MedChem403 Exam1 1998 - rite neatly IConfine your ansWers...

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Unformatted text preview: rite neatly. IConfine your ansWers to the space provided. (20 points) Explain. Write complete sentences limited to space provided. - l. The rate of hydrolysis of acetylcholinc (ACh) and ethyl acetate by some preparations of acetylcholine esterase in vitro is approximately the same. ' _ . O ”W” ‘WHY‘S 5"“? 7"“ W39” '5 mmmi CH3-E-'OCH2CH2fi_Me3 (ACh)__ 44%. We regatta-<94: “‘2’ “Wm" Saw ”5“!" -' 9 .fi ' . . _ . _ - CH3-C‘OCH2CH3 as equivaievul' esi‘cw mfll‘ofi‘a 50 fit; overall! {who will be ' 4cm Rw- balk svlo's‘lrau‘es. ' 2. Inhibitors of acetylcholinesterase are potentially useful in the treatment of Alzheimer’s disease. (senile dementia, Alzheimer‘s type). fiiéhamers is marked b3 “Wease- 5‘4 Sarawak awluoks’h‘ae in areas 0-? fine bralih- If fab! Cfidfimn be racemedél in fine fi/TW55 b‘fi W545 'flChE') +45% ai-me‘fomsa‘il 1%ch can b2. dim M'i‘sheoi' ' . - - . 3. Inhibitors of acetylcholinesterase (like physostigmine) produce different effects when used to overcome the skeletal muscle relaxant effects of pancuronium and of succinylcholine.‘ ' _ - - . _ . OAS CH3 I [awareness is ¢flpeishm mdxfio‘arn—Da NM‘S Me‘ ‘ 1L1“ blodfl-W'. I'l's G‘m'ccz'b Cm beavercom pr WMW‘W' N I '- b‘d imaged, Citron] “whbk is accomplished. i=3 19% E O Inhibit?“ ‘55 Fhfisofiligmmeq Sire/infaldfidine'. i) 1401/: MMifi I 9 _ + MOL Molar Fling Q m film 3', It: M ‘ Wadi be '(CHzCOCI-IzCHzNMeah 4. . Phosphate esters like malathion is useful in humans and are WW. 4514;1de [elm/load Matti. mama med-s +e' h: melee: “lo . i. 900% Wanna 46 be as (den-Pas scrim.- r39”: M5905 “ML .m" memo-n-smcnzcoom ”aim“- LW M “w “419. WW3", man Has bigger dams: adim'lg 3013- Miami-on MW M¢~M6frbre will clau- bmc’i-ghzlifig 09' “34% "gerbil—F sarin .. x 44mm oxide-Hanna 1mm hm low (9+ch “om-hi “M ocmcflm dare/Rare, Crete-he MM“: 0‘: We“ irreversible‘ipxoyki! C'mvfuicvlil-er . ' ‘ ' . ' - - - it . '1 WM '5 #1: WIT-LC "4‘ 6615+). Miriam: firm, hi“ hi? Wadi, hgobm'igaalole “"f'f‘lm‘wl‘ .. ‘9 5:” mama (arm. E « ‘ -%_'Sarivt fs-afafewl’ mr‘ym” “Md ‘ pancuroniun‘. (40 points) Do any 5 of 6 parts. Write omit across the part you do not want graded._ Compare and contrast the expected phannacological properties (and possible therapeutic use. if expected) of are following pairs of cogpounds. Confine your answer to 35~50 wards in pomplete sentenm using the space provided. HOQCH~CH2NHCH(CH3)2 __ and '. _ Cl Geog CHZNHCH(CH3)2 . - H02; 1; ' rfiMM‘ Wfimflfl 9 '1 ’« fm,mW)M‘t“fi“W3“ "~ )aerada— . , - M of .——. - mlgwwg‘Qg‘éwufiugthg/gfihg .“J WWI‘Q' 2- W' ' H' N-Ca‘N- _ I _ II ‘ ‘CHéSfl-IzCHZ—N-C NHCH3 CH CH NH. HC. _— CH3»? 2. 2‘ 2 and 2"va . a. g NWNHWAM 41W Lo a M; M . _. _ ‘ _ I _ ‘4' .'E ’I . _ - .' I 0 - \‘\ . . . . -. 3. ‘HO. H CH3 . . ~.. _ . R . _. . and ' H0 2 J CI'IZ N H$HCH3. . (‘06; Swan? 1 CH3 4 ' . j - HO ‘ ' 3 - . A . ‘cnzcnzocag, I TFW>M5MSL 11.5% .rm‘ph g 5...: Av ‘— A . 3 \fi/ ( :02 _ . Hacxlskcmcflflz . I I . .0 _ ' I' .9 . . 5 Ff” ,1_ 9’1 2%) 1%: A. A ‘ ‘ 0 ~ 5- ‘ c4; MLLj/‘flimw [gap/k614i, . 3 / -. *2. " OH 4' .CH—CH2“NI:I2 . CH3 ’4' . . .. ‘. WJM a» ‘ *- b F 74 .‘ Z W? ' ' 12 A, way. WWW-(41% 6MWMW’ . In points) . ' ' (2013;.(8 points) Show by writing a chemical mechanism (including structures and intemtediates) of l m 2. 1. How propranolol ts metabolized to its "lactic acid” metabolite. or Fl f 2. How histadine ls cgwerte to histamine. I! L, Fl H _' ' OH A . a _ _ Yawn-«r d’sfifl *fiztr'fflh _-—-r RVs/13‘“ ‘ 7 W ' moanzéH-mcmcngz ' ' ' A11: mm _ ArOCHz-CH-COOH _ gal-l dc F'JL—Jfiu ' I _ Ar: l-naphthyl h e,— ‘ v t.“ . + it . . IflHa . O hn-CHz-cwooo - histadine ' ‘ u _ ' u - ' . f x. mg- r‘\f_a .Im CH2CH2NH2 _ hlstan'unc /"'w g ' R m _ . Rig; . 1 = N VNH . \ :3. -—e- u! ' . - _ ,1”. f < d" . I ' - _ ‘ . ' 31 gr _ 4“ B. (112 points) ' ' »0 MA" ”’ ’ .(4 pts) These- two prodmgs“ have been used Based on their structures, how do you think each wouldfcould be used and why? (CHahN’O 2. (2 pts) Which would be hydrolyzed more rapidly and why? 1, m4- ‘vMQfi-BMNM W4. . CH3)3C- c- O’CHCHZNHCH3 ( p, xii-”cm a z: nwmxfi ”M‘- .me - 14M - z“ W a ' ' -W ‘ __ flip/.74, Hm'zerofi M 32“ - . / 4‘ 3 (6 pts) Write a chemical mechanism for 31¢: conversion of one of these to an active agent. 0 ‘ Hm: cgfl ‘- H Hug-C“ gc'flHIA-P- - -"'7 M(SC*9C +A'V'04tI mmmmwmwwwmfimrhmpowbaMm b 'S-adenosylmetlfioninc An” 0;: 44a:- _-H1ne.,_ . ' 14M 315 a. co—QmL-l-Wfiar ; ..., can-Riding “wrest-“Mg rwpm'nd ‘93. Phanglr Whammy -U-— anu +msfismo in canvwfinj 5; 4195-91. (Ir-TM ‘m 2‘?! Sjn'k'W-‘I‘SB ; , . - . ._ —-;I+'-i$ also team! in haHlalen 'H’u-r ch-f— "'9” 53an ”FF c‘j‘k‘fhptfiim; Lruoi-imon‘l'dlgm [as (La . T705 9 Imrrr-Fmrf—Ih-Mmm-Lfinj +A4. «ac-41‘0” OF' Cari-och blaming; . ' #8 'I “SI-d .‘ 4H,“, mahfaonikm 0F fifS‘f‘QM-c'hfir In whit/‘4 14-5. M? of M3 . ‘iswmlefl'flj [AA—VA? This (Mdtrg. hrls-Fmim mad'lva, I’ll-(min: in-gcfmmdfig Was; 2. sucralfate [sulfatcd snicrose-l-AKOHh] . . _ ‘ \ Than non-absn’buf GMIW .Ioa-rbplng M is LIE-LA 4171/ - ‘H’W +rm+m4f pf— Furl-rs:- Delmar. I4-awycs. RE- A- Fro-Fcoh'v-L. MAJ-fag] 9.; 4m PMs mi- 44”.. MAC-4f we, aomvw'wg -‘H~b dfdufivc, (aw-Hm 0-4 Pupsin and add: ' Ar heparin ‘ . . _ - - . . 3:4" 1':- . an Mdt-Ll SIWI‘Fob‘i—Ld g; SWHO which [email protected]"m-'=j- 0; (WMFW =WI'HfI his-kamfru— via... _. 4. leukotricneC4/D4 . LTC'Iq- and 33—91.} m "40'!“th :1ch MA 'FWM le‘danl'cv _J&I'd 193‘ E‘llflvaflamaE-e and! 5:] S‘wbgwgiwfvjfim: Wijm‘hm r‘ Bra-141 an... _modl’t\.-I'urs (7F b’bndum-l-nuh and VASower' ”mm-H (:thlw+t rem u—PM inWHo-fl . WH’A nffmffixl-o W\.. — — ,A \‘ J' 5 . | l ...
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