1

Medicinal Chemistry 410 Exam #1

February 29, 2008
Name: Med. Chem. #

Part I. (75 Points)

There are 50 multiple choice questions worth 1.5 points each (75 Points).
Please use the Scantron Sheet provided.

1. The anticancer drug illustrated below:

H
NH2
O I reacts with DNA primarily forming an interstrand cross link.
O
Pt II exhibits greater nephrotoxicity than cisplatin.
NH2 O
O III primarily forms adducts with a single strand of helical DNA.
H
a I only
b III only
c I and II only
d II and III only
e I, II, and III Answer

2. The drug illustrated below:

CH3 I is a false substrate that mimics p-aminobenzoic acid.
O
H2N S N II inhibits the De Novo synthesis of folates in bacteria.
O
O H N III is used to treat bacterial urinary tract infections (UTI’s).
a. I only
b. III only
c. 1 and II only
d. II and III only
e. I, II, and III Answer

3. The drug illustrated below has which of the following properties:

H2N
N O
S H CH 3
HN H I is recognized for its effectiveness against gram (-) bacteria
N
O O
N II cross allergenicity in patents sensitive to pencillins is fully expected.
SO 3
III is used orally.
H 3C C CH3
C O
O
Na

a I only
b III only
c I and II only
d II and III only
e I, II, and III Answer
 2
4. The drug illustrated below:
NH2

N N I is associated with chain termination in the synthesis of viral DNA.

II is converted to a mimic of 2’-deoxyadenosine triphosphate.
O N N III is resistant in viruses with a deficiency in viral thymidine kinase.
HO P O
OH
a I only
b III only
c I and II only
d II and III only
e I, II, and III Answer

5. The drug illustrated below:

Cl
O I is too unstable for oral administration.
N CH2CH2CH2C OH II primarily cross-links two individual DNA strands.
III is a bifunctional alkylating agent.
Cl
a I only
b III only
c I and II only
d II and III only
e I, II, and III Answer

6. The drug illustrated below:

H2N
N O
S H H I is NOT orally active.
S
N II is β-lactamase resistant.
H
N N
C N
III inhibits bacterial cell wall synthesis by inhibiting
O O
CH3 CO2 H2
penicillin binding protein ( a transpeptidase).
H3C
COOH
a I only
b III only
c I and II only
d II and III only
e I, II, and III Answer

7. The drug illustrated below:

I. is a potent antifungal agent.

II binds to the heme portion of a specific cytochrome P450.
III is an aromatase inhibitor.

a I only
b III only
c I and II only
d II and III only
e I, II, and III Answer
 3
8. The drug illustrated below:
N CH3
H2C
N O I is a mitotic spindle poison.
O
O
N II is a substrate for the efflux transporters MDR1 and BCRP.
N
III stabilizes the cleaved complex formed from topoisomerase I and DNA.
O
H3CH2C
OH O
a I only
b III only
c I and II only
d II and III only
e I, II, and III Answer
9. The drug illustrated below:
NH2
N
N
I inhibits dihydrofolate reductase in bacteria.
H2C NH2
II irreversibly inhibits the enzyme thymidylate synthetase.
OCH3 III blocks protein synthesis by binding to ribosomal RNA.
H3CO OCH3
a I only
b III only
c I and II only
d II and III only
e I, II, and III Answer

10. The drug illustrated below:

I blocks androgenic receptors.
II has been used to treat prostate cancer.
III inhibits 5α-reductase, the enzyme which reduces
testosterone to 5α-dihydrotestosterone.

a I only
b III only
c I and II only
d II and III only
e I, II, and III Answer

11. The drug illustrated below:

N N
N I is used in monotherapy (single-agent therapy) of HIV infection.
II is NOT cross-resistant with nucleoside reverse transcriptase inhibitors.
N III is a non-competitive inhibitor of reverse transcriptase.
CH3
O H
a I only
b III only
c I and II only
d II and III only
e I, II, and III Answer
 4
12. The drug illustrated below:
I is leucovorin and is used in “rescue therapy”.
II inhibits DNA synthesis by limiting the DeNovo synthesis
of thymidine.
III inhibits dihydofolate reductase.

a I only
b III only
c I and II only
d II and III only
e I, II, and III Answer

13. The drug illustrated below:

O O
H H
N S
H
N
OCH3O
N
CH2OCONH2
I is a prodrug.
C O II is β-lactamase resistant.
O
III can be administered orally.
O CH3

O CH3

a I only
b III only
c I and II only
d II and III only
e I, II, and III Answer

14. The drug illustrated below:

I has been used to prevent breast cancer in high risk

CH2CH3 individuals.
CH3
II is an estrogen receptor antagonist.
N CH2CH2 O
CH3 III inhibits the synthesis of estrogen.
a I only
b III only
c I and II only
d II and III only
e I, II, and III Answer

15. The drug illustrated below:

NH2

N I is used in combination with the thymidine mimic, Zidovudine (AZT).

O N II does cause chain termination of developing viral DNA.
H O H III is effective against RNA-containing viruses.
HOH2C
S
a I only
b III only
c I and II only
d II and III only
e I, II, and III Answer
 5
16. The drug illustrated below:
O
O I can only be administered intravenously.
P N(CH CH Cl)
2 2 2 II is a bifunctional alkylating agent.
NH III is associated with hemorrhagic cystitis.
a I only
b III only
c I and II only
d II and III only
e I, II, and III Answer

17. The drug illustrated below is:

HO CH3 H
N(CH3)2
H
OH I is a bacterial protein synthesis inhibitor.
NH2
II is active orally.
OH III is β-lactamase resistant.
OH O OH O O
a I only
b III only
c I and II only
d II and III only
e I, II, and III Answer

18. The drug illustrated below:

CH3 OH

H
C CH I is an oral contraceptive.
II is an estrogenic steroid.
H H III has a 11β-hydroxyl group.
HO
a I only
b III only
c I and II only
d II and III only
e I, II, and III Answer

19. The drug illustrated below:

I does NOT require oxidative metabolism, but only hydrolysis to be active.

II can cause hemorrhagic cystitis as a side effect.
III is a bifunctional alkylating agent.

a I only
b III only
c I and II only
d II and III only
e I, II, and III Answer
 6
20. The drug illustrated below:
O
HN F I is converted to its 2’-deoxyribosylmonophosphate.
O II ultimately can irreversibly bind to and inhibit thymidylate synthetase.
N III is associated with photosensitivity.
H
a I only
b III only
c I and II only
d II and III only
e I, II, and III Answer

21. The drug illustrated below:

O
F CO2H I initially blocks protein synthesis in bacteria.
II has inhibitory activity on bacterial cell wall synthesis.
H H
N N N III targets the enzyme DNA gyrase and converts it into a
OCH3 cellular poison.
H
a I only
b III only
c I and II only
d II and III only
e I, II, and III Answer

22. The drug illustrated below:

H3C CH3
C CH3
HN
CH3 O I has been used to treat hair loss (alopecia) in males.
CH3 H
H II has been used to treat benign prostatic hyperplasia.
III acts as a competitive inhibitor 5α-reductase activity.
H H
O N
H H
a I only
b III only
c I and II only
d II and III only
e I, II, and III Answer

23. The drug illustrated below:

O I is used to treat tuberculosis.
(H3C)2HCHNC CH2NHNHCH3 II is a monofunctional alkylating agent.
III requires metabolic activation.
a I only
b III only
c I and II only
d II and III only
e I, II, and III Answer
 7
24. The drug illustrated below:
O
H3C
N
O Cl I is a protein tyrosine kinase inhibitor.
O
H
N II is used to treat hepatocellular carcinoma.
N N CF 3 III targets Raf kinase, PDGF, c-Kit, and VEGFR (-2 & -3).
H H
a I only
b III only
c I and II only
d II and III only
e I, II, and III Answer

25. The drug illustrated below is:

I is activated to an inhibitor of dihydrofolate reductase.

II is used in combination therapy to prevent the parasitic disease, malaria
III stimulates L-asparaginase in cancer therapy.

a I only
b III only
c I and II only
d II and III only
e I, II, and III Answer

26. The drug illustrated below is:

OH
O
CH O I a potent mineralocorticoid.
HO
CH3 H
H II has an 11β-hydroxyl group.
III among the more potent glucocorticoids.
H H
O
a I only
b III only
c I and II only
d II and III only
e I, II, and III Answer

27. The drug illustrated below:

O O

CH OH
OH 2 I acts by targeting topoisomerase II.
OCH3O OH
II is known to exhibit cardiac toxicity.
O
III extravasation of this agent is associated with severe
H3C
O necrosis at the site of infusion.
NH2
OH
a I only
b III only
c I and II only
d II and III only
e I, II, and III Answer
 8
28. The drug illustrated below:
O

HN N

H2N N N I is a 2’deoxycytosine mimic.

O II is a prodrug.
O C
O III requires phosphorylation by viral thymidine kinase for activity.
CH2OH
NH2
H
CH(CH3)2
a I only
b III only
c I and II only
d II and III only
e I, II, and III Answer

29. The drug illustrated below:

O I is associated with nausea and vomiting.
ClH2CH2CN C NCH2CH2Cl II is transformed into two different
H N O monofunctional alkylating agents.
III is used to treat brain tumors
a I only
b III only
c I and II only
d II and III only
e I, II, and III Answer
30. The drug illustrated below:
F

F I binds to ergosterol and disrupts the cell membrane of fungi

II is used systemically.
OH
N N III inhibits 14α-demethylase in the biosynthesis of ergosterol.
N N
N N
a I only
b III only
c I and II only
d II and III only
e I, II, and III Answer
31. The drug illustrated below:

I is a non-nucleoside reverse transcriptase inhibitor.

II is a HIV protease inhibtor.
III acts as a “transition state” enzyme inhibitor.

a I only
b III only
c I and II only
d II and III only
e I, II, and III Answer
 9
32. The drug illustrated below is:
HO O
S CH3 I a highly effective Gram (-) antibiotic.
N C N
N
N
II orally active.
O H2 III a β-lactamase inhibitor.
COOH
a I only
b III only
c I and II only
d II and III only
e I, II, and III Answer
33.
Bevacizumab, is an antibody that binds to the receptor for vascular
I
Avastin® endothelial growth factor.
II is a humanized monoclonal antibody.
III prevents the vascularization (endothelial cell growth) that is
associated with tumor growth
a I only
b III only
c I and II only
d II and III only
e I, II, and III Answer
34. The drug illustrated below:
HO
CH 2CH3

I is lethal if administered by intrathecal injection.

CO2 CH 3 II acts as a mitotic spindle poison by destabilizing
N
H N
microtubules and promoting their dissolution.
CH 2CH 3 III acts as a mitotic spindle poison by inhibiting the
H OCOCH 3
CO 2CO3 disassembly of microtubules.
N H OH
C O
H
a I only
b III only
c I and II only
d II and III only
e I, II, and III Answer
35. The drug illustrated below:
I is a suicide substrate.
II is a non-competitive and an irreversible inhibitor.
III an antagonist for the aromatase receptor associated with
stimulating estrogenic activity in mammalian breast tumor cells.
a I only
b III only
c I and II only
d II and III only
e I, II, and III Answer
 10
36. The drug illustrated below
O

HN N I ultimately acts as a guanosine mimic.

N
II is incorporated into viral DNA.
N
HO O III is synergistic with AZT (a thymidine mimic).
H
a I only
b III only
c I and II only
d II and III only
e I, II, and III Answer

37. The drug illustrated below:

CH3
H3C CH3
N
H3C N
H3C CH3
O
CH3 I has limited clinical use because of its short half-life.
HO
HO
O II cannot form the ketal intermediate at low pH that is associated with
H3C CH3 OCH3 the stomach cramping of other macrolide antibiotics.
O
CH3CH2 O
CH3
III is not cross allergenic with penicillin antibiotics.
CH3
O O OH
H3C
a I only
b III only
c I and II only
d II and III only
e I, II, and III Answer

38.
Acute
I is uncontrolled growth of B- or T-lymphocytes.
Lymphocytic
II is the most common of childhood leukemia
Leukemia (ALL)
III is the uncontrolled growth of granulocytes.
a I only
b III only
c I and II only
d II and III only
e I, II, and III Answer

39. The drug illustrated below:

CH3 OH
I is a metabolite of estrogen.
H OH II is used to increase fertility.
III is the second most potent androgenic metabolite
H H of testosterone.
HO
a I only
b III only
c I and II only
d II and III only
e I, II, and III Answer
 11

40. The drug illustrated below is:

I used to prevent hemorrhagic cystitis associated with the
S
O administration of cyclophosphoramide.
H2N N P
OH
II activated by alkaline phosphatase.
H HO III used to prevent renal toxicity associated with the
administration of cisplatin.
a I only
b III only
c I and II only
d II and III only
e I, II, and III Answer

41. The drug illustrated below:

I has an anabolic:androgenic ratio of 3:1.

II is an orally active synthetic estrogen.
III is an aromatase inhibitor.

a I only
b III only
c I and II only
d II and III only
e I, II, and III Answer

42. The drug illustrated below:

O
O

O
I Is a potent glucocorticoid.
CH3
HO O II Is a potent mineralocorticoid.
CH3 H
O III Is used as an abortifacient.
F H
O
a I only
b III only
c I and II only
d II and III only
e I, II, and III Answer
43. The drug illustrated below:
Rituximab, I is a monoclonal antibody used to treat metastatic breast cancers that
Rutuxin® overexpresses human epidermal growth factor 2, HER2.
II acts as an antiangiogenic agent to prevent the production of new blood vessels.
III is used in the treatment of non-Hodgkin’s lymphoma that possess the
membrane bound phosphoprotein, CD-20.
a I only
b III only
c I and II only
d II and III only
e I, II, and III Answer
 12
44. The drug illustrated below is:
O I converted to its disulfide in the kidney and then rapidly eliminated in urine.
HS CH2 CH2 S O II used to prevent hemorrhagic cystitis that is commonly associated with the
O Na administration of cyclophosphoramide.
III rapidly converted to its disulfide in the bloodstream.
a I only
b III only
c I and II only
d II and III only
e I, II, and III Answer

45. The drug illustrated below:

CH3 CH3
N C C C CH3 I inhibits squalene epoxidase in the synthesis of ergosterol.
CH3 II cannot be used orally, but is effective topically for Tinea infections.
III inhibits 14α-demethylase in the biosynthesis of ergosterol.

a I only
b III only
c I and II only
d II and III only
e I, II, and III Answer

46. The drug illustrated below is:

CH3 CH3
HO
O
H3CCO OH O CH3
CH3
H3CO CH3
I binds to ergosterol producing an antifungal effect.
OH O II known to induce cytochrome P450 enzymes, such as CYP450 3A4.
H3C NH
III Binds to mycobacterial DNA dependent RNA polymerase.
O O N N N CH3
O
O
CH3
a I only
b III only
c I and II only
d II and III only
e I, II, and III Answer

47. The drug illustrated below:

HO CH3 H
N(CH3)2
H
OH I rarely is associated with allergies.
NH2
II can discolor and retard growth of developing teeth in children.
OH
III can be administered orally.
OH O OH O O
a I only
b III only
c I and II only
d II and III only
e I, II, and III Answer
 13
48. The drug illustrated below:
NH
N I is used in combination with nucleoside reverse transcriptase inhibitors that mimic
N
thymidine or 2’-deoxycytosine.
H2N N N II must be converted to a 5’-triphosphate to be active.
HOH2C
III is metabolically converted to a mimic of 2’-deoxyguanosine.

a I only
b III only
c I and II only
d II and III only
e I, II, and III Answer
49. The drug illustrated below:

I is an orally active peptide.

II is a gonadotropin-releasing hormone agonists (GnRH)
III is used to treat advanced prostate cancer.

a I only
b III only
c I and II only
d II and III only
e I, II, and III Answer

50. The drug illustrated below:

I binds to CCR5 and prevents interaction with gp120 acting as a chemokine

receptor antagonist.
II is orally active.
III is an entry inhibitor preventing HIV entry into non-infected human T cells.

a I only
b III only
c I and II only
d II and III only
e I, II, and III Answer

Part 2 Generic Names (9 Points). Provide the Generic Names for the Compounds listed on
the following page. In the space provided under the structure of each the compounds
illustrated, write the correct CAPITALIZED letter corresponding to the choice of answers
given on the bottom of the page. The letter “Z” may be used as an answer as seldom or as
often as needed.
 14
O CH3 OH
F CO2H
H3CO OCH3
O CH3 H
N N
H2N S N N
N O CH3 H H
O H N H3C H O
Answer Answer Answer
HO O
H CH3 H H N(CH3)2 H
CH3
H O CH3
OH H3C H H CH3 N HN N CH2 C
N
O
HO H H CH3
NH2 H N
H S O H
OH N N
OH O OH O O O H O
COOH
Answer Answer
Answer
H2N
N O
H3C CH3 O H H
O S
H S N S
H3C N N N O
N N H O
OH H N N N
H3C S CH3 H O
OCH3O CH2OCCH3
CO2
Na
Answer Answer
Answer
6'
H2NH2C
O
H2N
HO
NH2 NH2
O

O
HO

HOCH2
O
HO OH

H2N
Answer
Answer Answer
H O
CH3 H H
CH3 H2N C N S CH3
N C C C CH3 H
CH3 N CH3
O
COOH
HO
Answer Answer Answer
N O CH3
N H CH3 N
N H 3C
N
OH CH3 CH3 OH
O N C C CH 3
F F O H
HO
N H
N N3 O
F
Answer Answer
Answer
A. Cefotaxime J. Mifepristone S. Dacarbazine
B. Etoposide K. Testosterone T. Dexrazone
C. Clavulanic acid L. Amoxicillin U. Aldosterone
D. Doxycycline M. Zidovudine V. Piperacillin
E. Betamethazone N. Finasteride W. Levofloxacin
F. Topotecan O. Meropenem X. Ritonavir
G. Tobramycin P. Trimethoprim Y. Voriconazole
H. Terbinafine Q. Ribavirin Z. None of These
I. Sulfadoxine R. Oseltamivir
 15
Part 3 Nomenclature 16 Points.
When using the basic templates provided insert all unsaturation as required and specify the
orientation of all functionality or hydrogen atoms by using BOLD lines/wedges or HASHED
lines/wedges.

Example

H3C
CH3 CH3
OR NOT

H H H

1. Pregna-1,4-diene-3,20-dione, 11β-hydroxy-6α-methyl
[known as Endrysone]

2. 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 7-[[amino(2-

bromophenyl)acetyl]amino]-8-oxo-3-(1-propenyl)-, [6S-[6α,7β(S*)]]-
 16
3. 6H-Purine-6-one, 2-amino-1,9-dihydro-1-ethyl-9-[2-hydroxy-1-(fluoromethyl)ethoxy]methyl

4. 3-Quinoline carboxylic acid, 6-fluoro-1-(4-fluorophenyl)-1,4-dihydro-4-oxo-7-(1-

piperazinyl)-, monohydrochloride
[known as Sarafloxacin]

Exam Total:
Part 1. Multiple Choice 75 Points

Part 2. Generic Names 9 Points

Part 3 Nomenclature 16 Points

Total