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Patrick: An Introduction to Medicinal Chemistry 4e

Chapter 13

Instructions

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Question 1

Which of the following statements best describes structure-activity relationships (SAR)?

a) The study of which functional groups are important to the chemical reactivity of the drug.

b) The study of the physicochemical properties that are important to the absorption of a drug into the blood supply.

c) The study of the structural features of a drug that are important to its biological activity.

d) The study of the structural features of a drug that are important to its chemical stability.

Question 2

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

a) Hydrogen bonding only.

b) Van der Waals interactions only.

c) Ionic bonding only.

d) Both hydrogen bonding and ionic bonding.

Question 3

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

a) Hydrogen bonding only.

b) van der Waals interactions only.

c) Ionic bonding only.

d) Both hydrogen bonding and ionic bonding.

Question 4

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

a) Hydrogen bonding only.

b) Van der Waals interactions only.

c) Ionic bonding only.

d) Both hydrogen bonding and ionic bonding.

Question 5

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

a) Hydrogen bonding only.

b) Van der Waals interactions only.

c) Ionic bonding only.

d) Both hydrogen bonding and ionic bonding.

Question 6

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

a) Hydrogen bonding only.

b) Van der Waals interactions only.

c) Ionic bonding only.

d) Both hydrogen bonding and ionic bonding.

Question 7

Which of the following statements is true regarding an ether?

a) It can only participate in hydrogen bonding as a hydrogen bond donor.

b) It can only participate in hydrogen bonding as a hydrogen bond acceptor.

c) It can participate in hydrogen bonding both as a hydrogen bond donor and a hydrogen bond acceptor.

d) It cannot participate in hydrogen bonding at all.

Question 8

Which of the following statements is true regarding an alkene?

a) It can only participate in hydrogen bonding as a hydrogen bond donor.

b) It can only participate in hydrogen bonding as a hydrogen bond acceptor.

c) It can participate in hydrogen bonding both as a hydrogen bond donor and a hydrogen bond acceptor.

d) It cannot participate in hydrogen bonding at all.

Question 9

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

a) It can only participate in hydrogen bonding as a hydrogen bond donor.

b) It can only participate in hydrogen bonding as a hydrogen bond acceptor.

c) It can participate in hydrogen bonding both as a hydrogen bond donor and a hydrogen bond acceptor.

d) It cannot participate in hydrogen bonding at all.

Question 10

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

a) The reduction of side effects.

b) The maximisation of activity.

c) The reduction of toxicity.

d) The maximisation of oral bioavailability.

Question 11

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

What drug design strategy was used here?

a) Simplification

b) Extension

c) Rigidification

d) Conformational blocker

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?

a) Pharmacodynamics

b) Pharmacokinetics

c) Chromophore

d) Pharmacophore

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?

a) Replacing a straight chain alkyl group with a branched alkyl group may increase activity by filling up a hydrophobic pocket and increasing van der Waals interactions.

b) Increasing the chain length or size of an alkyl group may increase target selectivity if one target binding site is more spacious than another.

c) Increasing the chain length or size of an alkyl group increases activity and selectivity by stabilising the analogue.

d) Increasing the chain length of an alkyl group may increase activity by leading to better van der Waals interactions with a hydrophobic region of the binding site.

Question 14

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

a) They have a smaller number of conformations.

b) They are easier to synthesise.

c) They are likely to be more selective.

d) They are likely to be more active.

Question 15

Structure (I) has a highly flexible side chain.

Which of the following statements is true?

a) A flexible molecule is more likely to be in its active conformation when it approaches its target binding site. This results in increased activity.

b) A flexible molecule is more likely to adopt conformations that will bind to different targets, resulting in side effects.

c) A flexible molecule may be able to bind to its target binding site in different binding modes, resulting in an increase in activity.

d) A flexible molecule is more likely to show target selectivity.

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