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Chapter 3: Problem 7

Design conformationally-rigid analogs for: a. 4 -aminobutyric acid (GABA) b. Epinephrine c. Nicotine

Short Answer

Expert verified
Rigid analogs for GABA, epinphrine, and nicotine could be designed by making changes to their original structures that restrict the free rotation of bonds, such as by introducing or modifying cyclic structures. The resulting analogs would have increased conformational rigidity.

Step by step solution

01

- Design rigid analog for GABA

For 4-aminobutyric acid (GABA), a conformationally-rigid analog could be achieved by introducing a cyclic structure. Start by creating a bond between the NH2 group and the terminal carbon on the 4-carbon chain. This will lead to the formation of a 5-membered ring compound that would restrict the rotation and increase the rigidity of the molecule.
02

- Design rigid analog for Epinephrine

For epinephrine, a conformationally-rigid analog could be formed by turning the chain linking the catechol ring and the amine into a rigid group such as a cyclohexyl ring. By replacing the −CH2−CH2−NH2 with a −(CH2)3− ring, the molecule becomes rigid as the free rotation around the bond has been restricted.
03

- Design rigid analog for Nicotine

Nicotine has a rigid bicyclic structure, so to create a conformationally-rigid analog, the Pyrrolidine ring could be replaced with a piperidine ring to restrict the free rotation of chemical bonds. It could further be fused to another aromatic ring to ensure maximized rigidity.

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Most popular questions from this chapter

Draw a dose-response curve for: a. a full agonist b. a mixture of a full agonist and a competitive antagonist

An isosteric series of compounds shown below, where \(\mathrm{X}=\mathrm{CH}_{2}, \mathrm{NH}, \mathrm{O}, \mathrm{S}\), was synthesized. The order of potency was \(\mathrm{X}=\mathrm{NH}>\mathrm{O}>\mathrm{S}>\mathrm{CH}_{2}\). How can you rationalize these results (you need to consider the threedimensional structure)?

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