Med Chem Exam 1_1999

Med Chem Exam 1_1999 - l" l a a pure drug from...

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Unformatted text preview: l"? l? a a pure drug from plants. {were Friar“) if? ,- ." 1 Name Medicinal Chemistry 311 .. . Student No. October 5. 1999 Examination #1 Use your B-digit person numberI leave the last 19th! space blang. For the multiple choice questions. Elect the one best answer. (2.5 points each} If you change an answer. be certain to erase the original bubble completely. 1. Medicinal chemists a] discoyer. design Eisynthes'tze drUgs. ‘5' crqdrlit” iii/tt’i‘rilf-i toil Wanting. b) design 3: make drug dosage forms. e.g. tablets. r' “- LLC emamj c} are inorganic chemists by training. id“in g .-i a d} primarily study the effects of drugs in the body. e} a at c J' n. Lil. Lt £1.11 a. IEIL For questions 2 8c 3. select the appropriate person and enter the appropriate fr $513 ri— letter on the bubble sheet: a) Friedrich Wchler. b} Friedrich Sertumer. c} John Abel. d} Paul Ehrlich. e} William Withering “"4 a. my.” I .c (J Le W U"- ‘it 4* l 1‘" tiEa'TEii.1|i5.l-i cttirliiit their: r-irr‘*-.! : Neel-e as. L. ,ore-rt 2. The German pharmacist who was the first person to publish on the isolation of “W Metric. a met at 3. His statement of the principles of chemotherapy included the ideas that '1 i“ ’35 chemotherapeutic drugs would haye relatively low molecular weights {compared to proteins} and would act directly on parasites. Fain Eta.» helm 4. In the U.S. resistance to chemotherapeutic drugs is especially a problem when treating infections caused by Eyelet tat til it; tr: t iii. a} molds. {l | ilirruli ‘i'i. i'i’i’dt hiiungi' —| “triftl Ci l'iilflfi’rli"t;,-t . C c) bacteria. L'L ' ' ' ' _ d} protozoans. e.g. malarial parasites. e} a 3: c 5. Examples of classes of drugs that are made by plants are _ Lw tl Envy ya Jill a will ” -. ii“ a} alkaloids. e.g. codeine. OH 5_ 't'ilnl‘ikryt iii-pit: f b} purines. e.g. theophylline and caffeine. .rtll? be” tilt” 1:; c} cardiac giycosides {steroidal sugars}. e.g. digoxin "r e} e s c. e} a. b. 8: c. 5. Compared to the solubility of alkaloids in water. the solubility of alkaloid salts such as alkaloid nitrates. sulfates. and hydrochlorides is a) less b) greater c} not affected because alkaloids do not form salts with acids T. A structural feature of alkaloids is the a} alcohol {-DH) group. a“? hJ-LL b} carboxylic acid {-CDDH) group. . at" (O c} ester r-cooe} group. d} amide [-CDNHr} group. e} amine [-N=} group. 8. Drugs from natural sources such as plants mayr be discovered through a} screening programs. b] toxicity.I reports- r c) ethnophannacologyffolklore. L-- d} b 3: c e} a. b 3! c 9. Drugs obtainable from mammalsfanimais include I a} penicillin. _ . “flip? ' blestrogens. fiflflflldfi “33 Jig-We c) insulin-1 H” C d} b 3‘ '3 l“"I'icphob‘ it e} a. b 8: c ham-rang lb. The following structure is EH3 UH r. E b it u ‘I' ? {all ' .'r~£. J I If Eli-"j HO i an”? a} an alkaloid b) apolvpeptide i) _ - I ,. . I; '1t'1flL-‘F; -» _ . -. . , C Ella Star?” "* ' tLLJIEiarerttanrj[itv‘l'ujgb'rm-l'urtt’ttt‘rlfrflrtWe a purine ' ' e) none of the above 11. Engaged in a program to discover new drugs from plants, you identified, collected and prepared extracts of the plants. Your next step would be to purify the potential drugs contained in the extracts and characterize them usingr e.g.. ultraviolet, infrared and visible spectroscopy, nuclear magnetic resonance spectrometrv, x-l‘ay crystallographv. a} TRUE s} FALSE 12. An example of an antibiotic {obtained from nature. by definition) is 'agcurea _ I II {if _ bitetracvcline choir Farr-“int inst-H rat'ttt.t’tti"".-i fl nth {Ltd c} reserpine ' J ' py tilt“ . nm . a _ e} sulfanrlamido i‘T/nrgm magi I. I a is! 13. Application of recombinant DNA technology leads to drugs that are difficult to make in the laboratory. These drugs belong to a class of compounds called a} purines in} amino acids - c} polypeptidesi'proteirts C d} steroids e} none of the above t8, 14. The following are used in recombinant DNA technology. 1 Judi-i will a?“ ' ' viii" a} Bacteria that contain plasmids. tyii‘ io]: Bacteria that do not contain piasmids, but will accept them. r" % o} Restriction endonucleases. .L a} a s c e} a. h E o 15. The majority of drugs used today were acquired by application of organic chemical synthesis. afloat. 61.111113." mp r pinna- .- Q a) TRUE fist iii? .r' n _ v_. ': flu; :"J' 1" bl FALSE F Fl'flfflxgflfipw 16. Codeine is an analgesic {pain reliever} and a cough suppressant. The development of dextromethorphan as a nonprescription cough suppressant was based on the structure of codeine. In terms of the synthesis and development of dextromethorphan as a cough suppressant. codeine served as DH CH3 '3”?! EH: OCH; codeine demon: clitorptnan a) an alkaloid from the poppy plant. b) a target compound. C c) a lead compound. . d] a derivative ot morphine. e} a at d. 1?. Development of a drug from first principles is based on studies of the biochemistry. physiology. microbiology. etc. of the problem leg. malaria} to be addressed by use ofthe drug. The purpose ofthese studies is to 75x a} ldentify a receptor {target} for the proposed drug. 13} make derivatives of a prototype drug. c} learn shoot the biology of the disease. d} decide a structure for a prototype drug based on structure—activity relationships. e) b 8t c. r1113. Select an isosteric replacement for the nitrogen atom of ephedri_ne. _a econgestant commonly found in nonprescription cold preparations. @ 19. In terms of drug design. structure-activity relationships {SARs} are used by medicinal chemists to E CH3 Wfi%——*—? Leyflfifi H I: \EHS ease Cb“ We DH EH?) 1 CH: t; this Gig v-l’rH: (gig-arms} ._ ' ' N as 9 AS w P“ G a} establish how drugs work. b} develop prototype drugs. L ' o} change a prototype structure in order to obtain the "best" drug. PW fill-1‘01 091 d} a e b e} a. b S: c 2t}. Drugs in the blood stream are generally bound to some Extent to serum proteins. e.g. serum albumin. For drug A. KD = 3 x 'lfl'E‘M: for drug B. K”: 3.6 x ‘lfl'wlvl. Q a} 1|.l'y'hen bound to serum albumin. drugs A 3. B are active at receptors. “bruit-rug A binds more strongly to serum albumin than does drug B. to) Drugs A 8: B can dissociate from complexes and be available to react with receptors. d} a 8: c ‘eLbec 2?. A second messenger that is formed inside cells from adencsine triphcsphate is a} guanosine diphosphate b} adenine diphosphate c} cyclic adenosine monophosphate C d} cyclic guanosine monophosphate e} guanosine triphosphate 28. A series of drugs D-X binds to receptors R-Y. D-Xs and KD values are: D—GGEH. soc ntvl; D-CflHg, 5 nlvl; D-CHZDH. 1oo nlvl; [fl-NH: +. see mm. The most likely bond formed between K and Y is a} icnic {electrostatic} bond b} hydrogen bond I c) hydrophobic (E, (g d) ion-reinforced hydrogen bond e) ionic bond with ‘1’ = NHa + 29. The majority of drugs. especially pharmaccdynamic drugs, form reversible, non-covalent bends with their receptors Such bends are generally weak {a few Kcalsrmole each). However. some drugs bind very strongly to their receptors because they form a} an ionic bond b} an ion-reinforced hydrogen bond A c} a hydrophobic bond d} several reversible bonds e} a hydrogen bond 3G. in a site—specific labeling experiment designed to identify a binding site amino acid of a receptor. a worker reacted a selective alkylsting agent [Ft-Br] with a receptor R, hydrolyzed the alkylated receptor A-R, isolated the amino acid and small peptides that were alkylated, and identified the following 2 substances [among others). histidinefA}; and H2153-histidinefAJI—serine—alanine—glycine-CDGH The previously determined primary amino acid sequence of the receptor indicated the following amino acid sequences: HzN—histidineiz t )-histidinet22}-serine{-23]-alanine{24}—CDDH HEN—alaninet58}-histidineffi?)rserineffiElJ-alanine(59}—lysine—CODH HgN—iysine{85}-serine{86}-alaninefB?)-alanine(3Ei}—CDDH An amino acid in the receptor binding site is. a) histidinef22} 73‘ b} histidine(5?i c} serine {231 d} serinelfifi} e) histidinet21} (9 it 33. ? 31. For reaction of a drug with its receptor to give a biologic response (BR) it can be shown that Kn = constant x therapeutic dose of drug. For several drugs that react with the same receptor this equation predicts that a} a graph of KID values plotted on the Y axis vs. doses of corresponding drugs plotted on the X axis is linear b} small values of K0 are associated with most active drugs c) large values of KD are associated with most active drugs d) a 8. b e) a 3: c 32. A "map" of a receptor binding site using a series of similar compounds that react with the receptor can be drawn based on the results of a BAR study using the same compounds. a] TRUE bi FALSE {5) Cyclooxygenase {CD-ser—DH) catalyzes the synthesis of arachidonic acid endoperoxide from arachidonic acid and oxygen. The endoperoxide is converted in several enzyme-catalyzed steps to prostaglandins that are mediators of inflammation and pain. CD—ser—DH is irreversibly inactivated by acetyl salicylic acid {aspirin}. CDgH Gift BEHIND Draw the structure of inactive CD—ser—DH. {EC}; HI" 4" (Hi 3%,.{3iifiissume that the alkaloid nicotine has the structure RSN. Complete the following equation that shows whyr solutions of nicotine are alkaline. RJN + H20 fig. Zea-“vs in H V? ' I 35. [12} Enzyme esterases, e.g. acetyl cholinesterase. and a variety of peptidases. e.g. chymotrycsin, catalyze hydrolysis of esters and amides {respectively} by the following reaction: I: E-scr—GH + Ester q—Ih— {jmmmxk—z. A + B k_ 1 kit A + [-120 —- E-ser-DH +C a) Draw the structures of A. B E C for hydrolysis of 3—{tfimethylammonioiphenyl acetate {below} catalyzed by an esterase. El} J [CHfl 3N UYCH} U a C= W [#3 defl oH ii a} a”) ‘li.‘£”3'“‘éfir'é it mac-ii C “F It H o a») D ...
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This note was uploaded on 12/16/2009 for the course MCH 311 taught by Professor Kalman during the Spring '08 term at SUNY Buffalo.

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Med Chem Exam 1_1999 - l" l a a pure drug from...

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