problem_set_5_key - MedChem 563P Conference Sections Winter...

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Unformatted text preview: MedChem 563P Conference Sections: Winter Quarter 2009 Tu 10:30—11:20 T473 Th 9:30—10:20 T625 Problem Set # 5 1. a) ldentify the following compounds as well as their mechanism of action QC [-13%th {more go (BB a be, 'éjt‘me, “‘ “ I we. I; wiéifi“ i.» v " -' j; b) What structural element of one compound above is conSIdered a carboxylic aCId bioisostere? Rationalize the acidity of this moiety by drawing resonance structures. How does this structural element contribute to the duration of action? MedChem 563P Conference Sections: Winter Quarter 2009 Tu 10:30—11:20 T473 Th 9:30-10:20 T625 Problem Set # 5 2. a) Why is levodopa (L—DOPA) given instead of dopamine to treat Parkinsonism? b) Why is carbidopa (shown below) often administered in conjunction with L—DOPA in the treatment of Parkinsonism? Show mechanistically how carbidopa inhibits its protein target. k ,. 4 HO ‘ (3ng Ht; ’ CHBWCSTWCOOH NH~N H3 ‘1 3%; '3‘” 4 - 4 w » . a _- at _ 5‘ng (like: 4&4 Biflifififié‘a» l flak waffi 4%» Lsrwfnsgéflfigtww MedChem 563P Conference Sections: Winter Quarter 2009 _ Tu 10:30—11:20 T473 Th 9:30-10:20 T625 Problem Set # 5 3. Draw a chemical mechanism that illustrates the inhibition of MAO—B by Selegiline via adduction to the protein cofactor. Sale-gimme (IfDeprenyl') [Eldepwfl Gotta—cit“ , [EN—CH;— :taCH .‘ 3 (m H 3% J'Réngds 1:3; : - ‘v * ‘ WW MM» E ”6‘ {A} I“ l ex“ ex; 3%.“; w? . = W wsihfiw *7 ‘= M f t t m, «.5351» w»?- wWi‘fiw‘“ ‘ “:3 a} ‘ . 3? w x Kg‘fwfiw ‘” ¥ ‘ ‘ fi , fl 1.. TENA ,r, “3%; “3W £3“ "9 f 3 g; “Eek/Avg” vfigfiwsg“: mmaaifg;w : a _. . . . i . $5 » ‘ waffiw. 4. identify the followmg hallucmogenic drugs. Do any have therapeutic relevance? ‘3‘ (WW A.» the: “ V 5» ‘ X {Whj}; afizfia M7- ~ . A“; 3 k "8%: “E t m5; fig “*3”?ch ms may: s 5? £513:wa mswifir‘r‘fQ We 133‘ 53 IN an i 1 w 1 5 ~ . a w, c , a , M lg » $1233 fiywcwfifi ‘3ng £52 xkfitfi “4,, gwww gm Efgé‘“ flgk ,_ tart. 335.0 f’hf’; ”£0 a wt, (4.11m MedChem 563P Conference Sections: Winter Quarter 2009 Tu 10:30—11:20 T473 E Th 9:30-10:20 T625 ‘ Problem Set # 5 _ fi fie WM Sf {:32 5. a) Describe the blood brain barrier (BBB) as it relates to CNS drugs. What anatomical characteristics define this tissue? What important physico-chemical properties must a majority of CNS agents possess to access the CNS through the BBB? A MAL vs!“ if ix \ b) Describe a few ABC efflux protein subclasses including any substrate specificity differences 3&szme . { em» W at between the various types. . 3%? . “a. S W a we)» ; SW53»? x m 6. Explain how Bodbr’s the CNS. My”! ”my X |\ ”w MedChem 563P Conference Sections: Winter Quarter 2009 Tu 10:30-11:20 T473 Th 9:30—10:20 T625 Problem Set # 5 7. Draw the core structure of both phenothiazines and thioxanthenes and describe the five main structural requirements for antipsychotic activity. ”i N M cg R mad: we a 2 MedChem 563P Conference Sections: Winter Quarter 2009 Tu 10:30-11:20 T473 Th 9:30—10:20 T625 Problem Set # 5 9. What are the seven classes of antipsychotics? List the prototype drug for each class. E 1. e, :x " § 1 , ,& team‘- a) “13‘le f», 10. What are the four main classes of anti—depressants? What are their mechanisms of , WM“. MJ [M _.. t g 5:5“ Mr a" «at r a. gm ‘5 ; ‘59s“ .Nr‘ t ...
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