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Philadelphia University
Department of Pharmaceutical First semester 2011/2012
Sciences
Pharmaceutical Medicinal Chemistry-2
0511322
Final examination 15/01/2012
Lecturer: Dr. Bilal Al-Jaidi
Internal reviewer: Dr. Mwaffaq Badawneh
Faculty of Pharmacy
Student name:
Registration no.:
Question-1: Choose the most appropriate answer for all the following questions: (8 marks)
1. Regarding Mustine, the following is true:
A.
B.
C.
D.
E.
It acts as alkylating agent
The nitrogen might play a role in the mechanism of action
No role for the chlorine atom in activity
A and B
All of the above
2. Regarding Treosulfon, the following is true:
A.
B.
C.
D.
The sulfonate group is important for activity
The removal of OH group will abolish the activity
The selected carbon is the reactive part in the structure
All of the above
3. Carmustine is an anticancer agent, which of the following is
true regarding this drug:
a) Used in brain tumour because it has the reactive nitroso
group
b) The dichloroethyl group is responsible for the alkylating
activity
c) It can only form one covalent bond with DNA
d) Only a and b
e) All of the above
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4. The following is one of the carrier group added to
nitrogen mustard to enhance their absorption and cell
uptake:
A.
B.
C.
D.
E.
Amino acid
Steroid ring
Nucleic acid
Only A and B
All of the above
5. The following are DNA alkylating agents except:
A.
B.
C.
D. Only B and C
6. The following is true regarding Thiotepa
A.
B.
C.
D.
E.
Is a safe anticancer agent
Urethane group acts as a leaving group
Could form more than one bond with DNA
Chemically stable structure
All except A
7. The following could be true regarding 6-mercaptopurine:
A.
B.
C.
D.
It is active in this form, not a prodrug
Thiol group is important for activity
Inhibits Pyrimidine biosynthesis
Oxidation of pteridine ring will reduce
activity
E. Only B and C
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8. Fludarabine is used for the treatment of
chronic lymphatic leukaemia, the structure
acts as a prodrug. What is the active
compound?
A. Monophosphate
B. Diphosphate
C. Polyphosphate
D. Triphosphate
9. The following diagram is representative of a group of naturally occurring compounds
that is used in combination therapy to treat a variety of tumours, Which group of
compounds is represented by this structure:
A. Podophyllotoxins teniposide
B. Camptothecins irinotecan
C. Taxanes
D. Vinca alkaloids
10. How do Taxanes plant alkaloids work?
A. It inhibits tubulin depolymerisation
B. it inhibits tubulin polymerisation
C. It inhibits both processes
D. It inhibits neither process
11. The following group of structures is
intercalating anticancer agents, to which family
of compounds do these structures belong?
A. Podophyllotoxins
B.
Camptothecins
C. Anthracyclines
D. Bleomycins
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12. Which of the following drugs inhibits
topoisomerase II?
A.
B.
C.
D.
Uracil mustard
Daunorubicin
Cyclophosphamide
Cisplatin
13. The following structure is called lomustine and is
used in the treatment of brain tumours. Which of
the following statements is true regarding the
above structure?
A. It cannot cross the blood brain barrier.
B. It is activated by an enzymatic metabolic
reaction
C. It cannot be given orally.
D. It is both an alkylating and a carbamoylating
agent.
14. The following structure is a biosynthetic precursor
for an important enzyme cofactor required by the
enzyme thymidylate synthase: what is this cofactor
A. Folic acid
B. Dihydrofolic acid
C. Tetrahydrofolic acid
D. N5, N10-methylene tetrahydrofolic acid
15. The following structure is used in the treatment
of breast, liver and skin cancers, What is the
target for the structure
A.
B.
C.
D.
Thymidylate synthase
Dihydrofolate reductase
Adenosine deaminase
Ribonucleotide reductase
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Question-2
Identify the following structures:
Question-5: (3 marks)
Melphalan is an anti-cancer agent, answer the following questions based on its structure below:
1. It is an alkylating agent, explain?
.....................................................................................................................................................
.....................................................................................................................................................
2. Is there any role for the circled group in the pharmacokinetic/pharmacodynamic properties
of melphalan, discuss your answer?
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Question-7
Draw the messing structures in Chlorambucil synthetic scheme:
Look carefully to the illustrated structures in the table and then answer the following
questions? (22 marks)
1.
3.
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1. What is the name of compound 1................................, which region of the molecule is
involved in intercalation..........................................................................., they chelate a ferrous
ion as part of their mechanism of action, which region of the molecule is important in chelating
ions, ..................................................................................................................
............................................................................................................................................................
................................................................................................................................
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3. What is the name of compound 3................................, side effect associated with this
compound is........................................................, which can be avoided by co-administration with
........................................................., Draw its mode of action, and mention the name of
metabolite responsible for its side effect?
4. What is the name of compound 4................................, What sort of agent is it ...................
............................................., The structure is a prodrug which is converted in the body to the
active compound. Draw the steps in this activation process?
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