmatrelvir 161
实验十六 奈玛特韦的合成 168
Experiment 17 Synthesis of Sofosbuvir 174
实验十七 索磷布韦的合成 181
Experiment 18 Synthesis of Azvudine 187
实验十八 阿兹夫定的合成 193
Experiment 19 Synthesis of Olverembatinib 199
实验十九 奥雷巴替尼的合成 205
Appendix 1 Experimental Report Template 210
附录一 实验报告模板 213
Appendix 2 Reference Answer for the Discussion Questions 216
附录二 思考题参考答案 225
Appendix 3 Common Instruments(常用仪器) 233
Appendix 4 The boiling point and dielectric constant of the commonly used solvents 235
附录四 常用溶剂的沸点和介电常数 236
References(参考文献) 237
內容試閱:
前言
2019年,全国高等教育药学类规划教材《药物化学实验双语教程(Experiments of Medicinal Chemistry)》第一版出版。该教材对药学类专业学生,尤其是对留学生的教学发挥了重要作用。为进一步适应国家和社会对创新型药学人才培养的需求和本科教学国际化的发展趋势,我们在第一版教材的基础上进行修订,编写了《药物化学实验(双语)(Experiments of Medicinal Chemistry)》第二版。
与第一版相比,本教材保留原有的10个实验,新增有关地平类药物、肽类药物、核苷类药物、替尼类药物合成的9个实验,总计为19个实验。此外,本教材还增加了苯佐卡因合成的虚拟仿真实验(若需要开展该虚拟仿真实验,请通过邮件形式联系编者,liwen@zzu.edu.cn),丰富了药物的结构类别、合成方法和学习方式。本教材中实验三至实验八、实验十二,均以二维码形式提供了数字化内容,主要为实验操作演示视频资料。更为重要的是,新增的实验除了包含近年来新上市的药物,也涉及具有我国自主知识产权的创新药物和编者的科研成果。
此次修订在每个药物的背景知识部分,增加了化合物活性评价方法,以加深学生对结构活性关系的理解;在每个药物的实验原理部分,增加了知识点的内容,以帮助学生理解和掌握学习重点;在每个药物的合成实验中,新增了药物含量的测定方法,以培养学生药品质量意识。在苯佐卡因合成的虚拟仿真实验中,增加了化合物的核磁共振氢谱解析,以培养学生的结构确证能力。本教材的内容既重视对学生药物合成能力的培养,也充分体现了药物设计化学合成结构确证活性评价含量分析等知识的综合性,有利于培养学生灵活运用药学综合知识的能力,是创新型人才培养的一种积极尝试。
本教材中,实验一、实验二由李雯和郑一超编写,实验七、实验八、实验九和实验十四由李雯编写,实验三、实验四由陈亚静编写,实验五由丁丽娜编写,实验六由张恩编写,实验十由孙凯编写,实验十一由段迎超编写,实验十二由郑一超编写,实验十三由张赛扬编写,实验十五由桑鹏编写,实验十六由石岩编写,实验十七由孟勇刚编写,实验十八由常晓宇编写,实验十九由陆小云编写。本教材由尤启冬审定。教材中药物分子和靶标的作用机制部分由丁丽娜及研究生阎影、马超亚、王志正、高琦冰、孙旭东、杨晶、刘欢和王兵丽等借助MOE软件作图及编写,教材中有关药物活性评价方式的部分由郑一超进行编写。留学中国的博士研究生Muhammad Zeeshan、研究生朱林元参与了本教材的语言修订工作。
本教材采用中英双语体系编写,可用于高等医药院校药学类专业学生(包括留学生)的实验教学。
编者
2024年10月
Preface
In 2019,the editor compiled and published the first edition of the national higher education pharmacy planning textbook Experiments of Medicinal Chemistry.This textbook has played an important role in teaching pharmacy major students,especially international students.In order to further meet the needs of the country and society for the cultivation of innovative pharmaceutical talents and the trend of internationalization of undergraduate teaching,we have revised the first edition of the textbook and compiled the bilingual textbook Experiments of Medicinal Chemistry(Second Edition).
Compared with the first edition of the textbook,this textbook retains the original 10 experiments and adds 9 new experiments,for a total of 19 experimental contents.The 9 newly added experiments are synthesis experiments of dipine drugs,peptide drugs,nucleoside drugs,and tinib drugs.In addition,this textbook also includes virtual simulation experiments on the synthesis of benzocaine(If you need to conduct virtual simulation experiments, please contact liwen@zzu.edu.cn),enriching the structural categories,synthesis methods,and learning methods of drugs.The digital contents of experiments three to eight and twelve in this textbook is provided in the form of QR codes,mainly including demonstration videos of experimental operations.The newly added experiments not only include newly launched drugs in recent years,but also involve innovative drugs with independent intellectual property rights in China and the results of the editor‘s scientific research work.
This revision has added compound activity evaluation methods in the background knowledge section of each drug to deepen students’ understanding of structureactivity relationships.In the experimental principle section of each drug,knowledge points have been added to help students understand and master the key learning points.In each drug synthesis experiment,a new method for determining drug content has been added to cultivate students‘ concept of drug quality.In the virtual simulation experiment of benzocaine synthesis,nuclear magnetic resonance hydrogen spectrum analysis of the compound was added to cultivate students’ structural confirmation ability.The content of this textbook not only emphasizes the cultivation of students‘ ability in drug synthesis,but also fully reflects the comprehensiveness of knowledge such as drug designchemical synthesisstructural confirmationactivity evaluationcontent analysis.It is conducive to cultivating students’ ability to flexibly apply pharmaceutical comprehensive knowledge and is a positive attempt to cultivate innovative talents.
Experiments 1 and 2 of this textbook were written by Wen Li and Yichao Zheng,experiments 7,8,9,and 14 were written by Wen Li,experiments 3 and 4 were written by Yajing Chen,experiment 5 was written by Lina Ding,experiment 6 was written by En Zhang,experiment 10 was written by Kai Sun,experiment 11 was written by Yingchao Duan,experiment 12 was written by Yichao Zheng,experiment 13 was written by Saiyang Zhang,experiment 15 was written by Peng Sang,experiment 16 was written by Yan Shi,experiment 17 was written by Yonggang Meng,experiment 18 was written by Xiaoyu Chang,experiment 19 was written by Xiaoyun Lu,and the entire book was reviewed by Qidong You.The part of the textbook on the mechanism of action of drug molecules and targets was prepared by Lina Ding and postgraduate students Ying Yan,Chaoya Ma,Zhizheng Wang,Qibing Gao,Xudong Sun,Jing Yang,Huan Liu,and Bingli Wang using MOE software for diagrams and writing.The section on drug activity evaluation methods in the textbook was written by Yichao Zheng.Muhammad Zeeshan,a doctoral student studying in China,and Linyuan Zhu,a graduate student,participated in the language editing work of this textbook.
This textbook is written in a bilingual system of Chinese and English,and can be used for experimental teaching of pharmacy majors(including international students)in higher medical colleges.
Editors
October 2024
前言(第一版)
为适应我国本科教学国际化的发展趋势,根据药物化学实验课程的基本要求,结合我们多年的教学经验和科研工作,编写了这本《药物化学实验双语教程(Experiments of Medicinal Chemistry)》。
本书包括10个化学药物合成实验,实验一至实验八为我们多年药物化学实验教学实践的总结,实验九和实验十为编者科研工作的结果。在化学药物合成实验的安排上,本书按照从基础操作到综合实验的顺序进行编写;在内容上,本书不仅给出了实验原理、操作过程、注意事项和思考题,而且给出了药物分子和靶标的作用机制图示、主要原料和中间体的物理常数、实验装置、安全提示和思考题参考答案。旨在强调药物化学理论教学与实验的关联,关注学生实验能力和科研素质培养。10个化学药物合成实验的难易程度和实验学时有明显的区分度,可满足不同专业和不同层次学生的教学需求。
本教材的实验一、实验二、实验七、实验九由李雯、刘宏民编写,实验三、实验四由陈亚静编写,实验五由丁丽娜编写,实验六由张恩编写,实验八由郑一超编写,实验十由张秋荣编写,全书由尤启冬教授审订。书中药物分子和靶标的作用机制部分由丁丽娜及其研究生阎影、马超亚、王志正、高琦冰、孙旭东和杨晶等借助MOE软件进行模拟研究编写而成。留学中国的博士研究生Moges Dessale Asmamaw、研究生常英杰、李瑞鹏及本科生朱林元参与了本书的语言润色工作。药物化学实验双语教材的建设,任重而道远。
《药物化学实验双语教程(Experiments of Medicinal Chemistry)》采用中英双语体系编写,可作为普通高等医药院校药学类各专业学生(包括留学生)的实验教材,也可供其他药学相关专业师生参考使用。
编者
2019年3月
Preface(First Edition)
In order to adapt to the development trend of internationalization of undergraduate teaching in our country, according to the basic requirements of pharmaceutical chemistry experiment course combined with our years of teaching experience and scientific research work, this ”bilingual course of pharmaceutical chemistry experiment” has been compiled.
In this textbook, 10 synthetic experiments of chemical drugs are included.Experiments 1 through 8 are the summaries of many years teaching practices, Experiments 9 and 10 are the results of the editors‘ scientific research work.They are arranged by the order from basic to comprehensive gradually.In each experiment, more than the experiment principle, operation process, notes and discussion questions are given, the action mechanism diagrams of drug molecule and target, physical constants of key raw materials and intermediates, experimental equipments, safety tips and reference answers of discussion questions are described.This textbook emphasizes the relationship between theoretical teaching and experiment of pharmaceutical chemistry, and pays attention to the cultivation of students’ experimental ability and scientific research quality.There is a clear distinction between the difficulty and time of 10 experiments to meet the teaching needs of students from different majors and levels.
Experiments 1, 2, 7 and 9 of this textbook were written by Wen Li and Hongmin Liu, Experiments 3 and 4 by Yajing Chen, Experiment 5 by Lina Ding, Experiment 6 by En Zhang, Experiment 8 by Yichao Zheng and Experiment 10 by Qiurong Zhang.This textbook was revised by Professor Qidong You.The mechanistic studies between the drug molecule and the corresponding target were investigated and written by Lina Ding and her graduate students Ying Yan, Chaoya Ma, Zhizheng Wang, Qibing Gao, Xudong Sun and Jing Yang with the help of MOE software.We appreciate the foreign PhD student Moges Dessale Asmamaw, graduate students Yingjie Chang, Ruipeng Li and undergraduate student Linyuan Zhu who involved in the language correction of this textbook.The construction of bilingual textbooks is on the developing way.
This textbook is compiled in a ChineseEnglish bilingual system and can be used in the experimental teaching of pharmaceutical students (including foreign students) in medical colleges and universities.
Editors
March 2019