MedChem403 Exam1 2000 - F Hour Examination L 'gls 0‘ ' II...

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Unformatted text preview: F Hour Examination L 'gls 0‘ ' II A] Kl (40) =- {,e Fcbmrymooo m k: inuM HI N'r (40) Write nearly. Confine your anSwers to the space provided. I ' TOTAL (10b) 1- “UPON” l {1' in Corvch chucks, bf ‘15" (come WV“st {.7 in A. (8 points) In the enzymatic decarboxylation of L-DOPA to dopamine {AICHzCH2NHfl. pyridoxai' “0k ’phosphate Serves a; a cofaetor. Given the initial formation of imine (Schiff base) of L-DOPA and pyridoxal, write a chemical mechanism (intermediates and arrow pushing expected) forme fonnationhidopamim mama Il_be Apt“: #9 Ar—Ua Air-CH1 Afcnzuizjt'qty B. (12 pts) A major metabolite of the oxidative metabolism of propranolol is its “lactic acid". Write a detailed chemical mechanism for its formation with formation 0 the ' amine as an intemtediate. R «4.01 6h #9 4"” l: (v W No lat-hm M fl $5 MAO ,h Arocnzcn-CHZNHhCIJH—cag, W RCfllNH-CMQZ ' propranolol CH3 AI = l-naphthyl l . f ,. I - H' Fm' F1 0“: - OH g Q . ‘21:. f (9 . ‘gjq ArOCIizf'ZH-CHzNHz --: ugh/373‘? RC HrNHz 5-1—3 W! fiNHz—fifiwm’? . . . M m ' 01-! "kt." “3* H . amnion—coon ' _ - r Co f meiolol "lactic acid" RC H 9—— R6 [VJ ha I H . Iv - Nhlyglr (A’Jtr He 1"} +3 NADQ “Hz”: IL (40 points) Do any 5 9f 6 parts. Write omit across the pan thai is not to be graded. Compareand contrast the ' expected pharmacolong properties and, where possible. uses expected. ( A. H3C 0 CH(CH3)2 ‘ u ' _ _ ‘H3C—C-O are 9 m Br 9 {gm-3):; and NH: ‘00 —?H‘Cf{2N(CH2 c.3333 m. (40 points) A. (16 points) Given me ' 0 I 0H 0 b. ' | flowing compounds: (CHJhHCNHCHz$%;©-OCH2€H2$C33 CH3~NH-CH2~(':H—Q—o—3—C(CH3)3 H . 0 o‘fi-C(CH3)3 l. l. (pomts) at O pmologicax activity would be expected for each? Give one important thempeutic use for each. 2. ( pomts) Draw partial shown-es of the hydrolysis producm of each. Explain why hydrolysis is ,imponant to the biological Joperties of each - 10 word maximum B. (12 points) Given the - N-CEN N_CH3 ' n following compounds: H3C Cst—CHZCHTNH..C_NH_CH3 Hac CH2_S_CHZCH2_NH_E:_NHCH3 NVNH ' livid: H i. (4 points) hat IS the _' expected receptor target and )4 W 14;. ‘W whalmightthesugcntsbc W used for - 10 word maximum . (4 points) we the strucmmofeachdtlel. _ _ Cub «I‘m-f guufiwl - .5 . (_4 points) hat _ a) ' "ifierences in biological _ j fiver-N y Hath-'in would be expected H:L Mag-“M ' a” Midi/- and why? . C. (12 points) Given the followin co ds' 9 I I 9' ('3' Bra z W (CH3)3N O—C-N(CH3)2 and (CH3)3-N -CH2CH2-S-F;—OCH2CH3 U OCHzcng expected enzymatic target . :mam— differences in duralion of action might be expected and why? Use partial structures to explain. ...
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This note was uploaded on 01/31/2010 for the course MEDCH 563 taught by Professor Wendell during the Spring '10 term at University of Washington.

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MedChem403 Exam1 2000 - F Hour Examination L 'gls 0‘ ' II...

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