Page 1 of 1

Module Code - Title:

CH4007 - ORGANIC PHARMACEUTICAL CHEMISTRY 1

Year Last Offered:

2021/2

Hours Per Week:

Lecture

2

Lab

0

Tutorial

0

Other

2

Private

5

Credits

6

Grading Type:

N

Prerequisite Modules:

CH4007

Rationale and Purpose of the Module:

To build on the functional group chemistry covered in CH4102, CH4103 and CH4104. To impart to the student a detailed understanding and working knowledge of the applied use of organic compounds as pesticides and as medicinal drugs with an emphasis on mode of action at the molecular level and on the synthesis of selected structures.

Syllabus:

Insecticides: The role of acetylcholine and acetylcholinesterase (AChE) in nerve impulse transmission; organophosphates and carbamates: Malathion, parathion and carbaryl, synthesis, mode of action as inhibitors of AchE. Herbicides: 2,4,5-T and 2,4-D, synthesis, nucleophilic aromatic substitution reactions, dioxin formation; mode of action as auxin analogs. Antibiotics: sulfonamides, synthesis, mode of action; penicillins: role of transpeptidase enzymes in bacterial cell wall synthesis, mode of action of penicillins as inhibitors of transpeptidase enzymes, synthesis of semi-synthetic penicillin stuctures. Analgesic and antiarthritic compounds: aspirin, ibuprofen and naproxen, synthesis of naproxen, resolution and racemisation aspects. Review of functional group chemistry.

Learning Outcomes:

Cognitive (Knowledge, Understanding, Application, Analysis, Evaluation, Synthesis)

Describe the role of the enzyme acetylcholinesterase (AChE) in nerve impulse transmission.Describe the role of transpeptidase enzymes in bacterial cell wall synthesis.Explain how organophosphates behave as inhibitors of AChE and thereby as insectides.Explain how nucleophilic aromatic substitution reactions occur and describe the synthesis of the herbicides 2,4-D and 2,4,5-T.Describe the mode of action, and synthesis of sulfonamides.Explain and illustrate how penicillins act as inhibitors of transpeptidase enzymes and thereby as bactericides.Explain, and illustrate using an example, the distinct stages in the preparation of a semisynthetic penicillin. Explain and illustrate synthetic routes to naproxen and identify relevant stereochemical aspects. Associate the required reagents with a series of given functional group transformations.

Affective (Attitudes and Values)

Demonstrate an appreciation of the role of organic chemistry as a fundamental molecular science.Demonstrate an appreciation of small organic molecules as enzyme inhibitors and thereby as biologically active structures.

Psychomotor (Physical Skills)

N/A

How the Module will be Taught and what will be the Learning Experiences of the Students:

This module will be taught over a 12 week period through a formal interactive lecturing mode (2 x 1 hour lectures; 1 hour tutorial per week); students will carry out an assignment involving retrieval of scientific data on a defined topic (by chemistry staff members) using online scientific literature searching. The module will be assessed by an end-of-semester written exam (85% of final marks); the assignment report (15%).

Research Findings Incorporated in to the Syllabus (If Relevant):

Prime Texts:

R. J. W. Cremlyn (1991) Agrochemicals: Preparation and Mode of Action , Wiley
L. g. copping and H. G. Hewitt (1998) Chemistry and Mode of Action of Crop Protecting Agents , Royal Soliety of Chemistry
T. J. Franklin (1998) Biochemistry and Molecular biology of Antimicrobial Action , Academic
J. B. Taylor and P. D. Kennewell (1993) Modern Medicinal Chemistry , Prentice Hall Ellis Horwood
J. Clayden, N. Greeves, S. Warren and P. Wothers (2001) Organic Chemistry , Oxford University Press
H. Arpe (1997) Ullman's Encyclopedia of Industrial Chemistry, 5th Edn. on CD-ROM , Wiley-VCH

Other Relevant Texts:

Programme(s) in which this Module is Offered:

Semester - Year to be First Offered:

Autumn - 09/10

Module Leader:

Peter.Davern@ul.ie