Pharm PCH 222- Stereochemistry 2024.pptx

Pharmaceutical Chemistry

1. PCH 222- STEREOCHEMISTRY P. ODUMOSU 2022/2023 SESSION APRIL 2024

2. Course outline Introduction Stereochemistry Isomerism: Optical and Geometrical isomerism Physical/biological activity. R and S notation Enantiomers Properties of enantiomers Chirality Diastereoisomers Properties of diastereoisomers Medicinal application of enantiomers

3. Learning objectives Define stereochemistry Define terms used in stereochemistry Differentiate types of isomerism Explain the principle of chirality Describe the properties and medicinal applications of enantiomers

4. INTRODUCTION Many compounds have left and right-handed forms Why is it important to pharmacists? Thalidomide disaster – Late 1950’s / early 1960’s – Canada, USA, UK – Many physically handicapped children born – Malformed or no limbs (mostly arms affected)

5. Stereochemistry Defined as the study of the three-dimensional structures of molecules Knowledge is important for ; Understanding reaction mechanisms (spatial arrangement) The basis of the biological action of several drugs

6. Isomerism

7. Isomerism Two main types are known; Structural isomerism Stereoisomerism Stereoisomers are compounds in which atoms or groups of atoms are bonded in the same way but differ in their three-dimensional arrangement Two types of stereoisomers: Optical and geometrical

8. Video - Stereochemistry

9. Polarimetry

10. Cahn-Ingold - prelog Rule-Video

11. Chirality

12. Video

13. References