Page 73 - Medicinal Chemistry Self Assessment

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1. Conduct a structural evaluation of that follow.
E
A I C D O
H O I
OH

I 62 Tri-iodothyronine NH 2
O
Medicinal Chemistry Self Assessment

B I

2. Hormone replacement therapy in the form of levothyroxine (T ) is available for those patients who
1.18 and 2.18 – remove bold from label <DAVID_-change caption to Levothyroxine>
L-Thyroxine (T )
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do not produce an adequate endogenous supply of T . Evaluate the structure of levothyroxine and
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determine if it is an enantiomer, diastereomer, or geometric isomer.

O
I
2. Hormone replacement therapy in the geometric isomer. O
H
N
2
H OH I H O I O OH
H
H O I I O OH NH 2
OH H I NH
I O 2
L-Tyrosine Levothyroxine
I

Levothyroxine

3. Evaluate the chiral carbon atom in levothyroxine to determine if this drug is drawn as the R- or
S-enantiomer.

3. Evaluate the chiral to determine if this drug is drawn as the R- or S-enantiomer.
4. T is the biologically active hormone. It interacts with the thyroid hormone receptor via hydrogen
bonding, ion–dipole, hydrophobic, and ionic interactions. Evaluate the ribbon diagram that shows
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4. T 3 is the in the structure evaluation grid.
how T interacts with the surface of the thyroid receptor and identify the types of interactions
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possible for each of the five functional groups identified in the structure evaluation grid.

I O
H O I
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OH
H
NH
O1.18 and 2.18 – remove bold from label
2

I

Tri-iodo-L-thyronine

Tri-iodothyronine

Tri-iodothyronine

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5. T is biosynthesized from L-tyrosine within the thyroglobulin molecule and is considered an amino
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acid–based hormone. Other hormones in the body are steroid-based (e.g., estrogen) or peptide-

1.18 and 2.18 – remove bold from label
based (e.g., insulin). Evaluate the structure of T and justify its classification as an amino acid–based

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O
hormone by determining which functional groups are derived from L-tyrosine.
I O
H 2 N OH O I
H H O I OH O
H 2 N OH I
H I H O O H NH 2 OH
OH I H NH 2
I O
L-Tyrosine OH Levothyroxine I

L-Tyrosine Levothyroxine