CHE130A MT1 W07 Key Hague

CHE130A MT1 W07 Key Hague - Chem 130A, Winter 2007, Midterm...

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(1) (10 points) Shown below are the structures of several compounds that are known to inhibit the enzyme known as HIV integrase, a key enzyme in the replication cycle of HIV. Chem 130A, Winter 2007, Midterm _______________________________ name (a) Please propose a model of the pharmacophore that is connected to the activity of these compounds. O O OH OH O O OH HO O OH HO O HO 2 C HO 2 C HO OH O N H OH OH O N H key O Based on the features that these compounds have in common, a reasonable model of the pharmacophore is: hydrophobic/ aromatic linker carbonyl catechol (i.e. dihydroxybenzene) linker OH OH
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(2) (65 points total) Shown below is dirlotapide—the active ingredient in slentrol TM , a "selective microsomal triglyceride transfer protein inhibitor" that is "indicated for the management of obesity in dogs". Chem 130A, Winter 2007, Midterm _______________________________ name (a) (5 points) Please label all stereocenters in dirlotapide with appropriate R / S labels. (b) (5 points) Please label all good hydrogen-bond acceptors in dirlotapide. (c) (5 points) Please label all good hydrogen-bond donors in dirlotapide. (d) (5 points) Please label all rings in dirlotapide that could participate in cation• ! interactions. (e) (10 points) Please suggest a modification to dirlotapide that would increase its logP. Explain
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CHE130A MT1 W07 Key Hague - Chem 130A, Winter 2007, Midterm...

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