ORGANIC CHEMISTRY OF DRUG SYNTHESIS AND ACTION FALL 2020

INSTRUCTOR: Dr. Craig E. Masse (cmasse@comcast.net)

Online (live) web conference

Textbooks:
Recommended –

Contemporary Drug Synthesis, Jie-Jack Li, Douglas S. Johnson, Drago R. Sliskovic, Bruce R.
Roth (Wiley-Interscience)

The Organic Chemistry of Drug Design and Drug Action, 2nd Edition, R. B. Silverman
(Elsevier)
The Art of Writing Reasonable Organic Reaction Mechanisms, 2nd Edition
Robert B. Grossman (Springer-Verlag)
An Introduction to Medicinal Chemistry, 4th Edition, G. L. Patrick (Oxford)

Course Description:
This course will place an emphasis on the application of organic synthesis towards the
development of pharmaceutical targets at both the medicinal and process chemistry level. The
class will examine the macromolecular targets of some of the more popular types of
pharmaceutical therapies that exist today using case histories of modern drug molecules for each
topic. The lectures will be arranged and discussed on the basis of the chemical structure of the
pharmaceutical agent with the relevant mechanistic organic and biochemical concepts discussed
in terms of the mode of drug action.

• Office Hours: Dr. Masse will hold a weekly office hour (Tuesday’s 8-9pm) and will also be
available by appointment.
Grading:
• Exams. There will be two midterm exams given on the dates noted in the schedule at the end of the
syllabus. Each exam will cover material from 3-4 lectures, but the exams will be cumulative and
material from ANY previous lecture can be included. There will be NO MAKEUP MIDTERM
EXAMS! This is course policy and there are NO exceptions.

• Presentation (Graduate Students). Students taking the course for graduate credit will select a
current (after 1996) journal article involving the medicinal or process route to a pharmaceutical agent
and deliver a 15-minute presentation on the article to the class.
• Papers. All Students will select a recently (after 1996) FDA approved small molecule drug and
prepare a summary (4-5 pages) of its synthesis and mechanism of action. The paper will serve as the
final exam for the course.

• Course Grades. The final course grades will be based on a total of 500 points with 200 points (2 x
100 points) for the midterm exams, 150 points for the in-class presentation (graduate credit only) and
150 points for the final paper. There are NO MAKEUP MIDTERM EXAMS.

Course Grading Total

Points
Midterm Exams (100 pts x 2) 200
In-Class Presentation (graduate 150
credit)
Final Paper 150
Total Points 500

• Academic Honesty. The vast majority of you will conduct yourself in an honest manner without
having read the following disclaimer, so it is unfortunate that the following topic bears mentioning.
In registering for this course, students agree to abide by the policies printed in the Extension School
catalogue, which contains brief descriptions of plagiarism, cheating, and computer network abuse.
Students found guilty of academic dishonesty by the Administrative Board face a range of sanctions,
including probation, required withdrawal from a course, suspension from the Extension School for
one or more terms, and required withdrawal from an Extension School degree or certificate program.
Academic dishonesty in any course taught by Dr. Masse will be met with the harshest possible
consequences, which can result in a lasting effect on your future plans. Out of respect for yourself
and your fellow students, you are urged not cheat on exams.
You are responsible for understanding Harvard Extension School policies on academic integrity
(www.extension.harvard.edu/resources-policies/student-conduct/academic-integrity) and how to use
sources responsibly. Not knowing the rules, misunderstanding the rules, running out of time,
submitting "the wrong draft", or being overwhelmed with multiple demands are not acceptable
excuses. There are no excuses for failure to uphold academic integrity. To support your learning
about academic citation rules, please visit the Harvard Extension School Tips to Avoid Plagiarism
(www.extension.harvard.edu/resources-policies/resources/tips-avoid-plagiarism), where you'll find
links to the Harvard Guide to Using Sources and two, free, online 15-minute tutorials to test your
knowledge of academic citation policy. The tutorials are anonymous open-learning tools.

• Attendance: please see Harvard Extension School policy

(https://www.extension.harvard.edu/resources-policies/student-conduct/expectations)
Preliminary Lecture and Exam schedule
Date Topics
Sept. 2 Lecture #1: Intro to Organic Chemistry of Drugs (incl. skills check assignment)
Sept. 9 Lecture #2: Aspartyl & Serine Protease Inhibitors
Sept. 16 Lecture #3: Development of Anticoagulant Agents
Sept. 23 Tutorial on Harvard’s Electronic Resources
Sept. 30 Lecture #4: Development of Anticoagulant Agents (cont)
Oct. 7 Midterm Exam #1
Oct. 14 Lecture #5: Development of Treatments for Alzheimer’s Disease
Oct. 21 Lecture #6: Treatments for Alzheimer’s Disease (cont.)
Oct. 28 Lecture #7: Development of Anti-Emetic agents
Nov. 4 Lecture #8: Development of Non-Steroidal Anti-Inflammatory agents (NSAID)
Nov. 11 Midterm Exam #2 (comprehensive)
Nov. 18 Lecture #9: Development of COX-2 Inhibitors
Nov. 25 No Lecture- Thanksgiving break
Dec. 2 Lecture #10: In-Class Presentations
Dec. 9 Lecture #11: In-Class Presentations
Dec. 16 Lecture #12: Guest Lecture & Final Paper Due

Disability Services:

The Extension School is committed to providing an accessible academic community. The Disability
Services Office offers a variety of accommodations and services to students with documented
disabilities. Please visit www.extension.harvard.edu/resources-policies/resources/disability-services-
accessibility for more information.

Requesting a Letter of recommendation

When requesting a letter of recommendation, you must provide the following:

- A copy of your CV
- A copy of the “Personal Inventory for Medical School Applicants”, if you are part of the Harvard
Careers Program, OR a similar inventory of essays/questions/answers that indicates what your
career plans are, why you are pursuing this career, how previous experiences and/or mentors have
influence you. Remember, the more information I have, the better my recommendation can be.
- The deadline for the recommendation
- An addressed and stamped envelope or secure link to send the recommendation into the appropriate
school/agency