ELM7: Drug structures Flashcards

1
Q

What are optical isomers?

A

Pairs of compounds where there’s a different configuration about one or more atoms
Non superimposable
Identical physical and chemical properties
Interact differently with biological systems

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2
Q

What is a chiral centre?

A

Carbon atom with four different things bound

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3
Q

What is constitutional isomerism?

A

Molecules have different forms due to rotation of bonds

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4
Q

What is geometric isomerism/cis-trans isomerism?

A

A double bond or ring structure prevents rotation of a bond

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5
Q

How can three point binding be used in pharmacology?

A

A drug with a chiral centre has higher affinity for a target matching three points rather than 2

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6
Q

What are the three systems of classifying enantiomeric pairs?

A

+ or -
D or L
R or S

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7
Q

What is the + or - classification of enantiomeric pairs?

A

Enantiomers are identical apart from the direction they rotate polarised light in
Clockwise is +
Anticlockwise is -

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8
Q

What is used to measure the rotation of polarised light?

A

A polarimeter

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9
Q

What is the D or L classification of enantiomeric pairs?

A

Based on how much a molecule relates structurally to glyceraldehyde
D is structurally related to + glyceraldehyde
L is structurally related to - glyceraldehyde

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10
Q

What is the R or S classification of enantiomeric pairs

A

Cahn Ingold Prelog system
R right or S left

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11
Q

What are the stages of working out the classification of an enantiomer using the Cahn Ingold Prelog system?

A
  1. Find chiral centre
  2. Prioritise substituents according to atomic number
  3. Rotate molecule so the lowest priority group faces backwards
  4. Highest to lowest is clockwise then R
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12
Q

What is an example of a stereoselective interaction?

A

Noradrenaline
The R enantiomer binds to B2 adrenoceptors 45x tighter than the S enantiomer

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