Page 16 - Medicinal Chemistry Self Assessment

3. Shown below is the structure of imipramine as well as three analogs. Evaluate each analog and provide an
overall evaluation of how each change will affect the chemical properties of imipramine.

1.1 Functional Group Characteristics and Roles 5

3. Shown below is the structure of imipramine as well as three analogs. Evaluate each analog and
N
provide an overall evaluation of how each change will affect the chemical properties of imipramine.

CH
Imipramine N 3
CH 3

Imipramine
N N N
Cl CH
3
O
CH CH
N 3 N 3 N CH 3
Analog A CH 3 Analog B CH 3 Analog C CH 3

Analog A Analog B Analog C

4. Shown below is the structure of a tetrapeptide that is part of a larger protein receptor. The side chains of the

four amino acids have been boxed.
4. Shown below is the structure of a tetrapeptide that is part of a larger protein receptor. The side
chains of the four amino acids have been boxed.

O NH
O 2
O OH O
H
N N R
R 1 N H N 2
H H
O O

H O

a. Identify the four amino acids that comprise this tetrapeptide sequence.

b. For each amino acid, identify the key chemical properties of its highlighted side chain.

Answers can be found in Section 2.1 [this will be linked to section 2.1 title] Page 2 of 2

Note: The questions in this chapter are related to Chapter 2 in Harrold MW and Zavod RM, Basic Concepts in
Medicinal Chemistry, American Society of Health-System Pharmacists, ©2013.

Page 2 of 2