Med Chem Exam 1 1999

Med Chem Exam 1 1999 - [D i”; Name

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Unformatted text preview: [D i”; Name —'-——_—..-.-—-.-.—.-._—-.— Student No. Medicinal Chemistry 311 October '5. 1999 Examination #1 Use your B-digit person number. lease the last [Elthi space blank. For the multiple choice questions. s_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 aidiscoyer. design Eisynthesize drugs. ES organic iilririirriiit i011} training b) design 3: make drug dosage forms. e.g. tablets. r“ . , j . . . . . - Lu. iTUJLlE c] are Inorganic chemists by training. [darihl'il CU --1 d) primarily study the effects of drugs in the body. e) a at c r")- . .E-l' .I‘j LIL ’1 .II- For questions 2 8c 3. select the appropriate person and enter the appropriate fl $10] ff letter on the bubble sheet: a} Friedrich Wohler. b} Friedrich Serturner. c] John Abel. d} F'aul Ehrlich. e} William 1li'iiithering 9"” d . .mgw ‘H F. L25:- Wd’ii (if -+ lg" E’CthllJiifll-"i ci'rlllliiif i.l»;iir“ri.i._-"rr'I.l-r {Emmi-ii? Airs-{L 2. The German pharmacist who was the first person to publish—on the-isolation of a pure drug from plants. {Earlier-rte?) Limes-lily- um-iaaearl. a? 3. His statement of the principles of chemotherapy included the ideas that nor be chemotherapeutic drugs would have relatively low molecular weights {compared to proteins} and would act directly on parasites. LL}. E'1q.’i1li: i1 4. In the % resistance to chemotherapeutic drugs is especially a problem when treating infections caused by _ Hacie- i or. ii i ir. r‘. l- i. i- iii 3) mfllflfi- {T i fr [ii if ii; T'i"'5.{Tl1L' b}fungl. I 1- |_.»_.1EU~r_-.f _.: l." 'a'phr-Ifi—firkji. 1 C c} bacteria. ' L d} protozoans. e.g. malarial parasites. e} a 3: c 5. Examples of classes of drugs that are made by plants are “Pit 16rd if? . f'l'tr' FAN. if} '1' ..”.-l~.'(.r' aialkaloids. e.g. codeine. OH 5 "fl- gc'i' 'L‘T.‘ *“ b} purines. e.g. theophylline and cafieine. M”. 3” E_ c} cardiac glycosides {steroidal sugars). e.g. digoxin " d} b 3: c. e} a. b. 3: c. 6. 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 -.I’"\- 'r'. A structural feature of alkaloids is the (O A _ - IL.-x it‘d“? 3} alcohol {nflHi group. ” fa.“ bra}- b} carboxylic acid {-CDDH) group. #0“ c) ester {-CDDR} group. d) amide (-CDNHE} group. e) amine (-N=] group. 8. Drugs from natural sources such as plants may be discovered through if. a) screening programs. b) toxicity.Ir reports. c) ethnopharmacologvrfolklore. d} b 3: c e} a. b 8: c Q. Drugs obtainable from mammalsfanimals include C .r I'A-Il a} penicillin. I __fifl.I..ll~jii‘t:-” 1” b) estrogens. ll‘FWG'dE “it “E715 c} insulinrwk it?!“ d} b e 0 finale; r} e} a. b 3: c Harm-m, 1f]. The following structure is .3“! DH "L. .-- r: i 'IH-Ifjrdjr' if) :1' .13 1"Ill'"~[_j!"'~' HU C a} an alkaloid b) a polypeptide c) a steroid -—-ar d) a purine e) none of the above . f. In fit)!" 1"] . - .' . . -- \.r~ If tutitxeareaiw F-L’I‘l’lUlC-LI'DPF‘lflfi'fl_f7f'f'*er 1* 41' VI ' J 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 purifyr the potential drugs contained in the extracts and characterize them usingr e.g.. ultraviolet, infrared and visible spectroscopv. nuclear magnetic resonance spectrometrv, X-l‘ay crystallographv. a) TRUE b] FALSE 12. An example of an antibiotic (obtained from naturer by definition) is ‘atLurea - a Hr e .. r Fr l 1- - J“. I 'I \LP-fvl'di‘J-I) w I. b} tetracycine a» t: :_. {—Lidjiil-g rr . (“slag-.1.- “NH-mg in.— c] reserpine " a pay on Eli-fig moodeine L {mm 1 H1. . ' ' e} sulfanilamide I“ gram {mild __I 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 b} amino acids c} polypeptideslproteins C d} steroids e} none of the above - 3 ii 14. The following are used in recombinant DNA technology. . ilfi‘e' at?” as“ [Ls-v?” a} Bacteria that contain plasmids. E} ’ b) Bacteria that do not contain plasmids. but will accept them. c} Restriction endonucleases. 23...; — d} a 8: c e) a. b a c \‘x 15- The major“? 0f drugs “sad today were acquired by application of organic chemical synthesis. I difltti Iiz'tflg- fi'itirpj’lfli'x I a) {if-:1 .' Ill G)? b} FALSE {t’ieper idJHL EFL I: v 's msgfiséo: 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 cHJ CH3 0|: H 3 OCH 3. codeine deadrorn emorpnan a) an alkaloid from the poppy plant. b) a target compound. 6‘ c) a lead compound. d} a derivative ot morphine. | 16. Codeine is an analgesic {pain reliever} and a cough suppressant. The e} a 8: d. 1?. Development of a drug from first principles is based on studies of the biochemistryr physiology. microbiology. etc. of the problem leg. malaria} to be addressed by use of the drug. The purpose of these studies is to a} identify a receptor (target) for the proposed drug. it} make derivatives of a prototype drug. c} learn about the biology of the disease. d} decide a structure for a prototype drug based on structure—activity relationships. E} b 8; c. '13. Select an isosteric replacement for the nitrogen atom of ephedri_ne._a econgestant commonly found in nonprescription cold preparations. CHS — " 9" 33; Li}; 1013' I: C i. I EH3 i was so so; ! DH (EH?) 1 _ - .:_ t U:{';'lli' _l_h___ I. _ @— c- H I . 1 19. In terms of drug design, structureaactivity relationships {SARs} are used byN medicinal chemists to a] establish how drugs vvork. t; 3w b} develop prototype drugs. {tit} _ WE ' c} change a prototype structure in order to obtain the “best” drug. pi}; ' t_' d} a 3i b e} a. b 3: c 2D. Drugs in the blood stream are generally bound to some extent to serum proteins. e.g. serum albumin. For drug A. Ko = 3 x “lfl'sl‘vl; for drug E, K“: 3.6 x it)” M. a} 1|.l'ilhen bound to serum albumin. drugs A 8. B are active at receptors. l_ “bpflrug A binds more strongly to serum albumin than does drug B. to} Drugs A & B can dissociate from complexes and be available to react "- with receptors. d}-a '8: c ‘oLbEcc 2?. A second messenger that is formed inside cells from adenosine triphosphate 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-CGEH, Silt] nlyl; D-GfiHisi 5 nlyl; D-CHZDH. 1GB oM; Iii-NH3 +, 290 nitii. The most likely bond formed between K and Y is a} ionic {electrostatic} bond bi hydrogen bond 5} hydrophobic [E d) ion-reinforced hydrogen bond e) ionic bond with Y = NH3 + 29. The majority of drugs. especially pharmacodynamic drugs, form reversible, non-coyaient bonds with their receptors. Such bonds are generally weak {a few Kcalsi'mole each). Howeyerr 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} seyeral reyersible 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 alkylating agent [HEW] with a receptor R. hydrolyzed the alkyiated receptor A-R, isolated the amino acid and small peptides that were alkylated, and identified the following 2 substances {among others}: histidinetA}; and HEN-histidinefAl—serine—alanine—glycine-CUDH The previously determined primary amino acid sequence of the receptor indicated the following amino acid sequences: HEN—histidinei2il-histidine{221|-serioei23i-aianinei24l—CDDH H2N—a|anine{55}-histidine[5?)rserine(53}uaIanineIESQJ—lysine—CDDH H2N—|ysine{35)-serine{86}-alaninefd?)-alanine(33}—CDOH An amino acid in the receptor binding site is, a) histidinef22} b} histidineffi?) ’ c} serine [23] d} serineiEEii e} histidineth} ? 31. For reaction of a drug with its receptor to give a biologic response (BR) it can be shown that Kn = constant it therapeutic dose of drug. For several drugs that react with the same receptor this equation predicts that a} a graph of VIEI values plotted on the Y axis vs. doses of corresponding drugs plotted on the X axis is linear b} small values of KD are associated with most active drugs c) large values of KD are associated with most active drugs 0 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 EAR study using the same compounds. a] TRUE hi FALSE 33. {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}. ECIgH Jig/WEE Ha ii- 0 x".- aspirin Draw the structure of inactive CD—ser—DH. rm ' a - _ - {if} g at (Warm g —-s<r~.o -— :1: a ' mg; lam-r5 HRH_ Assume that the alkaloid nicotine has the structure RSN. Complete the following equation that shows whyr solutions of nicotine are alkaline. R3N '+ H20 K3 Jig-Hi if? or” !-" or" HIM—.43 . x— .z'-|-._Ii-"" {M 35. {12} Enzyme eeteraaea. eg. acetyl chclineeteraae. and a yariety ct ceptidaeee. eg. chymctrypetn, catalyze hydrclyete ct esters and amides [reapectiyelytt by the fcllcwing reaction: k2 k E-SEI-UH 4' Efitfil' w—l“— Cgmplex—h A + B 11-1 A + H20 £- E-scr-CIH+C a) Draw the atructuree cf A, B 8; C fcr hydrolysis cf 3—{trimethylammcnictphenyl acetate {below} catalyzed by an eateraae. [EB t‘ {(3143);}: 0"? CH3 E J c I. . ...
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Med Chem Exam 1 1999 - [D i”; Name

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