{[ promptMessage ]}

Bookmark it

{[ promptMessage ]}

Medchem563_Exam2_2003 - Medicinal Chemistry 403 I_V\lfl(23...

Info icon This preview shows pages 1–6. Sign up to view the full content.

View Full Document Right Arrow Icon
Image of page 1

Info icon This preview has intentionally blurred sections. Sign up to view the full version.

View Full Document Right Arrow Icon
Image of page 2
Image of page 3

Info icon This preview has intentionally blurred sections. Sign up to view the full version.

View Full Document Right Arrow Icon
Image of page 4
Image of page 5

Info icon This preview has intentionally blurred sections. Sign up to view the full version.

View Full Document Right Arrow Icon
Image of page 6
This is the end of the preview. Sign up to access the rest of the document.

Unformatted text preview: Medicinal Chemistry 403 _ I._V_\lfl__ (23) HomExamination - II. ;T P (13) March 5, 2003 JILL (28) NASfl— (26) Write neatly. Confi'ne your-answers to the Space provided. A. (10 points) W. The following two agents are important drugs which apparently have chemical mechanisms of actions that involve covalent binding to important biological targets. For each, explain what it is used for therapeutically, what is the biOIQgiCfl @136} 0f 83011, mechanistically how it produces the desired response, and why apparently each 18 speCific in its action, 1.e. apparently has a single biological target. I omeprazole @ VMQA‘f‘L W3 thMM. H30 CH3 ‘5 " calla t‘a—ffl ~ H1 M . M {MW WW%(MW 1:;me . Frau-Dim 2 carbido a #7999“ $3415: “A w ‘ P (EMMA—‘4‘" mm AMA-<9?” £113 9 I, “”va 4W ' s +5 H0 CH2~$J000 "flu. . _ “Mimfpiueg: i 4...- H0 W3 gggfij‘ 2 B . g6 points) Compare and contrast the expected phannacological activities and therapeutic uses of the ollowing agents when admirfistcred systeigqlically. Explain why you would expect significant differences‘h («View H"C ‘CHZCH2N(CH3)2 E .’ 5“”“7‘” ' git-5! w”- MLWWWEME'M ELM fW W210 I fimzizw. ‘11: WM»! ‘1’;ng {4“, www . $th 'nts) The following enzymes are targets for Mt inhibitors thin are noefitl in the tteatment _ farldnsonism. What' is the function of3 each of the enzymes_and explain why inhibitors would be useful' in the treatment of Parldnsonism. psi-m Q'mdfiyw 1. catechol 0-meth ] [£33360 W%%% 57; 5“ M92204 fil‘mmaavw 4%,sz; 5.2%; “cl-”:2: W444 WW _metm H54”- . - L$3P$W 2. monoamine oxidase-B M406 “Wow WWW; WWW we... , - ' Law “ . W at» “7’7”“ mm- Awwc- (4n tic CM: 1.. Wfiw mévflx. W D. (6 points) The foHow' 3 compound' is a metabolite of di enhydramine. Write a process, with intermediates, that accounts fonts formation. @\ pit, #0 at at: .._>- J'fib reg/$9,, thCHOCHZCHZN(CH3)2__9 flip—«1'3 at 4L J—j _ diphenhydmmi ne :2} l 5 Ph CHOCH COOH (J :‘3. i1” ,, 2 2 I + {‘4 / H M fi'o Lou-m u 243‘” led biOChemical Cort 3 (18 points) A wide variety of drugs are marketed for the treatment of unipolar depression. Oftentimes, lack of drug efficacy means that the patient is switched to an alternative antidepressant. In some instances this has necessitated a lengthy washed-out period before the second treatment is started. This is particularly true for tranylcyprorrune and fluoxetine, the structures shown below. H CF3—©~O-CH—CH2-CH2-NH-CH3 NH2 H (“I‘AL c 1 1|. Mwl A, (4 points) Both of these compounds increase CNS levels of biogenic amines. Contrast how they do 1% :«KM :10 this. —-- M - - _Tm1lc1prmnz tnmuu lewlk ml1 1.33th “Int-1!} m J-Le cuS L, IIILJLH'T: (VIA-o. " T""‘7"Y"“““" “ * what». 5 «l mkbmr 04" Miro. E. angchdg FLOX¢+M¢ 5% LIN-J‘s +L". {to fak't d'p SCTU'I'DHCVI (Std-”'5. .Lc . . ' 21$. (8 points) Explain- for each Qflg. why a lengthy wash-out period 18 necessary before in t . switching to a different antidepressant therapy. (Different reason for each drug.) 3:142“);ka Bull'l Namath/rt «ml #5 Aoftvg cactslazl-‘H- norpleowel-me, J. (“Jr kKV‘L txflaijr lwttk J ““11 30 t+ +ak~f$ N 5' qu'fl'll'x'fg I E Sula-rtekJ) 3+9 1‘ +1 ”whfig-at c°“Pl€+¢Ll Moxie. 444:; 53R]: ken, HM, 373+¢M.IP ch sw;+¢h occur; .3.— vf 990“"r +1“. 064:1qu {IN-ed”: 9-9- S‘Hr rcuphktt ”taller-PW" “ml V4190“! ._ 3-H." a s gems» «mete... m emcee . «.LED' + ,. 5 - - ""WI‘TP'WWM D °‘ Mtokmflrm- eel Mad-txrd'or 0 M40. Me??"' ‘5“ -. L MA-o rs .:. - L-L.+,J . ’1’: - T M - - 04h! fro-11: foufl'flfi “(apart a...” tor-M flu Srjfim.‘ tsgrg’fm“ amt «Wat. cm W 52m“... primal.- itdgzam ' Mug. (6 points) Dietary restrictions involving foodstuffs high in tyramine are a problem for patients w o (”9”! being treated with conventional MAOIs. However, there is much less of a concem for patients on the newer MAOIs. selegiline and moclobemide. Why is this? In flMm/e casts fl ‘1)” mt Them ts has all a._c.ov1¢ern when «JM;n;s-f-¢r.’n7 39-153" Mt {a In. EL Elfin.“ o‘uL +9 S9l¢}£l€‘4€. tact-x), 4L :g’ec‘lv‘lfl ("1&2_£ {nLlLJ'N’i fi'f' sfiflgi TY’W'F‘M- H perv-«MM MmLal.-ed b7 Mir) #4- . M SQk‘H‘R' arc, is. his a": 0L. concé‘m INLM “J“:"ts‘r‘erJ-A}, MUL’OL'MUJ'L Eff molalmll slut +0 :+ bu"; h 5L°‘”+‘““= reverszlle M40 :«LIL‘WZ RIM")f TIM older M o mk;L.-+Wt we ;¢rg¢¢n.;u'€ rn’leV-u‘l‘?“ + e mew-e, leggy", 11: t‘tant'ctcad‘l' magic—“M:WQ ale-f. +0 log: .94: W‘s. ‘Ftv'sl- Eat; mc+a1wflifi. W/ fifiul-lrffJSt-flL :st IL dwarf. _ /--—-_._ IH. (28 points) B. (15 points (3 points each» Very small structural changes can have a dramatic impact on pharmacological activity, as exemplified by the two tricyclic drugs (A) and (B) shown below. Contrast the following: 0‘. Cl ’C"\ ’CN H (CH2)2-N(CH3)2 H (CH2)2'—N(CH3)2 A B l.t cir erapeutic use 3. their therapeutic indices - . imensional shape metabolic N-dealkylation A. (13 points) 1. (3 points) What centrally acting agent is this chemical delivery system (CD8) to the brain attempting to deliver? T 2. (8 points) How does this type of CD8 work? Explain fully. I) Um; alkyd/IRWMM «samba/axles Cmsscs $35 paégwdy. 3. (2 points) What additional modification would you suggest to reduce enzymatic breakdown before it reaches the CNS? Hat; m-l’er mmeQ. Mvafiw'xo Helm. Aid-cf" kyol/SESN M 14‘... M‘fimouvemiot IV. (26 points) C10: and prazepam both exert eir pharmacological effects fo common biologic y active product (X). I: on V K . o Cl - COZK I ‘0 o a 0 —N A. (Zpoints) Nach chlia3epdm B. (4Ipoinls) Araboth [email protected]? Exilain. " - . n-lr: : ClOTab-‘PAIL I'o 4+;T‘god‘rug 414: It 61016" t “a“ “mi ‘ "5 ‘- " ft '6 ach{b\| M1 4b.]; 4M1; H's aghgn only LON—Rh I (GWUUIIJ- +0 noral-‘nypam in‘w‘vo- On hm omv hand 1“,“me dd”) h achvibwand Nnu it 65 not 41;;le a p'rocJ-r‘ufl- (RV-t 501-714 I'rfl'n'hsi'c 6 C. (12 points) Draw an arrow-pushing mechanism for the conversion of clorazepate to X. Include all the cate w c .P intermediate ste . Be sure to show how gastric acid partici tes in the process and indi step :5 irreversréie. H OH $ I K (’4 $ . _/ \ \M‘V‘ Ff,— H' H n a 0-4 0 ._ “Lo flex/ 0 4--~ OH H H ——-v H H a " 0*“ Hoihrorn N Coal-1 5 N 3 Jazz-:- "' 3" Ira-04 U A l “a” \‘K 1': 0 ”I; E: or! /r‘\‘ H- / N V - kahuna! / \‘( 1.-——-- I H L—_— , 1 also ,. Mubfiufi‘“ M/ J‘ 2' ,- tv {T if; H .— q :1" OH "' N chI-aMPflm- Q 3 D. (8 points) In humans, oxidative metabolism of X results in the formation of an active metabolite (Z), which now has a chiral center. 2 is marketed, in its own right, as an anxiolytic, and is available as the racemic dru . Draw the structure of Z and explain, diagramatically. why there is no reason to even consider mar ting either of the enantiomers of Z. ‘1 Le o We ‘9 2 E03 “ on -—-———'P U- FI-tv‘so (,t Now (1 iagz. pram L23 ...
View Full Document

{[ snackBarMessage ]}

What students are saying

  • Left Quote Icon

    As a current student on this bumpy collegiate pathway, I stumbled upon Course Hero, where I can find study resources for nearly all my courses, get online help from tutors 24/7, and even share my old projects, papers, and lecture notes with other students.

    Student Picture

    Kiran Temple University Fox School of Business ‘17, Course Hero Intern

  • Left Quote Icon

    I cannot even describe how much Course Hero helped me this summer. It’s truly become something I can always rely on and help me. In the end, I was not only able to survive summer classes, but I was able to thrive thanks to Course Hero.

    Student Picture

    Dana University of Pennsylvania ‘17, Course Hero Intern

  • Left Quote Icon

    The ability to access any university’s resources through Course Hero proved invaluable in my case. I was behind on Tulane coursework and actually used UCLA’s materials to help me move forward and get everything together on time.

    Student Picture

    Jill Tulane University ‘16, Course Hero Intern