Organic Chemistry

Problems 1227

Key Terms

antiviral drug (p. 1225)

bactericidal drug (p. 1212)

bacteriostatic drug (p. 1212)

biological activity (p. 1221)

blind screen (p. 1211)

brand name (p. 1207)

combinatorial organic synthesis (p. 1223)

distribution coefficient (p. 1222)

drug (p. 1204)

drug resistance (p. 1220)

drug synergism (p. 1219)

generic name (p. 1208)

lead compound (p. 1208)

molecular modeling (p. 1223)

molecular modification (p. 1208)

orphan drug (p. 1226)

proprietary name (p. 1207)

quantitative structure–activity

relationship (QSAR) (p. 1222)

random screen (p. 1211)

rational drug design (p. 1221)

receptor (p. 1214)

suicide inhibitor (p. 1218)

therapeutic index (p. 1220)

trademark (p. 1207)

trade name (p. 1207)

Problems

1. What is the chemical name of each of the following drugs?
   a. benzocaine
   b. procaine


2. Based on the lead compound for the development of procaine and lidocaine, propose structures for other compounds that you
   would like to see tested for use as anesthetics.


3. Which of the following compounds is more likely to exhibit activity as a tranquilizer?


4. Which compound is more likely to be a general anesthetic?


5. What accounts for the ease of imine formation between penicillinase and the sulfone antibiotic that counteracts penicillin
   resistance?


6. For each of the following pairs of compounds, indicate the compound that you would expect to be a more potent inhibitor of
   dihydrofolate reductase:
   a.

b.

7. The lethal dose of tetrahydrocannabinol in mice is and the therapeutic dose is The lethal dose of sodium
   pentothal in mice is 100 mg>kg,and the therapeutic dose is 30 mg>kg.Which is the safer drug?

2.0 g>kg, 20 mg>kg.

CH 2 CHCH 3

CH 3

H 2 N N

CH 2 CH 3

N or

NH 2

H 2 N N

CH 3

CH 2 CHCH 2 CH 3

CH 3

N

NH 2

H 2 N N

Cl

or

N

NH 2

H 2 N N

NO 2

CH 2 CHCH 3

CH 3

CH 2 CHCH 3

CH 3

N

NH 2

CH 3 CH 2 CH 2 OH or CH 3 OCH 2 CH 3

CH 3 O Nor

O

N

CH 3 C N

O

CH 3

N

CH 3

O

AU: Add terms to list?

or change to lightfacein text?

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