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CHE130A Final Practice W07 Key Hague

CHE130A Final Practice W07 Key Hague - Chem 130A Winter...

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(1) (35 points total) Shown below is posaconazole, an antifungal drug that was approved by the FDA in September, 2006. Chem 130A, Winter 2007, Practice Final _______________________________ name (a) (5 points) Please label all good hydrogen-bond acceptors in posaconazole. (b) (5 points) Please label all good hydrogen-bond donors in posaconazole. (c) (5 points) Please point out a region of posaconazole that is hydrophobic. (d) (10 points) Please suggest a modification to posaconazole that will improve the ability of its difluorobenzene ring to participate in cation• ! interactions. Explain your reasoning a n d discuss the potential problems associated with making such a change. N N O N N N OH O N N N F F O HBA (both lone pairs) HBD key HBA (both lone pairs) HBA HBA HBA (both lone pairs) HBA HBA HBA (only if not protonated; note that their H-bonding ability is also modulated by the attached aromatic rings to which they are slightly conjugated) N N O N N N OH O N N N O Removing the F's will increase the electron density on the face of the aromatic ring. • This change could disrupt binding if this ring was involved in ! -stacking (charge transfer) interactions. • Removal of the F's also has a small effect on the steric profile of the ring. • Without the F's, the ring will be more susceptible to being metabolized through hydroxylation. hydrophobic HBA HBD
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(e) (10 points) Please identify one potentially toxicophoric group in posaconazole molecule a n d describe the potential toxic chemistry you expect it to undergo. Chem 130A, Winter 2007, Practice Final _______________________________ name N N O N N N OH O N N N F F O key This ring may bind to and inhibit cytochrome P450's or be otherwise involved in undesirable interactions with metals.
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