Patrick: An Introduction to Medicinal Chemistry 5e

Chapter 19: Multiple choice questions and answers

Instructions
Answer the following questions and then press 'Submit' to
get your score.
Question 1
Which of the following statements is untrue?
a) A bacterial cell is prokaryotic whereas an animal cell
is eukaryotic.
b) A bacterial cell has a cell wall whereas an animal cell
does not.
c) Bacterial and animal cells both have a well-defined
nucleus.
d) Bacteria may contain enzymes that are not present
in animal cells.
Question 2
Which of the following is the general mechanism of action
for erythromycin?
a) Inhibition of a metabolic enzyme
b) Inhibition of cell wall synthesis
c) Disruption of protein synthesis
d) Inhibition of nucleic acid transcription and replication
Question 3
The following general structure is representative of
sulphonamides. Which of the following statements is true
for active sulphonamides?

a) R1 can be H or an alkyl group

 b) R2 must be hydrogen
c) The aromatic ring is essential
d) The sulphonamide functional group can be replaced
with an ester
Question 4
Which of the following statements is true regarding the
properties of benzylpenicillin?
a) It is a bacteriostatic agent.
b) It is active over a wide range of bacterial species.
c) It is resistant to β-lactamases.
d) Certain individuals may have an allergic response to
it.
Question 5
What crucial feature of a penicillin is involved in its
mechanism of action?
a) Carboxylic acid
b) β-lactam ring
c) Acyl side chain
d) Thiazolidine ring
Question 6
What reaction is catalysed by a β-lactamase enzyme?
a) The final cross-linking reaction to form the bacterial
cell wall
b) The hydrolysis of the acyl side chain from penicillin
structures
c) The hydrolysis of the four-membered ring present in
penicillins
d) The biosynthesis of the penicillin structure from the
amino acids valine and cysteine
Question 7
The following structure (methicillin) was an important
penicillin that was introduced in the 1960s to counter the
threat of penicillin-resistant strains of S. aureus.

Which of the following statements is true regarding the

above structure?
a) There is no electron withdrawing group on the side
chain, and so it is acid sensitive.
b) It can be taken orally.
c) It is more active than penicillin G.
d) It has a broader spectrum of activity compared to
penicillin G.
Question 8
Which of the following statements is accurate in explaining
why Gram negative bacteria are generally more resistant
to penicillins than Gram positive bacteria?
a) Gram negative bacteria have a thicker cell wall
b) Gram negative bacteria have an outer hydrophilic
membrane that acts as an extra barrier
c) Gram negative bacteria can concentrate β-lactamase
enzymes in the periplasmic space
 d) Gram negative bacteria produce smaller quantities of
transpeptidase enzyme

Question 9
What role does the acetoxy group at the 3-position of
cephalosporins have in enhancing antibacterial activity?
a) It acts as a steric shield and masks enzymatic attack
at the β-lactam ring.
b) It acts as a good leaving group when the β-lactam
ring is opened.
c) It takes part in a transesterification reaction with the
carboxylic acid group at position 4.
d) It increases the reactivity of the β-lactam ring by
neighbouring group participation.
Question 10
The following structure (cefalexin) is a first generation
cephalosporin.

Which of the following statements is true for the methyl

substituent at position 3?
 a) It is a good leaving group
b) It is generally good for activity
c) It is good for oral activity
d) It acts as a steric shield

Question 11
What is the target for clavulanic acid?

a) The transpeptidase enzyme

b) L-ala racemase
c) β-lactamase
d) Penicillin acylase

Question 12
Which of the following antibiotics is a macrolide?
a) Chloramphenicol
b) Doxycycline
c) Erythromycin
d) Streptomycin
Question 13
Which of the following antibiotics is a tetracycline?
a) Chloramphenicol
 b) Doxycycline
c) Erythromycin
d) Streptomycin

Question 14
Which of the following antibiotics is responsible for Gray
Baby Syndrome?

a) Chloramphenicol
b) Doxycycline
c) Erythromycin
d) Streptomycin
Question 15
The following structure is a synthetic antibacterial agent.

To which group of compounds does the structure belong?

a) Aminoacridines
b) Aminoglycosides
c) Fluoroquinolones
d) Tetracyclines
Patrick: An Introduction to Medicinal Chemistry 5e
Chapter 25: Multiple choice questions and answers
Instructions
Answer the following questions and then press 'Submit' to
get your score.
Question 1
To what extent are the three nitrogens of histamine
ionised at blood pH?
a) all three nitrogens are fully ionised
b) all three nitrogens are not ionised at all
c) the side chain nitrogen is fully ionised and the
heterocyclic nitrogens are not ionised
d) the side chain nitrogen and one of the heterocyclic
nitrogens are fully ionised
Question 2
Three binding regions were proposed to be present in the
binding site of the H2 receptor. Which of the following
statements is incorrect?
a) There is a binding region for the imidazole ring of
histamine analogues which is common for agonists and
antagonists.
b) There is a binding region which interacts ionically
with the α-nitrogen of histamine and results in agonist
activity.
 c) There is a binding region further away from the
imidazole ring that produces an antagonist effect if
occupied.
d) The α-nitrogen of histamine can only bind to the
agonist binding region while the guanyl group of Nα-
guanylhistamine can only bind to the antagonist binding
region.

Question 3
The following structures show some of the important
molecules leading to the discovery of burimamide (B).

What strategy was used in developing burimamide from

SK&F 91581?

a) extension
b) chain extension
c) substituent variation
d) isosteric replacement
Question 4
The following structures show some of the important
molecules leading to the discovery of burimamide (B).
Which of the following statements concerning burimamide
is untrue?

a) it established the existence of H2-receptors

b) it was a good antagonist at H2 receptors with only weak
partial agonist activity
c) it inhibited gastric acid release from parietal cells
d) it indicated that binding to the antagonist binding region
involved hydrogen bonding and not ionic bonding
Question 5
The following diagram shows development of H2-
antagonists from burimamide (structure B).

A sulphur atom was inserted into the side chain of

structure C. What effect did this change have?
a) it introduced an extra binding interaction
 b) it stabilised the molecule
c) it increased the percentage population of the active
heterocyclic tautomer
d) it prevented ionisation of the terminal functional
group

Question 6
The following diagram shows development of H2-
antagonists from burimamide (structure B).

What was the rationale for the introduction of the coloured

methyl group?
 a) to block metabolism at that region of the heterocyclic
ring
b) to introduce a group which would be metabolised in a
predictable fashion
c) to introduce an electron withdrawing group on the
heterocyclic ring to reduce the chance of ionisation
d) to introduce an electron donating group on the
heterocyclic ring to favour the active tautomer

Question 7
The following diagram shows development of H2-
antagonists from burimamide (structure B).
Why was the thiourea functional group in structure D changed
to a guanidine group in structure E?
a) To introduce a basic group which could ionise and allow
ionic interactions with the binding region.
b) To replace an unnatural functional group with a
naturally occurring group in order to reduce side effects.
c) To increase the number of hydrogen bond donors
present to acquire extra binding interactions.
d) To change the geometry and stereochemistry of the
functional group such that it fitted the binding region more
closely.

Question 8
The following diagram shows development of H2-
antagonists from burimamide (structure B).
Why was the cyanide group introduced into structure F
(cimetidine)?
a) It is an electron donating group and increases the
basicity of the functional group such that it protonates and
becomes ionised.
b) It is an electron withdrawing group and increases the
basicity of the functional group such that it protonates and
becomes ionised.
c) It is an electron donating group and decreases the
basicity of the functional group such that it does not
become protonated and remains un-ionised.
d) It is an electron withdrawing group and decreases
the basicity of the functional group such that it does not
become protonated and remains un-ionised.

Question 9
Two regions of cimetidine are susceptible to metabolism.
Which regions?

a) A and B
b) A and C
c) B and D
d) A and D
Question 10
The following diagram shows various conformations for
the cyanoguanidine group of cimetidine.

Two of these conformations were found to be disfavoured.

Which ones and what was the implication of this for
receptor binding?

a) EZ and ZE. It proved the chelation theory of

hydrogen bonding.
b) EZ and ZZ. It established that there was only one
hydrogen bonding interaction with the receptor in this
region.
c) EE and ZZ. It established that there were two
hydrogen bonding interactions to different groups within
the same binding region.
d) EE and ZE. No conclusions could be drawn.

Question 11
Once activated, the proton pump inhibitors bind to
exposed amino acids in the proton pump. Which amino
acid is involved?

a) serine
b) cysteine
c) lysine
d) histidine
Question 12
The following mechanism shows how proton pump
inhibitors are activated. Which arrow is incorrect?

a) A
b) B
c) C
d) D

Question 13
Omeprazole is an important proton pump inhibitor.

Which region is prone to metabolism?

a) A
 b) B
c) C
d) D
Question 14
Which microorganism has been associated with the
appearance of ulcers?
a) Eschericia coli
b) Staphylococcus aureus
c) Enterococcus faecalis
d) Helicobacter pylori
Question 15
What bacterial enzyme aids the survival of Helicobacter
pylori in the stomach?
a) carbonic anhydrase
b) β-lactamase
c) urease
d) transpeptidase