Medchem563_Exam1_2002 - Medicinal Chemistry 403 I(16 12...

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Unformatted text preview: Medicinal Chemistry 403 I. (16) 12. Hour Examination 1]. (32) February 6. 2002 III. (20) Iv. (32) Write neatly. Confine your answers to the space provided. TOTAL_______,__ (100) I. (16 points) A. (8 points) Pyridoxal phosphate serves as a cofactor in the enzymatic decarboxylatiOn of histidine to histamine. Given the initial imine, write a chemical mechanism, with intemiediates and arrow pushing for formation of histamine. Ar Hf Hz...h “83 "E": Ar'fl’fi Ar-crt; HF”— C i w .. f": ll \I/N ‘50 M ’Lfi =5H, Half” C H I ""9 an -—-> Gran e “I a If a .H M - or or Lew ‘ L: t. c”: 0' 9"} a ' 6", R a H H 1% ” J! .... Armani“. CH ,NH 6 RCHZ 2 ' F+ r” “’“M + o .4 H K I ~31" ain’t-J Fulfill) "h alt/1‘ R : H finder! of, t”: 8,01." :4 B. (8 points) Write a chemical mechanism for monoamine oxidase catalyzed conversion of norepinephrine to the coxresponding aldehyde. H, OH H,, OH HO " HO DAflgNflz —)v W H H0 H0 63 1V on F! ' F! ' n \7 He + —, cl! 9H1 Li; R art—UH ———=> R-CH- H3. "’ ' 1 L’ 3/ II. (32 points) Do any 4 of 5 parts. Write omit across the part that is not to be graded. Compare and contrast the expected phannecological properties and, where possible, the therapeutic uses expected. Explain why ' '2} ,2 1. these differences are expected to occur. Write in complete sentences confined to the space provided. at. a H /C 3 (I) and egg (I? on, ‘Cfiz-CHz-d-Offlz-CH H2 H3C-I‘II-CH2-CI-Iz- ocnz-CHz-o-c-CHZ-mzqf-cna a??? 213:9 CH3 (0::- HM2O and QéH-CHZ—NH-leish 69 Q H0 - gfimh' “v (1644.» _ :fi’fifg/é“ ‘42:" I h M mwgmiw” Jim) W“ “c” ‘ 3'“ ‘ J 2’ a ;%fi;.,. 5%” #3 222149244— gawg 1y” ' M M 5"”; “1'1 eff“: ,— ) [z 734'" ' E. rm" H“ W c 3 CHZCHZNHZ erg; CH23CI-12CH2-NH —NH-CH3 ¢ ;——< and _. t 111. (20 points) Limit your ans to the space provided. Write in temp! sentences / W A. (8 points) Explain what leukou'iencs are and why L'I'DfL'I'E‘ receptor antagonism are potentially useful drugs. LeuJLcI-fienes m mMast M 9m AmaAfeénz‘c ado! A, 5—{ipok1fimaw MA GuW‘F glue-IL“th cmjuyd-p‘w‘, m, m hrs-Hm.» :ncA}an5 Adam! L, «HQ/antral mad-621%. 0'12in WM W-FSJLI» m We»; old/gs Muse. Had:— ‘Hw MRFLVIQ°£t "SPWSL CMoemSJr-kfi‘n) VaSqua-f pwmle-D (Ludo allergens. M 41099 my; 5L I a. [ PM“ 4;, ‘I'gu, W “sf-“MA” Iv. (32 pomts) A. Hj—s—cnzcnfimmh Bra Ill-‘5. 'I . y. i: "Ff B. (12 points) For any 2 of the following 3 enzymes indicate what its physiological role is. Where possible. indicate why this function is a potentially useftfl target for development of inhibitors. 1. tyrosine hydoxylasc Tam-Sine WW ‘H-q, mma ac:‘f fimsmt t m: rs 4h Me hwv‘w 91?? 9n 1% “films 4? Jyw’m, .. ‘m, Moi alarm/2 mm. Ink. rim ck m-lwiiyl rug-ma who nae—Q»! (L;- vawme Wb‘FVMWFflfi Wily 2. S-Iipoxygcnase downs ‘R‘L Emma“ 09 MAOLifiL/V'II‘C. it; fnw-dt epoxloL. ‘mLDJVI‘U‘L. fiq. nil-6.5, defuse. ‘i‘f-L synMeC-is 543 [atoms Mel W W 1%. efi-‘zd‘s O‘FMRM/Dfihyialgb m. and 1:“- bnmci'hiof M9i1'EC‘h‘m. 3. aoctylcholine esterase ~_. mialvm +£4- 5175 5'0 Mé/CL/Mb, W‘UmMoflll'Hfi #5 Min}: 4": A new—a Mfflizéfli’. a? (M9; M MW in Hewett-{ML #flftegaaffixs, W; up as“ A 9"" Alumna: efi C My“ I f mafiwm Nimitwb 2‘" 5 K a V m - (12 points) Explain how the following agents produce muscarinic effects differently. I. (6 points) 3 3 ‘9 e HQN H'CH2N(CI:I3)3 Br i. :‘.-’"."-'.l. _ In paints wen e 1-— following compounds: [-1 OH 32’ ,3 H; ‘CH, ‘cmcuay2 H 2 HfiHfi-OM: l. - mts ve e structure theexpected f /° - ,2, major metabolite of each. '3‘ ' 0 . pomts pam "ramléu, . what pham‘mcological 'fl’ ‘_ activity would be expected a M A W of each and from the w expected major metabolite _ - ° of each‘ _ ' W“; ,. MW 3. . pomts) Writea chemical mechanism forthe 0% 5’9 . . 0 1 1' fl}, fonnauon ofthemajor 0.x _ _... #4.], debfl- 2L metabolitefmmgngof “0/ JK (fl-70 M K 5” I0# 3’ (+70. ' 5% I!" I p l_gfflft £fl~§aofi 1‘ [1450+ flea-1W”: "##9- fl 1C 55 - 25% U ...
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Medchem563_Exam1_2002 - Medicinal Chemistry 403 I(16 12...

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