In certain clinical situations, there is need for an injectable B-blocker with a short biological half-life. The clue to development of such a drug was taken from the struc- ture of atenolol, whose corresponding carboxylic acid (the product of hydrolysis of its amide) has no B-blocking activity. Substituting an ester for the amide group and lengthening the carbon side chain by one methylene group resulted in esmolol. Its ester group is hydrolyzed quite rapidly to a carboxyl group by serum esterases under physiological conditions. This hydrolysis product has no B-blocking activity. OMe + CI HO NH2 4-Hydroxycinnamic acid Esmolol Isopropyl- amine Epichloro- hydrin

In certain clinical situations, there is need for an injectable B-blocker with a short biological half-life. The clue to development of such a drug was taken from the struc- ture of atenolol, whose corresponding carboxylic acid (the product of hydrolysis of its amide) has no B-blocking activity. Substituting an ester for the amide group and lengthening the carbon side chain by one methylene group resulted in esmolol. Its ester group is hydrolyzed quite rapidly to a carboxyl group by serum esterases under physiological conditions. This hydrolysis product has no B-blocking activity. OMe + CI HO NH2 4-Hydroxycinnamic acid Esmolol Isopropyl- amine Epichloro- hydrin

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter21: Benzene And The Concept Of Aromaticity

Section: Chapter Questions

Problem 21.60P

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