Organic Chemistry of Drug Molecules

Course goals

Upon successful completion of this course, students will be able to:

1. Understand the basic language of organic chemistry in terms of line-bond structures and electron-pushing notation.
2. Recognize functional groups that play an important role in molecular properties.
3. Design and conduct several basic experiments for the chemical synthesis and characterization of drug-like derivatives.
4. Name the basic chemical building blocks of biomolecules.
5. Explain the process of drug design and synthesis.
6. Search for the most appropriate literature data and reference books,
7. Effectively Work together in a group with their peers.

Content

This is an introductory course to organic chemistry of drug design and drug action.

Introduction:
What makes a molecule a drug molecule? A drug molecule is defined by its ability to regulate a biological process. Drug molecules are often expected to interact with their target (protein) thereby interfering in disease-related processes due to an alteration of the target’s (protein) function. The interaction between the drug and its target requires specific physicochemical properties to be present within the molecule. These properties are strongly related to the molecular shape and the framework of carbon and heteroatoms (e.g. O, N, F, Cl, Br, I, S) defining a unique compound. In each molecule functional groups (an assembly of atoms characteristic of chemical behaviour) determine molecular geometry, three-dimensional shape, rigidity, interaction, solubility, and reactivity.

Set up of this course:
This course provides students with basic knowledge of organic molecules. Throughout the course concepts in organic chemistry are exemplified through case studies. These case studies all revolve around a common theme: 'Drugs that Changed the World'. Over the course of seven weeks students investigate seven different drug molecules, one per week, by a plenary lecture, class meetings, lab work and practical sessions. The laboratory work in this course includes applications of NMR, UV/vis and the determination of reaction order. The chosen set up is intended to enable students to understand and to predict the molecular as well as the physicochemical properties of a molecule in relation to its structure. To understand drug chemistry and drug action it is required that students gain a basic knowledge of the role of functional groups; creating this knowledge is the red thread of this course. At the end of the course, students will be able to propose structural modifications of a particular (drug) molecule to improve biological and/or biophysical behaviour in a cellular read-out system.

Relation to other courses:
The course ‘Organic Chemistry of Drug Molecules’ runs parallel to the course ‘Physical Chemistry for the Life Sciences’, to ensure that concepts like atomic orbitals, hybridization, and bond formation are taught from a theoretical as well as a contextual perspective. In the mandatory level 2 course “Biophysical Methods and Structural Biology” the theory of NMR, MS, and fluorescence will be expanded upon and applied to the study of biological macromolecules.

Teaching format course (estimation):
Lectures 30%
Tutorials 10%
Practicals 30%
Writing 10%
Self-study 20%

This course is set up according to the ‘enquiry-based learning and teaching’ model. Rather than the teacher telling students what they need to know, active learning and student participation are key elements in this model. Students are encouraged to explore the material, ask questions, design and perform their experiments, and share ideas. Enquiry-based learning generally has four phases:  Interacting, Clarifying, Questioning, and Designing. These four phases are reflected in the course set up outlined above. 

Grading (check course manual for details):

1. Written exam (75%)
2. Lab journal (25%)
3. Mid-term exam to gain bonus points which will be added to the written exam. (Note: the grade of the written exam including bonus point will not exceed 10.0)

Minimal grade to pass each component is 5.5, and there is a requirement for attendance of each exam component.