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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.
Question 11
What is the target for clavulanic acid?
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.
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).
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?
Question 6
The following diagram shows development of H2-
antagonists from burimamide (structure B).
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.
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.
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