Page 86 - Medicinal Chemistry Self Assessment

Section 2 Whole Molecule Drug Evaluation

1.23 Quinapril

1.23 Quinapril
Shown below is the structure of quinapril. It is an angiotensin converting enzyme (ACE) inhibitor that is used in the
Shown below is are identified.
treatment of hypertension and heart failure. Five functional groups are identified.

B
H 3 C

O O D
A O
H
N
N
C
CH 3
O
OH
E

1. Using the table if it is hydrophilic or hydrophobic in brief explanation for your response.
1. Using the table below, identify the five boxed functional groups. For each of the functional groups you
identified, indicate if it is hydrophilic or hydrophobic in character. Also provide a brief explanation for
2. Using the ionized or unionized at pH environments of 1.5, 4.8, 6.3, 7.4, and 8.1.
your response.
3.
Answer
CH 3
Functional Group Name Hydrophilic or Hydrophobic
A O O
B O
C H
N
D N
E CH 3
O
OH

2. Using the unmodified structure of quinapril and the following table, identify all of the acidic and basic

functional groups present in the structure, provide the normal pK range for each functional group, and
a
identify if each functional group would be primarily ionized or unionized at pH environments=1.5, 4.8, 6.3,
7.4, and 8.1.

4. Quinapril is a is administered orally instead of quinaprilat.

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Quinapril Quinaprilat