This course systematically describes practical knowledge and theory of organic chemistry necessary for the access to biologically active compounds and pharmaceuticals. Thus, the contents of this course are individual organic reactions, synthetic methods, and utility of such products, including the handling of heterocyclic compounds and optically active compounds, both of which frequently appear as biologically active compounds and pharmaceuticals. In addition, the structural diversity of naturally occurring products, their artificial synthesis and modification based on organic chemistry, and derived medicines in this way are important subjects in this course. As a whole, this course gives lectures on not only practical organic reactions and syntheses but also the industrial production of medicines, obtained via the study of structure-activity relationship and molecular recognition taking advantage of organic chemistry.
While this course, if necessary, allows students to review the subjects on nature, reactivity, analysis, and synthesis of organic compounds mastered during Organic Chemistry I (alkanes and haloalkanes)~IV (carbonyl compounds and amines), it provides them with more practical knowledge and theory of a higher level, by discussing concrete examples of the access to biologically active compounds or pharmaceuticals. Furthermore, the students learn the utility of naturally occurring products and the importance of organic chemistry to perform the structure-activity relationship and the matching study of drugs to their receptors in the design of artificial pharmaceutical drugs starting with the former. Thus, this course has students acquire the practical ability to manage organic chemistry in the preparation of bioactive molecules and understand the broad area covered by organic chemistry including the extension to industrial production.
By the end of this course, students will be able to:
1. Understand and explain that organic chemistry plays a critical role not only in the reaction and synthesis but also in the treatment of lead compounds and the structure-activity relationship in the development of pharmaceutical drugs.
2. Understand and explain the nature, reactions, and synthesis of heterocyclic compounds frequently found in pharmaceutical drugs.
3. Understand and explain the nature, reactions, and synthesis of optically active compounds.
4. Understand and explain the diversity of structures of naturally occurring products or biomolecules and their corresponding synthetic methods.
5. Understand and explain the process of molecular modification from naturally occurring products or biomolecules to pharmaceutical drugs.
6. Understand and explain the way to industrial production of pharmaceutical drugs.
naming of medicines, lead compounds, molecular modification, structure-activity relationship, random screening, receptor, drug metabolism, heterocycles, biomolecules, natural organic compounds, pharmacokinetics, optically active compounds, asymmetric synthesis, molecular recognition, combinatorial synthesis, process chemistry
|Intercultural skills||Communication skills||Specialist skills||Critical thinking skills||Practical and/or problem-solving skills|
Lectures are given based on the documents distributed in class. In the 4th and 5th classes dealing with heterocyclic compounds, the textbook shown below will be used. Students are given concise exercise problems for the last 10 minutes of each class, and their solutions and remarks will be explained at the beginning of the next class.
|Course schedule||Required learning|
|Class 1||Organic chemistry and pharmaceutical chemistry||Understand and explain the role of organic chemistry in the development of pharmaceutical drugs.|
|Class 2||Pharmaceutical synthesis and lead compounds||Understand and explain the role of lead compounds in the synthesis of pharmaceutical drugs.|
|Class 3||Drug molecules and natural organic compound||Understand and explain the similarity and diversity of drug molecules and natural organic compounds.|
|Class 4||The structures of pharmaceutical drugs and biological activity (structure-activity relationship)||Understand and explain the importance of structures of pharmaceutical drugs and relevant structure-activity relationship and bioequivalence of functional groups.|
|Class 5||Synthesis of drug molecules ①||Understand and explain the significance and the representative methods for organic synthesis of drug molecules.|
|Class 6||Synthesis of drug molecules ②||Understand and explain the significance and the more advanced methods for organic synthesis of drug molecules.|
|Class 7||Heterocyclic compounds and pharmaceuticals||Understand and explain the nature of heterocyclic compounds in pharmaceuticals and their synthesis.|
|Class 8||Aliphatic heterocyclic compounds and pharmaceuticals||Understand and explain the nature of aromatic heterocyclic compounds in pharmaceuticals and their synthesis.|
|Class 9||Aromatic heterocyclic compound and pharmaceuticals||Understand and explain the nature of aromatic heterocyclic compounds in ¥pharmaceuticals and their synthesis.|
|Class 10||Drug molecules and pharmacokinetics||Understand and explain the synthetic design of drug molecules considering pharmacokinetics.|
|Class 11||Optically active compound||Understand and explain the nature of the optically active compounds present in many pharmaceutical structure.|
|Class 12||Asymmetric synthesis and drug||Understand and explain the asymmetric synthesis required in order to develop an optically active medicines.|
|Class 13||Molecular recognition||Understand and explain the molecular recognition necessary for functional expression of pharmaceutical products.|
|Class 14||Combinatorial synthesis||Understand and explain the combinatorial synthesis to be used in drug development early stage.|
|Class 15||Process chemistry||Understand and explain the process synthesis in drug development late stage.|
Course materials are provided during class. In the 7~9th classes dealing with heterocyclic compounds, the following is used as textbook: The Japanese translation of K. Peter C. Vollhardt, Neil E. Schore, Organic Chemistry, 6th Edition (Last volume), Chapter 25 (pp. 1383～1433), Kagakudojin; ISBN-13: 978-4759814736. (Japanese).
If necessary, references are shown in class.
Concise exercise problems 30%; Final exam. 70%.
H. Urabe: hurabe[at]bio.titech.ac.jp, 045-924-5849; T. Hata: thata[at]bio.titech.ac.jp, 045-924-5838; T. Fujie: t_fujie[at]bio.titech.ac.jp, 045-924-5712
Appointment by e-mail is recommended. H. Urabe: B2 Bldg. 11F Room# 1131; T. Hata: B2 Bldg. 11F Room# 1127; T. Fujie: B2 Bldg. 10F Room# 1022