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Organic and Medicinal Chemistry

  • Module code: CH5002
  • Year: 2018/9
  • Level: 5
  • Credits: 30
  • Pre-requisites: CH4001 or CH4005
  • Co-requisites: None

Summary

This is a core module Level 5 module for the Chemistry and Pharmaceutical Science fields.

The module seeks to develop and expand your knowledge of both Organic Chemistry and Medicinal Chemistry subject areas and introduces important principles, reactions and mechanisms in organic chemical reactivity as well as basic mechanisms of drug action. It develops your understanding of the methodology of organic synthesis following concepts introduced at level 4 and includes important organic chemistry topics such as carbanion reactivity of carbonyl compounds, the reactions of aromatic and heteroaromatic compounds, stereochemistry, asymmetric synthesis and retrosynthesis

It also introduces the specific reasons why a small amount of a drug molecule can exert a complex biological response. It uses examples from a range of medicinal areas in order to illustrate these key processes as well as giving an introduction on the ideas of drug design and the role this plays in the modern pharmaceutical industry.

This module also gives you experience of using spectroscopic techniques for chemical structure elucidation. Lectures and workshops are designed to develop your problem solving and team working skills. Practical skills will also be developed during two 3-hour laboratory experiments from week 9-12 of teaching block 1. These experiments will reinforce the concepts of enolate and aromatic chemistry taught during teaching block 1. In teaching block 2, you will also present a poster concerning a medicinal natural product, to integrate organic synthesis and medicinal chemistry in a real-world context. This module is essential those wishing to take the more advanced Level 6 Organic Chemistry modules.

Aims

  • To extend knowledge and understanding of key topics in organic chemistry and introduce basic concepts of medicinal chemistry.
  • To improve students' skills and confidence in drawing reaction mechanisms, predicting reaction outcomes and identifying possible synthetic routes to target compounds.
  • To develop additional skills such as: problem solving, laboratory skills, communications and team working skills.

Learning outcomes

On successful completion of the module, students will be able to:

  • Demonstrate a comprehensive knowledge of the synthesis, properties, reactivity and applications of aromatic and carbonyl compounds, particularly enolates, in synthetic and pharmaceutical chemistry.
  • Discuss advanced stereochemistry concepts including the importance of stereochemistry in the design of drugs and the resolution and synthesis of chiral compounds.
  • Describe the structures and properties of simple molecules of biological importance such as proteins, carbohydrates and fatty acids.
  • Apply the principles of retrosynthetic analysis, chemoselectivity and protecting group strategy to devise potential routes for the synthesis of organic compounds
  • Discuss the role of SAR, organic synthesis and other approaches to drug design and drug delivery and the structure, function and mode of action of therapeutic drugs.
  • Contribute to team work and present the team results using key communication skills.

Curriculum content

  • Overview of carbonyl chemistry: tautomerism; formation and stability of enolates; aldol, Claisen and related reactions; alpha alkylations.
  • Difunctional aliphatic compounds: ethyl acetoacetate and diethyl malonate and their uses in the synthesis of ketones and acids.
  • Enamines and other enolate equivalents in synthesis.
  • a,b-Unsaturated carbonyl compounds: conjugate and Michael additions
  • Electrophilic substitution of benzene; second and third substitutions of benzene derivatives; activating and directing effects of substituents.
  • Diazonium salts and their synthetic applications.
  • Nucleophilic aromatic substitution; formation and reactivity of benzynes.
  • Polycyclic aromatic compounds: naphthalene, anthracene and phenanthrene.
  • Heteroaromatic compounds: structure, aromaticity, synthesis and reactivity of pyridine, pyrrole, furan and thiophene, pyridine derivatives, indole, quinoline; the synthesis and properties of selected azoles, diazines and purines.
  • Stereochemistry: enantiomers, diastereomers and atropisomers; Fischer projections; resolution of asymmetric compounds; basic introduction to asymmetric synthesis.
  • Selectivity in synthesis: chemoselective reagents, protecting groups and their application in the synthesis of pharmaceutical agents.
  • Introduction to retrosynthetic analysis.
  • Conformational analysis, stability and reactivity of simple cycloalkanes.
  • Introduction to biochemical compounds: carbohydrates, fatty acids, nucleic acids and proteins.
  • An introduction to drug action in terms of receptor theory; drug receptor binding interactions: Chirality, 3D binding models and the drug effect; agonist and antagonist.
  • Bonding in medicinal systems; SAR and drug design
  • Mode of action of a range of antibiotics: beta lactams, sulfonamides, clavulanic acid and strategies to treat penicillin-resistant bacteria.
  • The nervous system. Neurotransmitter mimics and their pharmaceutical use.
  • Alkaloids-examples of drugs.

Teaching and learning strategy

The topics described in the sections above will be delivered via two one-hour lectures each week used to present the core material. These are supported by two one-hour workshops each week that are used to reinforce the learning of the lecture material and to provide practice at problem solving including writing reaction mechanisms and interpretation of spectra. The workshops will also provide opportunities for students to get feedback from staff on their progress. One further hour each week (weeks 12-27) will be used to develop group working skills. The group work will focus on synthetic and biochemical aspects of medicinal natural products, as well as medicinal chemistry and medical applications.

Students will also carry out 2 three-hour practical assignments (weeks 9-12), which will be assessed on the basis of product samples and a full written report.

Breakdown of Teaching and Learning Hours

Definitive UNISTATS Category Indicative Description Hours
Scheduled learning and teaching 48 one hour lectures 48 one hour workshops 9 one hour group work classes 6 two hour poster presentations 2 three hour laboratory classes 123
Guided independent study Recommended reading Formative assessment Summative assessment tasks Exam revision 177
Total (number of credits x 10) 300

Assessment strategy

During the year there will be opportunities for both formative and summative assessment. The assessment strategy in this module is designed so that feedback from formative assessments will feed forward into summative assessments. Students will mainly be prepared for the assignments in the workshops and by regular formative tests. During the workshops questions similar to exam questions will be analysed and answered.

The two practical classes will each be summatively assessed on the basis of a proforma and samples submitted. The two classes together will be worth 10% of the final module mark.

An initial formative assignment (in the form of an in-class test) will be given in the second half of the first term. The feedback from the assignment will be useful in preparation for a second in-class test in January where questions similar to exam questions will be proposed. These formatively assessed mock exams will be 2 hours long and will be compulsory.

The group work (in the form of a poster project) will continue throughout the year and each group will be assigned a natural product to research at the beginning of the year. Groups will be composed of 5-6 members and each member in the group will work on a different aspect of this topic to research. The work will finish with a summatively assessed group presentation, which together with attendance and a peer mark will be worth 30% of the final module mark.

The final exam is 3 hours long and students will be required to answer both short and long answer questions. The final exam will be worth 60% of the overall module mark.

Mapping of Learning Outcomes to Assessment Strategy (Indicative)

Learning Outcome Assessment Strategy
1) Demonstrate a comprehensive knowledge of the synthesis, properties, reactivity and applications of aromatic and carbonyl compounds, particularly enolates, in synthetic and pharmaceutical chemistry. Formative assessment and feedback will be provided during workshops and the team work sessions as well as via on-line material for selected topics and the mock exam. This learning outcome will be summatively assessed in the exam as well as in the Poster Project Assignment and formatively assessed in the mid module test during the year. The Poster Project Assignment will require students to design a poster on a natural product, and then give a viva voce explanation to a panel of judges. The viva will include synthetic and biosynthetic aspects (including stereochemistry) as well as medicinal chemistry and drug history / development.
2) Discuss advanced stereochemistry concepts including the importance of stereochemistry in the design of drugs and the resolution and the synthesis of chiral compounds. Formative assessment will be provided during workshops and the team work sessions as well as via on-line material for selected topics and the mock exam. This learning outcome will be summatively assessed in the exam as well as in the Poster Project Assignment and formatively assessed in the mid module test with 5-mark questions indicative of the style to be used in the final exam.
3) Describe the structures and properties of simple molecules of biological importance such as proteins, carbohydrates and fatty acids. Opportunities for formative assessment will be provided during workshops. This learning outcome will be summatively assessed in the exam.
4) Apply the principles of retrosynthetic analysis, chemoselectivity and protecting group strategy to devise potential routes for the synthesis of organic compounds. Opportunities for formative assessment and feedback will be provided in the group work sessions for poster preparation, while the group presentation will summatively assess this learning outcome. Questions related to this learning outcome will be included in the exam.
5) Discuss the role of SAR, organic synthesis and other approaches to drug design and drug delivery and the structure, function and mode of action of therapeutic drugs. Formative assessment will be provided during workshops and the team work sessions as well as on-line material for selected topics. This learning outcome will be summatively assessed in the exam as well as in Poster Project Assignment.
6) Contribute to team work and present the team results using key communication skills. Continuous feedback will be provided by tutors during group work sessions. Group work will be summatively assessed at the end of the poster project in a group presentation in front of a panel of judges.

Elements of Assessment

Description of Assessment Definitive UNISTATS Categories Percentage
End of year Written Exam Written Exam 60%
Poster Project Practical Exam 60%
Laboratory Experiments Including Samples Coursework 60%
Total (to equal 100%) 100%

Achieving a pass

It IS NOT a requirement that any element of assessment is passed separately in order to achieve an overall pass for the module.

Bibliography core texts

Fessenden, R. J.; Fessenden J. S. (1998), Organic Chemistry, 6th Edition, Brooks/Cole

or

Clayden, J.; Greeves, N.; Warren, S.; Wothers, P. (2012) Organic Chemistry, 2nd Edition, OUP

Patrick, G. (2009) An Introduction to Medicinal Chemistry, 4th Edition OUP

Bibliography recommended reading

Joule, J. A.; Mills, K. (2000), Heterocyclic Chemistry, 4th Edition, Blackwell/Wiley.

Sykes, P. (1986) A Guidebook to Mechanism in Organic Chemistry, 6th Edition, Longmans

Williams, D. H.; Fleming, I. (1995) Spectroscopic Methods in Organic Chemistry, 5th Edition, McGraw Hill

Warren, S. (2009) Organic Synthesis: The Disconnection Approach, 2nd Edition Wiley.

March, J. (2007) Advanced Organic Chemistry, 6th Edition Wiley.

D L Pavia, G. M. Lampman; Kriz, G. S. (2008) Introduction to Spectroscopy, 4th Edition, Brooks/Cole.

Hanson, J. (2006) Chemistry and Medicines Royal Society of Chemistry Press.

Silverman, R. (2004) The Organic Chemistry of Drug Design and Drug Action, 2nd Edition, Academic Press.

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