Medicinal Chemistry I Examination December 7, 2007 Name Med. Chem. # THERE ARE TWELVE PAGES IN THIS EXAM!
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1 Medicinal hemistry Examination December 7, 2007 ame Med. hem. # 1 TERE ARE TWELVE PAGE T EXAM! Part. 60 Points (30 Questions; 2 Points Each) elect the BET answer for each of the following. 1. The drug illustrated below: The drug illustrated below is: The drug illustrated below is : n 3 as antiemetic activity. s active as a 1 antagonist. auses sedation. s an enzyme inhibitor. an be administered iv. Binds bile acids and prevents their reabsorption. ( 3 ) Used to treat angina. Used to treat arrhythmias. Known to increase serum triglycerides. 3 3
2 4. The drug illustrated below: 2 s an α 2 -agonist (centrally-acting). Physically displaces norepinephrine from storage granules. Blocks the refilling of norepinephrine in storage granules. 5. The drug illustrated below: l. s a thiazide diuretic. s used iv to reduce blood pressure. 3 s used orally to treat insulin-induced hypoglycemia. 6. The drug illustrated below is: The drug illustrated below: 3 l 3 a. only b. only c. 1 and only d. and only e.,, and Answer s used as an antihypertensive agent. s associated with lower serum LDL. s associated with orthostatic hypotension as a side effect. s a prodrug. ncreases Lipoprotein Lipase activity in endothelial cells. A lass B antiarrhythmic agent.
3 8. The drug illustrated below: Acts as a receptor antagonist. an produce a non-productive dry cough. s an angiotensin-converting enzyme inhibitor The drug illustrated below: (3 ) 2 an cause hyperkalemia. an cause hypomagnesemia. an cause hyperuricemia The drug illustrated below: 3. s administered parenterally. 2 3 s used to treat ventricular arrhythymias. 3 2 s a lass B antiarrhythmic agent The drug illustrated below is: 3 Able to effectively block 1-receptors. An 1 -antagonist. Used to prevent motion sickness.
4 12. The drug illustrated below: 4 2 ( 2 ) 2 2 P ( 3 ) 2 2 s approximately 50% eliminated in the bile. s a cascading prodrug. s an antagonist at angiotensin receptors The drug illustrated below: s available in an iv formulation. s a potent vasodilator. s a calcium channel blocker. 14. The drug illustrated below: s used to treat allergic conjunctivitis. ncreases mucosal secretion in the stomach.. s a lass antiarrhythmic agent. 15. The drug illustrated below: s a D 2 -Agonist. s metabolized to α-methylnorepinephrine. 3 2 as been used as an antihypertensive agent.
5 The drug illustrated below: 2 Provides symptomatic relief in males with benign prostatic hyperplasia. s an α 1 -antagonist. as a short duration of action (< 2 hours) The drug illustrated below is: l 2 s a thiazide diuretic s used in the treatment of hypertension. s an angiotensin receptor antagonist. 18. The drug illustrated below: 3 3 F s used to treat Erectile Dysfunction. nhibits the enzyme MG-oA reductase. Lowers serum cholesterol. 19. The drug illustrated below: as a metabolite that is active and possesses a longer duration of action. s used to treat onn s yndrome. s an aldosterone receptor antagonist.
6 20. The drug illustrated below is: Used to treat pulmonary edema. The most potent loop diuretic. Used to treat congestive heart failure. 21. The drug illustrated below is: The drug illustrated below is: Used to treat acute congestive heart failure. A phosphodiesterase type 3 inhibitor. Administered orally to prevent congestive heart failure. s an hepatic enzyme inhibitor. s a lass B antiarrhythimc agent. s a hepatic enzyme inducer. 23. The drug illustrated below is: 3 2 Used to treat glaucoma. A carbonic anhydrase inhibitor. A thiazide diuretic.
7 24. The drug illustrated below: s activated to an electrophile at low p. Acts irreversibly. s an angiotensin receptor antagonist. 25. The drug illustrated below: l l Does not cause rebound hyptertension upon sudden withdrawal. s available as a transdermal patch. s an α 2 -agonist (entrally-acting). 26. The drug illustrated below: The drug illustrated below: s administered orally. s a lass antiarrhythmic agent. s used as a prophylactic agent. s an aldosterone antagonist. s cationic at physiological p. s a bile acid metabolite of cholesterol.
8 28. The drug illustrated below: The drug illustrated below: a s used to treat hypertension. an be administered iv as an antiarrhthymic agent. s a calcium channel antagonist. a is used to treat acute asthma attacks. is administered intravenously. is used as a prophylactic. 30. The drug illustrated below: 3 Blocks the degradation of cgmp. s a phosphodiesterase inhibitor-type s used to treat pulmonary hypertension. 2 3
9 9 Part (12 points) 1. ndicate BREFLY and PEFALLY the difference, if any, in the MEAM F AT Generic ame: 2 2 ( 3 ) ndicate BREFLY and PEFALLY the difference, if any, in the MEAM F AT Generic ame: 3. ndicate BREFLY and PEFALLY the difference, if any, in the MEAM F AT 2 l Generic ame: 2 l 2 4. ndicate BREFLY and PEFALLY the difference, if any, in the MEAM F AT Generic ame:
10 Part (12 Points) ndicate BREFLY and PEFALLY the difference, if any, in the principal MEDAL UE l Generic ame: 2. ndicate BREFLY and PEFALLY the difference, if any, in the principal MEDAL UE 2 Generic ame: 3. ndicate BREFLY and PEFALLY the difference, if any, in the principal MEDAL UE l l Generic ame: 4. ndicate BREFLY and PEFALLY the difference, if any, in the principal MEDAL UE Generic ame:
11 Part V.(16 Points) omplete the structures of the FUR following compounds 11 Draw the correct chemical structure, including stereochemistry wherever indicated. Partial credit will be given but you will lose points for incorrect chemical symbols, hydrogens missing from heteroatoms, hydrogens missing from carbons labeled, and for having too many bonds to an atom (see below for examples). Examples: ncorrect chemical symbol (-1 point each) ydrogen missing from nitrogen (-1 point) Fl n 5 bonds to carbon (- 2 points) ncorrect: Fluorobenzene Piperidine ydrogens missing from carbon chain (-1 point) orrect: F or ,2,3-Benzothiadiazine-6-sulfonamide, 3,4-dihydro-3-[(4-ethoxyphenyl)methyl]- 7-(trifluoromethyl)-, 1,1-dioxide 2. 1-Piperidinebutanol, α-[4-(2-phenyl-1-oxopropyloxy)phenyl]-4- (hydroxydiphenylmethyl)-,
12 ((1-Tetrazol-1-yl)lmethyl)-1-(4-bromophenyl)-5-(4-methylpiperazin-1-yl)-1-indole, monohydochloride 4. -[1-[()-3-ydroxy-2-methyl-1-oxopropyl]-L-prolyl]-L-alanine TERE ARE TWELVE PAGE T EXAM! Part Part Part Part V 60 points 12 points 12 points 16 points 100 Points
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