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4/1/2019 Oxford University Press | Online Resource Centre | Chapter 13

Patrick: An Introduction to Medicinal Chemistry 6e


Chapter 13

Results
You have answered 6 out of 15 questions correctly.
Your percentage score is 40%.
Question 1
Which of the following statements best describes structure-activity relationships (SAR)?

Your answer:
b) The study of the physicochemical properties that are important to the absorption of a drug into the blood supply.
Correct answer:
c) The study of the structural features of a drug that are important to its biological activity.
Feedback:
Structure-activity relationships involve the synthesis of a series of analogues of a lead compound to discover how changes in structure
affect the biological activity. In this way, important binding groups and the drug's pharmacophore can be identified.
Page reference: 215-216

Question 2
Which of the intermolecular bonding interactions below are possible for an alcohol?

Your answer:
b) van der Waals interactions only
Correct answer:
a) Hydrogen bonding only
Feedback:
The alcohol oxygen can act as a hydrogen bond acceptor and the alcohol proton can act as a hydrogen bond donor.
Page reference: 216-217

Question 3
Which of the intermolecular bonding interactions below are possible for a primary amine?

Your answer:
b) van der Waals interactions only
Correct answer:
d) Both hydrogen bonding and ionic bonding
Feedback:
The hydrogens of an un-ionised primary amine can act as hydrogen bond donors while the nitrogen can act as a hydrogen bond acceptor. If
the amine is protonated and ionised, it can form ionic interactions. In the ionised situation, the hydrogens can still act as hydrogen bond
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donors, but the nitrogen can no longer act as a hydrogen bond acceptor.
Page reference: 218-219

Question 4
Which of the intermolecular bonding interactions below are possible for an alkene?

Your answer:
b) Van der Waals interactions only
Feedback:
The alkene group has no heteroatoms and can form neither hydrogen bonds nor ionic bonds. Van der Waals interactions are possible.
Page reference: 218

Question 5
Which of the intermolecular bonding interactions below are possible for a secondary amide?

Your answer:
a) Hydrogen bonding only
Feedback:
The carbonyl oxygen of a secondary amide group can act as a hydrogen bond acceptor while the NH proton can act as a hydrogen bond
donor. The nitrogen cannot act as a hydrogen bond acceptor since its lone pair of electrons interacts with the carbonyl group.
Page reference: 219-221

Question 6
Which of the intermolecular bonding interactions below are possible for a ketone?

Your answer:
b) van der Waals interactions only
Correct answer:
a) Hydrogen bonding only
Feedback:
The carbonyl oxygen of a ketone can act as a hydrogen bond acceptor.
Page reference: 218

Question 7
Which of the following statements is true regarding an ether?

Your answer:
b) It can only participate in hydrogen bonding as a hydrogen bond acceptor.
Feedback:
An ether consists of oxygen linked to two alkyl or aromatic groups. The oxygen can act as a hydrogen bond acceptor. There is no hydrogen
attached to oxygen and so the group cannot act as a hydrogen bond donor.
Page reference: 223

Question 8
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Which of the following statements is true regarding an alkene?

Your answer:
b) It can only participate in hydrogen bonding as a hydrogen bond acceptor.
Correct answer:
d) It cannot participate in hydrogen bonding at all.
Feedback:
The alkene functional group is a C=C double bond. There are no heteroatoms present and no hydrogens attached to heteroatoms.
Therefore, the group cannot participate in hydrogen bonding. This group can form van der Waals interactions with a hydrophobic region of a
binding site.
Page reference: 218

Question 9
Which of the following statements is true regarding a secondary amide?

Your answer:
b) It can only participate in hydrogen bonding as a hydrogen bond acceptor.
Correct answer:
c) It can participate in hydrogen bonding both as a hydrogen bond donor and a hydrogen bond acceptor.
Feedback:
The secondary amide (RNHCOR) has a carbonyl oxygen that can act as a hydrogen bond acceptor. There is also a hydrogen attached to
nitrogen which could act as a hydrogen bond donor. The nitrogen itself does not act as a hydrogen bond acceptor since its lone pair
interacts with the carbonyl group.
Page reference: 219-221

Question 10
Which of the following major aims in drug design is not related to the pharmacodynamics of a drug?

Your answer:
a) The reduction of side effects
Correct answer:
d) The maximisation of oral bioavailability
Feedback:
The aims described in options a), b), and c) can all be achieved by improving the affinity and selectivity of the drug for its target. Oral
bioavailability has nothing to do with the target, and is a pharmacokinetic issue.
Page reference: 228

Question 11

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N-Phenethylmorphine was synthesised from morphine and found to have enhanced activity.

What drug design strategy was used here?

Your answer:
a) Simplification
Correct answer:
b) Extension
Feedback:
Extension involves the addition of extra binding groups to interact with extra binding regions. This is what has been carried out here by
adding an extra aromatic ring.
Page reference: 231

Question 12
SAR shows that the important binding groups in morphine are the phenol, aromatic ring and amine. A diagram can be drawn which shows these
functional groups and their relative orientations. What is the term for this?

Your answer:
b) Pharmacokinetics
Correct answer:
d) Pharmacophore
Feedback:
A pharmacophore indicates the important binding groups and their relative positions. Pharmacodynamics is the study of how a drug
interacts with its target binding site. Pharmacokinetics is the study of how a drug is absorbed, distributed, metabolised and excreted in the
body. A chromophore is a conjugated unsaturated system responsible for the colour in coloured compounds.
Page reference: 227-228

Question 13
It is common practice to vary the length and size of alkyl groups when making analogues of a lead compound. Which of the following statements
is not true?

Your answer:
c) Increasing the chain length or size of an alkyl group increases activity and selectivity by stabilising the analogue.
Feedback:
There is no obvious reason why an increase in the length or size of an alkyl group should stabilise a molecule, or why increased stability
should lead to higher activity and selectivity.
Page reference: 228-229

Question 14
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4/1/2019 Oxford University Press | Online Resource Centre | Chapter 13

Which of the following is not true of analogues produced by a rigidification strategy?

Your answer:
b) They are easier to synthesise.
Feedback:
In general, more rigid molecules tend to be more complex and more difficult to synthesise. The other statements are true since rigid
molecules retaining the active conformation are more likely to fit their target binding site and less likely to form the active conformations
recognised by the binding sites of other targets.
Page reference: 239-241

Question 15
Structure (I) has a highly flexible side chain.

Which of the following statements is true?

Your answer:
b) A flexible molecule is more likely to adopt conformations that will bind to different targets, resulting in side effects.
Feedback:
Option b) is correct. A flexible molecule can adopt several conformations, and this increases the chances of it interacting with a variety of
targets, resulting in side effects.
Option a) is wrong since a flexible molecule is less likely to be in its active conformation, resulting in decreased activity.
Option c) is correct in so far as a flexible molecule may be able to bind in different binding modes to the one target, but this is more likely to
result in decreased activity.
Option d) is wrong since a flexible molecule is less likely to show target selectivity.
Page reference: 239

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