Problem 3 A rotatable bond is defined as any single non-ring bond, attached to a

Question

Problem 3 A rotatable bond is defined as any single non-ring bond, attached to a non-terminal. non-hydrogen atom. Amide C-N bonds are typically not counted because of their high barrier to rotation Remember delta G = delta H ? T delta S! A molecule will have to adopt a fixed conformation to bind to an enzyme or receptor, or to pass through a membrane (bioavailability) This involves a loss in entropy, so if the molecule is more rigid to start with, less entropy is lost. Determine the number of rotatable bonds in the ii-blockers shown below. Which drug would you expect to have better bioavailability? Based on the compounds below. Explain why rigid analogous may not always be more potent or efficacious than the more flexible analogue

Explanation / Answer

1) first compound has four rotable bonds, second compound hac three rotable bonds

so second conformer is more bioavilable, more rigid

2) first compound is more flexible because it has more rotable bonds

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