Chapter 8 Multiple Choice Questions

. Which of the following statements best describes drug optimisation?

The study of how drugs reach their target in the body and how the levels of a drug in the blood are affected by absorption, distribution, metabolism and excretion

The study of how drugs can be designed using molecular modelling, based on drug's pharmacophore.

The design of a synthetic route that will produce a drug cheaply and in high yield

The design and synthesis of analogues based on the structure of a lead compound in order to improve pharamacodynamic and pharrmacokinetic properties.

. Which of the following statements is true regarding the possible binding interactions of an ester?

An ester can only participate in hydrogen bonding as a hydrogen bond donor.

An ester can only participate in hydrogen bonding as a hydrogen bond acceptor.

An ester can participate in hydrogen bonding both as a hydrogen bond donor and a hydrogen bond acceptor.

An ester cannot participate in hydrogen bonding at all.

. Which of the following statements is true regarding the possible binding interactions of a secondary amide?

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

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

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

It cannot participate in hydrogen bonding at all.

. Which of the following statements is true regarding the possible binding interactions of a secondary amine?

Hydrogen bonding only

Van der Waals interactions only

Ionic bonding only

Both hydrogen bonding and ionic bonding

. What modification could you reasonably carry out on an amine to assess whether the group is important in binding a rug to a target biding site?

Convert it to an ether

Convert it to an amide

Convert it to an alkane

Convert it to an ester

. Which of the following statements is not necessarily true about analogues produced by the simplification strategy?

they adopt several conformations

they are easier to synthesise

they are cheaper to synthesise

they have less side effects

. Structure I is an antihypertensive agent which acts by inhibiting the enzyme angiotensin converting enzyme (ACE). Structure II was designed to bind to the binding site more strongly and to have greater activity.

Which of the following strategies was used in the design of structure II?

Extension

Rigidification

Use of an isostere

Simplification

. Why do many drugs containing ester functional groups have a limited duration of action?

the ester groups make the drug more polar and reduce absorption

the ester groups are susceptible to esterase enzymes

the ester groups act as steric shields and prevent drugs entering binding sites

drugs with ester groups are rapidly excreted by the kidneys

. Analogues of a lead compound can often be prepared by alkylating an amine group if it is present. Which of the following statements is false?

Amine groups are rarely involved in binding interactions with a binding site and so adding substituents is unlikely to be detrimental to binding

It is relatively easy to alkylate amine groups, either directly or via amides.

It is possible to replace an N-methyl substituent with a different substituent

Varying N-substituents can influence the pharmacokinetic properties of the drug.

. The following synthetic scheme has been used to synthesise raltegravir.

If you wanted to create a number of analogues, which substituent could be varied most efficiently using this synthesis?

The type of substituent (A) on the aromatic ring

The type of alkyl substituent (B) present

The type of heterocyclic ring (C) present

The length of the chain (D) between the amide and the aromatic ring

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