CHEM 4000: Medicinal Chemistry

CHEM 4000 is a series course.  This particular offering of CHEM 4000 is a senior organic chemistry course with a strong pharmaceutical slant.  The pre-requisite for Medicinal Chemistry is CHEM 2600 (Organic Chemistry II), and concepts from both CHEM 2500 and CHEM 2600 will be used regularly.  While additional chemistry background is always welcomed, it is not required.

Medicinal chemists use organic chemistry to make drug targets.  In this course, students will develop some of the skills necessary to this endeavor, particularly retrosynthetic analysis (breaking larger molecules into smaller parts).  The text (Elements of Synthesis Planning) introduces the method of breaking down molecules into "synthons", an approach that will be used extensively.  

Additionally, previous syntheses of drugs and drug targets will be used to help students improve their understanding of reaction mechanisms, add to their vocabulary of reactions, and evaluate the strengths and weaknesses of existing syntheses.  The principles of green chemistry will be discussed, and will be the focus of the last assignment. 

Course Structure:  Students will be assigned readings from the text which will provide a starting point for discussion on Monday and Wednesday classes.  New reactions relevant to the day’s discussion may also be introduced.  Friday classes will be structured in “problem set” format in which students take turns working through steps of a synthesis with the help of peers and instructor, when necessary. 

In order to encourage active involvement in both class discussions and problem set classes, participation marks will form a significant portion of each student’s overall grade.  Each student can earn a maximum of 40 points which will then be divided by two to obtain a score out of 20.  Taking a turn at the board during problem set earns a student 5 points. Active participation in class discussions (or helping the person at the board during problem set) earns a student 1 point (maximum 1 point per class; however, this point can be earned in addition to the 5 points for taking a turn at problem set).  To earn participation points, a genuine effort must be made to contribute; credit will not be given for random guesses or other halfhearted attempts.  Participation marks do not, however, depend on answers being correct.

Information provided on this website includes:

CHEM 4000 Reading Guide (Spring 2022)113 KB
CHEM 4000 Course Outline (Spring 2024)182 KB

CHEM 4000 Assignments

Assignments will be posted here for the Winter 2024 semester.

CHEM 4000 SciFinder Assignment (Winter 2024)201 KB
CHEM 4000 Mechanistic Assignment (Winter 2024)259 KB

CHEM 4000 Lecture Notes (Findlay)

These are the most recent versions of my lecture notes for CHEM 4000 (from Spring 2022).

These are skeleton notes; it is intended that you complete them when you attend class.  Admittedly, the first set isn't very skeletal...  :-) 

Topics are numbered to match the chapters in the textbook (Elements of Synthesis Planning by R.W. Hoffmann).

CHEM 4000 Topic 0: Drug Discovery and Design160 KB
CHEM 4000 Topic 1: Introduction232 KB
CHEM 4000 Topic 2: Functional Group Oriented Bond-Sets221 KB
CHEM 4000 Topic 3: Skeleton Oriented Bond-Sets180 KB
CHEM 4000 Topic 4: Building Block Oriented Synthesis487 KB
CHEM 4000 Topic 5: Basis for Planning123 KB
CHEM 4000 Topic 6: Formation of Cyclic Structures277 KB
CHEM 4000 Topic 7: Protecting Groups85 KB
CHEM 4000 Topic 8: Ranking of Synthesis Plans71 KB
CHEM 4000 Topic 9: Practicing Retrosynthesis49 KB
Appendix to Topic 1: Steroids from Isoprene Building Blocks (Lanosterol from Squalene)42 KB

CHEM 4000 Practice Questions

Below are a couple of sets of practice questions I put together for practice before each test.

I have also created pages with assignments and tests from previous semesters that might prove useful practice:

Pre-Midterm Practice Questions on Chapters 1-3101 KB
Pre-Midterm Practice Questions on Chapters 1-3 (Answers)352 KB
Pre-Final Practice Questions on Chapters 1-8173 KB
Pre-Final Practice Questions on Chapters 1-8 (Answers)426 KB

CHEM 4000 Problem Set Molecules

The presentations below give a bit of background information on the molecules that we "make" in class every Friday.  I do not consider this material testable; it's purely for interest.

Rofecoxib (Vioxx)107 KB
Fexofenadine (Allegra)97 KB
Gefitinib (Iressa)103 KB
Ticlopidine (Ticlid) and Clopidogrel (Plavix)100 KB
Minoxidil (Rogaine)98 KB
Tazarotene (Tazorac)97 KB
Loratadine (Claritin) and Desloratadine (Clarinex)107 KB
Ciprofloxacin (Cipro)48 KB
Sildenafil (Viagra)64 KB