Chapter 20
An Introduction to Medicinal Chemistry · 3 exercises
Problem 5
Show the mechanism by which the prodrugs tenofovir disoproxil and adefovir dipivoxil are converted to their active forms. Why are extended esters used as prodrugs for these compounds?
4 step solution
Problem 6
Most PIs bind to the active site with a water molecule acting as a hydrogen bonding bridge to the enzyme fl aps. Suggest what relevance this information might have in the design of novel PIs.
5 step solution
Problem 8
Capravirine is a third-generation non-nucleoside reverse transcriptase inhibitor (NNRTI) with a side chain that takes part in important hydrogen bonding to Lys-103 and Pro236 in the allosteric binding site, yet the side chain has a carbonyl group. Discuss whether this makes the structure prone to enzymatic hydrolysis and inactivation.
5 step solution