Organic Chemistry

1228 CHAPTER 30 The Organic Chemistry of Drugs

8. The following compound is a suicide inhibitor of the enzyme that catalyzes amino acid racemization:

Propose a mechanism that explains how this compound irreversibly inactivates the enzyme.

9. Explain how each of the antiviral drugs shown in Section 30.12 differs from the naturally occurring nucleoside that it most closely
   resembles.


10. Show a mechanism for the formation of a benzodiazepine 4-oxide from the reaction of a quinazoline 3-oxide with methylamine.


11. Show how could be synthesized from benzoyl chloride,para-chloroaniline, methyl iodide, and the ethyl ester of glycine.


12. Show how could be synthesized from the indicated starting materials.

CH 3 NH 2

SCH 3

NHCH 3

CH 3 S

N

N

H

CH 2 OH

CH 3

N

N

H

CH 2 CH 2 SCH 2 CH 2 NH

CH 3

CN

N

C

CN

N

C

++HSCH 2 CH 2 NH 2

+

Tagamet®

O

C O

C

NH 2

Cl

Cl

Cl

++

+ CH 3 I

Valium

N

N

O

CH 3

H 2 NCH 2 OCH 2 CH 3

Valium®

HC CCHCO−

NH 2

O

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