Medchem563_Exam1_2003 - 1"“- Medlciml Chernisrry 403...

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Unformatted text preview: 1"“- Medlciml Chernisrry 403 Write neatly. Confinc your answers to the space provided. Lfl (16) Hour Examination 11 W“) (38) February 5. 2003 111 M (25) N-__1"1\'___. (22) TOTAL____ (101) (g6 points) Given the following two sets of pairs of compounds where a very im portant strucmral differ-coco is the mhstitulion on a nitrogen atom, indicate what pharmacological activity would be expected for each, and indicate why ph yaioochcmicalcfi‘cctsmodatcdwfithflmniflogenatommimpommmthc . difiexenocsinpossiblcthuapeuficusesofflacmembcrsofcacbpair. i‘rr'c”. (1) o ' . (CH 3 Bra H4 “((311332 “3 ‘5 CH3 . and H3 ' m3 ‘9 “A wwwmfl‘h au- MHE inhibitors. .30 ‘ ' m 41‘ flunk Salk) , buth I ‘ ‘ M 09“"8 a“ M“ '3‘“ ( . 1 4-t.cnto\._ U oi?“ W: C N; amtqovr. -\MEVAT3£WLJLM “HA {deh- r: _ a . , 1., Ww_..tt_ High 1 'uA 42.41%.“ mm» ,Lircw in fenL'rmi’c 41., $33. an [a 41;; \MA K i “' by. mack ADM Argon/rm. . x 1.” it atbln‘ouickg . o ‘l a,“ n‘L\UC{’L"\. ‘~ ‘0‘ go I 'V Mu} «Br (1‘ MM {JACU’gt Lu MEHBQLV‘ (9%“) 4411} I {mum (pun be Pcptic LULut. ‘ iulxaidiou 'wx Mdfawm . .kfib ludvcd’e ’“ru BBB, LLlccl ' a new vwav. Jul f 110 P - L2} 4) LwrdAocvcac , fi k wtc‘r 1' Du fit"- ‘A‘ S; - H“! M (‘63.; D \n II. (38 points) Compare and contrast the expected utic uses pharmacological properties and. where possible. the expected for members of each pair. Explain why these differences are expected to occur. Include what leoeptor or other biological target is important to each. Write in complete sentences confined to the space provided. A. c 3 cnzcazmz -C':'-".N c 3 CHZSCHZCHg-NH -NH-CH3 :3 N: — and HNVN H V 14 M MW‘Wz—Wm “mst “a W'— Wmi‘fiigw E‘szw.w 0H " and O OH H I 1113(20—c—ct+Izcnz-C‘>-00:1ch—CHZNHCH(<:H;)2 ocnzéH—CHZNHcmCIhh Q Mwfi"WMWW “'5 m and CH3 CH3 0 ' I H2 H3813'CH2'CH2'0' 'CH2‘CH2’E'OCH2‘CHfif‘CI-I3 9 CH3 2131-9 CH3 2. (6) Write a chemical mechanism for the formation of an expected major metabolite of either of the above compounds. MW 1% {afimgfimgéW/gr hi) I‘D ; +- 8 MWMQ ‘% first-- A W H a 0* " W U? by; K” 3 than III. (2.5 points) Limit your answer to the space provided. Write in complete sentences. A. (10 points) 1. What are leukotrienes and why are L'I‘IZh-L'I'B4 receptor antagonists are potentially useful drugs. Luke-{4x146 w- Float-id“; £41.; §-!.-,.,¢Q¢M,¢ MW, «.4 are “d:‘+"” ’9 WWW-id?“- LTGQ Ins-i L04 antacid-n1 u/ LMckm‘Wfldl'fa" «.1 LTn‘i-LTE.’ (at.ch qdfsfqis‘f‘) Wu 1,‘ owl it"me «1%.... - 2. Briefly explain how muscarinic and nicotinic receptors differ structurally and functionally. indicate why this function is a potentially useful target for development of inhibitors. 1. tyrosine hydroxylase Hlefich“H£ (L8 ‘- +Yflgv£ +0 A:LtJrOXYlfl¢uY’AIKW;-4( :1“; IS “ac Vfih-limifi'n}, 3" “E _ 4M1“ L :‘h‘lm w r hf- , “"1 Glynn-«inc 19:957-1fo“5‘ ;-q 4/ a «1+1!st e‘fi #‘flt Y . oL-ad-ILvl—L-‘i-Yrou-IC r... a tying-M ngfogvl‘w Mklrhr' '+yxos.'nc3 1L n4 exnmf/f Wu“ “C Lem-NM» at M. t... “‘4 flak-,1 '- C494 . IALILl‘frofl Jame M” “lam-K 45L syringe 3. catechol—O—methyl mfezase Cari-“113:5 4x: omfiPLYI-t'l'ib’t 0"" i‘LC Ck+¢oLaLvti4C .' Inkln'hd etc COMT me L: fliers/udzsflfi MM M Hid; fink? chu Platte}, TLC ‘5 W JP Jere-L7“ l; Fulfil” f-{u (4- sf? Ctr-J L¢ ' 7 k M AI] an s... .3 1x4?“ _1n~c+.‘vfil"n‘°4~ Nth-lath all as“ MT «mu k Jamaal. Mn. ‘1 N “J, TLEj':I-‘l'-'C {CH/’1'de WC liafi'd—éhfvgfl fd.‘ ck‘anlj “Jr 4/, a# “°“""":i'i:;°? "‘ “M” (*nfiJfi-mg‘“ J‘s»! Mum! 1. A: 3th.», :- Lutnfi" Ufa-fl Landfill}, 6F 2'- e-MJ" 0“ Coqgrflq-fl'ofl‘l .t if... M "”**c°r"““§' +12 earn. 1,, # nerd new:an an, 67"“;4‘ ward “din—oz; (in-«NS "a" g 7 W‘MML “(A 1:“ =:n,1-t TLC $045+ {walk Ell-raullul-ILI «kw-hwy sew-Idem, «(near/ 3712a; e 5‘ 7 $31,113. (15 points). Indicate the physiological role of each of the following enzymes. Wherepossible. “WKHHJfi I. (22 points) A. l. (9 points) Write a chemical mechanism for enzymatic communion (metabolic) of histamine to the :3 corresponding carboxyiic acid metabolite. was“ CH CH NH 00H _ 2 2 2 _} 2C 5 pit-{>5 H , histamine H Ea H- it ' ' I Eqklgfi lit ,3 Fl Vn a, afihfifi Mt) “50 and pfl-F H FIH‘ PH?" “2) -3" . H g9. 45-”...flk44—J- E‘CHS—‘—L:J'+z_ TE; E-CI-i-Gro April-14 H “1+ 7_ K Clair: 2. (4 points) Draw the structure of each of these two compounds at physiological pH. pH 7.4. ,ath ,ruhw‘ae no to, M‘%,& g, 45237351.,»51214 (#9. 6*?) a-! ~ ' A B. (9 points) jaunt phosphate serves as a cofactor in the manic decarboxylation of L-DOPA to dopamine. wen the initial imine, write a chemical mechanism, with intermediates and arrow for fon‘nation of dopamine. W HO 5 "0 V cog. MW Ho,©_fl2\$ ME: 1%“ 9.0%”; 0 Rainy "’ ncfgo art \ { ._._\ ' :b—Ee A 11m, fl .5 I L-DOPA Hg P \ ' H 1' Ho 15 ...
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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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Medchem563_Exam1_2003 - 1"“- Medlciml Chernisrry 403...

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