1 Medicinal Chemistry 410 Exam #1 February 29, 2008 Med. Chem.

# (75 Points)

Name: Part I.

There are 50 multiple choice questions worth 1.5 points each (75 Points). Please use the Scantron Sheet provided.
1.
H NH2 H NH2

The anticancer drug illustrated below: O I reacts with DNA primarily forming an interstrand cross link. O II exhibits greater nephrotoxicity than cisplatin. Pt O III primarily forms adducts with a single strand of helical DNA. O a b c d e I only III only I and II only II and III only I, II, and III

Answer

2.
H2N

The drug illustrated below:
O S N O H CH3 N O

I is a false substrate that mimics p-aminobenzoic acid. II inhibits the De Novo synthesis of folates in bacteria. III is used to treat bacterial urinary tract infections (UTI’s).

a. b. c. d. e. 3.
H2N S N N O H CH 3 HN N SO 3 H

I only III only 1 and II only II and III only I, II, and III

Answer

The drug illustrated below has which of the following properties:

O O H 3C C CH3 C O O Na

I II III

is recognized for its effectiveness against gram (-) bacteria cross allergenicity in patents sensitive to pencillins is fully expected. is used orally.

a b c d e

I only III only I and II only II and III only I, II, and III

Answer

H2N N S N O H3C O H H N H O CH3 COOH N S I only III only I and II only II and III only I. III is an aromatase inhibitor. II. C N CO2 H2 a b c d e 7. The drug illustrated below: NH2 N O N HO P O OH N N I is associated with chain termination in the synthesis of viral DNA. II binds to the heme portion of a specific cytochrome P450. and III a b c d e 5. II. III inhibits bacterial cell wall synthesis by inhibiting penicillin binding protein ( a transpeptidase). I only III only I and II only II and III only I.2 4. is a potent antifungal agent. and III Answer The drug illustrated below: I is NOT orally active. III is resistant in viruses with a deficiency in viral thymidine kinase. Cl N Cl Answer The drug illustrated below: O CH2CH2CH2C OH I II III is too unstable for oral administration. a b c d e I only III only I and II only II and III only I. I only III only I and II only II and III only I. II is converted to a mimic of 2’-deoxyadenosine triphosphate. II. II. primarily cross-links two individual DNA strands. II is β-lactamase resistant. and III Answer . is a bifunctional alkylating agent. and III Answer The drug illustrated below: I. a b c d e 6.

the enzyme which reduces testosterone to 5α-dihydrotestosterone. N H2C N O O N N O H3CH2C OH O O The drug illustrated below: CH3 I is a mitotic spindle poison. Answer I blocks androgenic receptors. II. and III Answer The drug illustrated below: I II III I only III only I and II only II and III only I. N N N H I only III only I and II only II and III only I. a b c d e 10. and III Answer The drug illustrated below: N CH3 I is used in monotherapy (single-agent therapy) of HIV infection. blocks protein synthesis by binding to ribosomal RNA. II has been used to treat prostate cancer. II is NOT cross-resistant with nucleoside reverse transcriptase inhibitors. III inhibits 5α-reductase. and III O Answer .3 8. The drug illustrated below: a b c d e 11. II is a substrate for the efflux transporters MDR1 and BCRP. II. irreversibly inhibits the enzyme thymidylate synthetase. II. III stabilizes the cleaved complex formed from topoisomerase I and DNA. II. N NH2 N H2C NH2 OCH3 H3CO OCH3 I only III only I and II only II and III only I. and III inhibits dihydrofolate reductase in bacteria. III is a non-competitive inhibitor of reverse transcriptase. a b c d e I only III only I and II only II and III only I. a b c d e 9.

O H H S N H N N OCH3O C O O O O CH3 CH3 I only III only I and II only II and III only I. The drug illustrated below: I is leucovorin and is used in “rescue therapy”. a b c d e I only III only I and II only II and III only I. II inhibits DNA synthesis by limiting the DeNovo synthesis of thymidine. II. I CH2CH3 CH3 CH3 N CH2CH2 O a b c d e 15. II. II. III inhibits dihydofolate reductase. and III Answer The drug illustrated below: I II III is used in combination with the thymidine mimic. does cause chain termination of developing viral DNA. a b c d e 13. II is an estrogen receptor antagonist. and III Answer The drug illustrated below: O CH2OCONH2 I II III is a prodrug. is effective against RNA-containing viruses. NH2 N H HOH2C O O S N H I only III only I and II only II and III only I. and III Answer . can be administered orally. III inhibits the synthesis of estrogen. and III Answer The drug illustrated below: has been used to prevent breast cancer in high risk individuals. Zidovudine (AZT). a b c d e 14. II. is β-lactamase resistant. I only III only I and II only II and III only I.4 12.

and III Answer . II can cause hemorrhagic cystitis as a side effect. is a bifunctional alkylating agent. and III Answer The drug illustrated below: CH3 OH C CH H H HO H I is an oral contraceptive. II. I only III only I and II only II and III only I. II. II. and III Answer The drug illustrated below: I does NOT require oxidative metabolism. I only III only I and II only II and III only I. III is a bifunctional alkylating agent. and III N(CH3)2 OH NH2 OH OH O Answer The drug illustrated below is: H I II III is a bacterial protein synthesis inhibitor. but only hydrolysis to be active. a b c d e 17. OH O O a b c d e 18. a b c d e 19. is associated with hemorrhagic cystitis. II is an estrogenic steroid. The drug illustrated below: O O P N(CH CH Cl) 2 2 2 NH I II III can only be administered intravenously.5 16. II. is active orally. a b c d e I only III only I and II only II and III only I. is β-lactamase resistant. HO CH3 H I only III only I and II only II and III only I. III has a 11β-hydroxyl group.

II has been used to treat benign prostatic hyperplasia. III is associated with photosensitivity. II. III acts as a competitive inhibitor 5α-reductase activity. requires metabolic activation. and III Answer is used to treat tuberculosis. II has inhibitory activity on bacterial cell wall synthesis. III targets the enzyme DNA gyrase and converts it into a cellular poison. I only III only I and II only II and III only I. and III H3C CH3 C CH3 HN O CH3 Answer The drug illustrated below: CH3 H O N H H H H H I has been used to treat hair loss (alopecia) in males. a b c d e I only III only I and II only II and III only I. and III Answer 21. II. and III Answer . a b c d e 22.6 20. II. The drug illustrated below: O (H3C)2HCHNC CH2NHNHCH3 I II III a b c d e I only III only I and II only II and III only I. I only III only I and II only II and III only I. The drug illustrated below: O F H H N H N N OCH3 CO2H I initially blocks protein synthesis in bacteria. II. HN O N H The drug illustrated below: O F I is converted to its 2’-deoxyribosylmonophosphate. II ultimately can irreversibly bind to and inhibit thymidylate synthetase. is a monofunctional alkylating agent. a b c d e 23.

c-Kit. a b c d e 25. has an 11β-hydroxyl group. and III Answer The drug illustrated below is: I II III a b c d e is activated to an inhibitor of dihydrofolate reductase. and III O CH OH OH 2 Answer The drug illustrated below: O OCH3O H3C OH OH O NH2 O I II III acts by targeting topoisomerase II. malaria stimulates L-asparaginase in cancer therapy. The drug illustrated below is: OH O CH HO CH3 H O H H O H I II III a potent mineralocorticoid. I only III only I and II only II and III only I. and III Answer 26. II. and III Answer . II. and VEGFR (-2 & -3). II is used to treat hepatocellular carcinoma. is known to exhibit cardiac toxicity. is used in combination therapy to prevent the parasitic disease. II. among the more potent glucocorticoids. O H3C N H O O N N H N H CF 3 Cl The drug illustrated below: I is a protein tyrosine kinase inhibitor. III targets Raf kinase. a b c d e I only III only I and II only II and III only I. I only III only I and II only II and III only I. PDGF. a b c d e 27. extravasation of this agent is associated with severe necrosis at the site of infusion. II. I only III only I and II only II and III only I.7 24.

and III Answer is associated with nausea and vomiting. II. CH(CH3)2 a b c d e 29. II. F a I only b III only c I and II only d II and III only e I.8 28. II. III inhibits 14α-demethylase in the biosynthesis of ergosterol. and III The drug illustrated below: Answer I is a non-nucleoside reverse transcriptase inhibitor. is used to treat brain tumors The drug illustrated below: ClH2CH2CN H O C NCH2CH2Cl N O I II III 30. III acts as a “transition state” enzyme inhibitor. is a prodrug. The drug illustrated below: O HN H2N O C H O NH2 CH2OH N O N N I II III is a 2’deoxycytosine mimic. a I only b III only c I and II only d II and III only e I. is transformed into two different monofunctional alkylating agents. II is a HIV protease inhibtor. I only III only I and II only II and III only I. requires phosphorylation by viral thymidine kinase for activity. and III The drug illustrated below: F Answer N N N OH N N N I binds to ergosterol and disrupts the cell membrane of fungi II is used systemically. II. 31. and III Answer . a b c d e I only III only I and II only II and III only I.

II. 35. and III Answer The drug illustrated below: CH 2CH3 N H CO2 CH 3 N H N H C O H CH 2CH 3 OCOCH 3 CO 2CO3 OH I II III is lethal if administered by intrathecal injection. and III The drug illustrated below: I II III a b c d e Answer is a suicide substrate. II orally active. III a β-lactamase inhibitor. 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. Avastin® I I only III only I and II only II and III only I. HO N is an antibody that binds to the receptor for vascular endothelial growth factor. The drug illustrated below is: HO O S CH3 N O C N H2 COOH N N I a highly effective Gram (-) antibiotic. and III Answer 34.9 32. II. acts as a mitotic spindle poison by destabilizing microtubules and promoting their dissolution. I only III only I and II only II and III only I. Bevacizumab. II. a I only b III only c I and II only d II and III only e I. acts as a mitotic spindle poison by inhibiting the disassembly of microtubules. a b c d e 33. II is a humanized monoclonal antibody. is a non-competitive and an irreversible inhibitor. an antagonist for the aromatase receptor associated with stimulating estrogenic activity in mammalian breast tumor cells. II. and III Answer .

is the second most potent androgenic metabolite of testosterone. is incorporated into viral DNA. and III Answer . I only III only I and II only II and III only I. and III ultimately acts as a guanosine mimic.or T-lymphocytes. is used to increase fertility. II is the most common of childhood leukemia III is the uncontrolled growth of granulocytes. a b c d e I only III only I and II only II and III only I. III is not cross allergenic with penicillin antibiotics. is synergistic with AZT (a thymidine mimic).10 36. II. a b c d e 38. and III Answer I is uncontrolled growth of B. II. a b c d e 37. The drug illustrated below O HN HO N H O N N I II III I only III only I and II only II and III only I. II cannot form the ketal intermediate at low pH that is associated with the stomach cramping of other macrolide antibiotics. II. II. and III Answer The drug illustrated below: CH3 OH H H H OH I II III HO is a metabolite of estrogen. Acute Lymphocytic Leukemia (ALL) a b c d e 39. I only III only I and II only II and III only I. H3C N H3C HO HO H3C CH3CH2 O O CH3 CH3 O O CH3 O H3C Answer The drug illustrated below: H3C CH3 N O OCH3 CH3 OH CH3 CH3 I has limited clinical use because of its short half-life.

has an anabolic:androgenic ratio of 3:1.11 40. II. HER2. is an orally active synthetic estrogen. The drug illustrated below is: I used to prevent hemorrhagic cystitis associated with the O administration of cyclophosphoramide. The drug illustrated below: I is a monoclonal antibody used to treat metastatic breast cancers that Rituximab. I only III only I and II only II and III only I. Is used as an abortifacient. and III Answer . CD-20. III is used in the treatment of non-Hodgkin’s lymphoma that possess the membrane bound phosphoprotein. II acts as an antiangiogenic agent to prevent the production of new blood vessels. OH HO H III used to prevent renal toxicity associated with the administration of cisplatin. II. and III Answer The drug illustrated below: I II III a b c d e 42. Answer The drug illustrated below: I II III Is a potent glucocorticoid. II. HO CH3 a I only b III only c I and II only d II and III only e I. II. a I only b III only c I and II only d II and III only e I. is an aromatase inhibitor. and III O O CH3 H F O H O O O H2N 41. and III Answer 43. S N P II activated by alkaline phosphatase. a I only b III only c I and II only d II and III only e I. Rutuxin® overexpresses human epidermal growth factor 2. Is a potent mineralocorticoid.

II. and III OH O O a b c d e Answer . I only III only I and II only II and III only I. and III Answer The drug illustrated below: 45. such as CYP450 3A4. II cannot be used orally. O HS CH2 CH2 S O O Na The drug illustrated below is: I converted to its disulfide in the kidney and then rapidly eliminated in urine. Binds to mycobacterial DNA dependent RNA polymerase. III rapidly converted to its disulfide in the bloodstream.12 44. and III Answer The drug illustrated below: H N(CH3)2 OH NH2 OH OH O I rarely is associated with allergies. I only III only I and II only II and III only I. III inhibits 14α-demethylase in the biosynthesis of ergosterol. a b c d e 47. but is effective topically for Tinea infections. III can be administered orally. CH3 CH3 HO O H3CCO H3CO OH O CH3 CH3 H3C O O O CH3 O OH O NH N N N CH3 Answer The drug illustrated below is: CH3 I II III binds to ergosterol producing an antifungal effect. a I only b III only c I and II only d II and III only e I. II used to prevent hemorrhagic cystitis that is commonly associated with the administration of cyclophosphoramide. II can discolor and retard growth of developing teeth in children. II. II. known to induce cytochrome P450 enzymes. CH3 N CH3 C C C CH3 CH3 I inhibits squalene epoxidase in the synthesis of ergosterol. and III a b c d e 46. II. HO CH3 H I only III only I and II only II and III only I.

NH N H2N HOH2C N N N The drug illustrated below: I is used in combination with nucleoside reverse transcriptase inhibitors that mimic thymidine or 2’-deoxycytosine. II is a gonadotropin-releasing hormone agonists (GnRH) III is used to treat advanced prostate cancer. . and III The drug illustrated below: Answer I is an orally active peptide. The letter “Z” may be used as an answer as seldom or as often as needed. III is an entry inhibitor preventing HIV entry into non-infected human T cells. III is metabolically converted to a mimic of 2’-deoxyguanosine. II must be converted to a 5’-triphosphate to be active. II is orally active. a b c d e I only III only I and II only II and III only I. II. a I only b III only c I and II only d II and III only e I. I only III only I and II only II and III only I. II. In the space provided under the structure of each the compounds illustrated. II. write the correct CAPITALIZED letter corresponding to the choice of answers given on the bottom of the page. Provide the Generic Names for the Compounds listed on the following page. and III The drug illustrated below: Answer I binds to CCR5 and prevents interaction with gp120 acting as a chemokine receptor antagonist. and III Answer Part 2 Generic Names (9 Points).13 48. a b c d e 50. 49.

Dacarbazine T. Meropenem P.14 O CH3 OH CO2H H2N H3CO O S N O H N OCH3 N H3C N F N O H N CH3 CH3 H H H Answer HO H CH3 H H N(CH3)2 H OH NH2 OH O OH OH O O O Answer H3C HO H O H H CH3 H H S N COOH O H N H CH3 N CH3 Answer O HN O O CH3 C N CH2 N N H O H Answer H3C O H3C H3C N S N N CH3 H CH3 H N O OH N H O O S N Answer H2N N S N O H H N H OCH3O N CO2 S O CH2OCCH3 Answer Answer Na Answer 6' Answer H2NH2C O H2N NH2 NH2 O O HO HO HOCH2 HO H2N O OH Answer Answer CH3 N CH3 C C C CH3 CH3 Answer H H2N C O H H N H O HO N S CH3 CH3 COOH Answer N N N F N N F OH CH3 F Answer O H O HO O N N CH3 Answer H 3C CH3 N CH3 OH C C CH 3 H H N3 O Answer A. Betamethazone F. Terbinafine I. Doxycycline E. Ritonavir Y. Sulfadoxine Answer J. Voriconazole Z. Cefotaxime B. Etoposide C. Clavulanic acid D. Dexrazone U. None of These . Topotecan G. Oseltamivir Answer S. Tobramycin H. Mifepristone K. Amoxicillin M. Levofloxacin X. Aldosterone V. Testosterone L. Trimethoprim Q. Piperacillin W. Zidovudine N. Ribavirin R. Finasteride O.

[6S-[6α. 7-[[amino(2bromophenyl)acetyl]amino]-8-oxo-3-(1-propenyl)-. Pregna-1.0]oct-2-ene-2-carboxylic acid.7β(S*)]]- . 11β-hydroxy-6α-methyl [known as Endrysone] 2.2. Example CH3 OR H H H3C NOT H CH3 1. 5-Thia-1-azabicyclo[4.15 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.20-dione.4-diene-3.

2-amino-1. 6H-Purine-6-one. Generic Names Part 3 Nomenclature Total 75 Points 9 Points 16 Points . Multiple Choice Part 2. 6-fluoro-1-(4-fluorophenyl)-1.4-dihydro-4-oxo-7-(1piperazinyl)-. monohydrochloride [known as Sarafloxacin] N Exam Total: Part 1.9-dihydro-1-ethyl-9-[2-hydroxy-1-(fluoromethyl)ethoxy]methyl 4. 3-Quinoline carboxylic acid.16 3.

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