Page 69 - Medicinal Chemistry Self Assessment

58 Medicinal Chemistry Self Assessment

564
739
2. The glucocorticoids interact with residues within the glucocorticoid receptor (Arg , Asn , Thr ,
611
642
570
Gln , and Gln ) via hydrogen bonding and ion–dipole interactions at physiological pH (7.4). Iden-
tify which functional groups could interact with the side chains of these amino acids.
Can Interact with
Can Interact with Glutamine and
642
Asparagine and Threonine 739 Glutamine via a
564
570
Can Interact with Arginine via a Hydrogen Bonding Hydrogen Bonding
611
via an Ion–Dipole Interaction Interaction Interaction
Functional
Group Yes or No Yes or No Yes or No
A 1.17 and 2.17 – remove bold from label
B
C
D E
E C
F
F
B
3. Several of the functional groups identified in the structure evaluation grid are essential for biological
activity. There are several metabolic transformations that render the glucocorticoids inactive. These
D
A
transformations include the following:
1. Ring A ketone reduction
Hydrocortisone
2. Ring A double bond reduction

3. C-17 oxidation
Question #3 structure needs to be replaced:
4. C-11 oxidation

21

11 17

A

Based on this information, consider the array of products drawn in the scheme that follows. Iden-

tify each type of reaction or transformation that has occurred and evaluate each of the products to
1.18 and 2.18 – remove bold from label
determine if each product is active or inactive.

E
A I C D O
H O I
OH
NH
I O 2
B I

L-Thyroxine