PH3S105 - Topics in Medicinal Chemistry 01 Sep 2023 - 31 Jul 2029 | Version 2

Associated Module Information

Module Code: PH3S105
Module Title: Topics in Medicinal Chemistry
Faculty: Faculty of Computing, Engineering and Science
Faculty Group: Chemical and Environmental Sciences
Faculty Sub Group: Chemical and Environmental Sciences
Module Leader: Rehana Karim
Module Team: Paul Jones, Suzanna Kean
First Intended Intake: SEP 2018 Final Year of Intake:
Date Closed:
Credit Value: 20 Credit Level: 6
Language: English
Percentage of Module Taught in Welsh: 0
Equivalent Module:
HECOS codes: 100420 - medicinal chemistry
HECOS Code Weighting: 100

Document Version Information

Version 2
Valid From 01 Sep 2023
Valid To 31 Jul 2029

Module Aims

This module aims to impart knowledge to students of more advanced and applied chemistry topics that underpin some of the current aspects of modern drug design and pharmaceutical chemistry.

Students prior knowledge of intermolecular forces is expanded upon and applied to the design of complex molecular systems with specific structures and function (e.g., drug delivery devices).

Students are introduced to some fundamental topics in bioinorganic chemistry and their direct application to human health.

Students' knowledge of organic synthesis is extended with focus on reactions applicable to the (bio)synthesis of pharmaceutics and natural products of therapeutic value, in addition to exploring their toxicology and the role of natural products in drug discovery.

Content Summary

1.Molecular recognition

Intermolecular forces of interaction, their interplay, how they can be tailored, how they govern molecular shape/complex formation/molecular recognition.

Host/guest complexes: their dynamics, the formation of binary/ternary/quarternary systems, intercalation/encapsulation.

Chiral recognition (the 'three point rule' versus the 'lock and key' mechanism of Emil Fischer)

The importance of the role that molecular recognition plays in governing all biological systems.

Introduction to supramolecular chemistry: the design of chemical sensors, molecular devices, drug delivery systems etc.

2. Pharmaceutical Bioinorganic Chemistry and Healthcare

The Elemental Composition of the Human Body: Metals and human health. Supplying elements to the body.

Chemical speciation: Coordination metal-ligand selectivity, chemical speciation modelling. Chelation, ligands and drugs, chelating drugs designed for mobilising and excreting metal ions.

Delivery of trace elements to humans: Means of mineral supplementation, absorption of ligands from the GI tract, iron, zinc and copper supplementation, biochemistry of trace element delivery.

Agents containing metals: Health foods, healthcare agents, therapeutics, anticancer compounds, ulcer therapy using bismuth compounds, parental nutrition, wound healing products, radioprotective agents.

Chelating Agents: Selectivity of ligand drugs for metal ions using formation constant data, EDTA, DTPA etc. Invivo chelation of radionuclides.Drug synthesis/Toxicology/Natural product chemistry

3.1.             Drug synthesis/Toxicology/Natural product chemistry

Polar Rearrangements: Introduction to rearrangement reactions of carbocations i.e. 1,2-hydride shift and1,2-methyl shift.  Rearrangements to electron deficient oxygen and nitrogen: Beckman and Hofmann rearrangements and related reactions, Bayer-Villiger and Hydroperoxide reactions. Application of such reactions in the design of pharmaceutics.

Reactive Intermediates: Introduction to molecular and electronic structure of neutral intermediates i.e. radicals, carbenes and arynes. Applications of reactive intermediates in organic synthesis/pharmaceutics/natural products.

General Toxicology: General toxicology includes xenobiotics biotransformation, molecular mechanisms of toxicity and a review of the different classes of toxic substances such as natural products, pharmaceutics/polyaromatic hydrocarbons and illicit drugs.

Natural Product Chemistry: Introduction to terpenes, biosynthesis of terpenes and steroids.

Learning and Teaching Methods

Activity Type Hours
Lecture 24
Practical classes and workshops 4
Independent Study 58
Directed Study 100
Formative Assessment - Independent 2
Tutorial 14
Total Hours Selected 202

Learning Outcomes

# Learning Outcome
LO1 Demonstrate a knowledge of molecular recognition, bioinorganic principles and synthetic transformations/natural products (and other compounds of interest) and their role in defining the structure and function of advanced pharmaceuticals.
LO2 Apply taught theory to the rational design or explanation of action of advanced drugs, drug delivery devices, or other advanced pharmaceutical chemical entities

Module Requisites

N/A

Assessment Criteria

Assessment Category Assessment Type Description Duration Word Count Weight (%) Best of? Pass Mark
Written Assignment (CW) Report (CW) 1 Written assignment on the topics of polar rearrangements/reactive intermediates/general toxicology and natural products 0 3000 60 No 40
Asynchronous Assessment Literature/book/paper review 1 Students to source and critically review a recent publication on topics presented in the module. 0 2000 40 No 40

Assessment Matrix

Assessment Type Learning Outcomes
LO1 LO2
Report (CW) 1 ✔ ✔
Literature/book/paper review 1 ✔ ✔

Reading List

D. M. Taylor, D. R. Williams, Trace Elements Medicine and Chelation Therapy, 1995, RSC Press

P. Beer, P. Gale, D. Smith, Supramolecular Chemistry , 1999, Oxford University Press.

J.-M. Lehn, Supramolecular Chemistry-Concepts and Perspectives, 1995, Wiley-VCH.

A. Burrows, J. Holman, A. Parsons, G. Pilling, G. Price, Chemistry3, 2013, 2nd Ed., Oxford University Press.

D. E. Fenton, Biocoordination Chemistry, 1995, Oxford University Press.

D. Rehder, Bioinorganic Chemistry, 2014, Oxford University Press.

Andew R. Leach, “ Molecular Modelling: Principles and Applications”, 2nd edition (2001), Prentice Hall (ISBN: 0-582—38210-6).

J. Clayden, N. Greeves and S. Warren. Organic Chemistry, 2nd edn.,  Oxford University Press, Oxford, 2012.

P. C. Burcham, An Introduction to Toxicology, Springer, 2013.

A.W. Hayles, T. Wang, D. Dixon, T. A. Loomis, Loomis's Essentials of Toxicology, Academic Press, 5th edn., 2019.

J A Timbrell Introduction to Toxicology, Taylor and Francis.

G. L. Patrick,  An Introduction to Medicinal Chemistry,  Oxford University Press, Oxford, 5th edn., 2013.

G. L. Patrick,  An Introduction to Drug Synthesis, Oxford University Press, Oxford, 2014.

J. Barber, C. Rostron, Pharmaceutical Chemistry, Oxford University Press, Oxford, 2013.