Molecules of medicinal interest Flashcards
what does organic synthesis play a key role in
development of novel phamaceutical agents
what needs to be synthesised to form a chemical library
large number of compounds
when a lead compound has been identified what happens
chemistry can be applied to optimise the features
when might further synthesis be required
to produce analogues of the lead compound to identify structure activity relationships
what 4 features need to be considered when synthesizing a drug
molecular skeleton
functional groups
substituents
chirality and asymmetric centres
what does the molecular skeleton determine
overall size and shape
why is the size and shape of the molecule important
due to it needing to be able to fit into the active site of its target
how does rigidity of the molecular skeleton affect its ability to be synthesised
more rigid harder it is to synthesize
how does rigidity of the molecular skeleton affect its activity
more rigid more active
what are functional groups involved in
binding interactions between the drug and its binding site.
stability
pharmacokinetic properties
how does the amount of substituents in a drug affect its ability to be synthesized
more substituents = harder to make
what substituents can be important in binding interactions with hydrophobic pockets
alkyl substituents
what can a chiral molecule exist as
two non superimposable mirror images called enantiomers
what might enantiomers differ in
side effects
what does chemoselective mean
reaction should take place at one specific functional group in the presence of another
what does regioselective mean
occur at one position of a functional group
What reactions do i need to learn
nucleophilic substitution reactions elimination reactions electrophilic addition reactions aromatic electrophilic substitution reactions carbonyl chemistry coupling reactions functional group transformations protection and deprotection reactions
what can carbonyl compounds react with
electrophiles at the alpha carbon under appropriate conditions
what is the reaction of a carbonyl group with electrophile useful for
preparation highly functionalised molecules
what is the anion that forms called
enolate
when an enolate is formed what can happen
react with lectrophiles to give a range of substituted derivates
what two enolates can you form
kinetic enolate
thermodynamic enolate
what is the major property of kinetic enolate
fastest
what is the major property of a thermodynamic enolate
stable
