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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

Chemistry
Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
Section: Chapter Questions
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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Propose a synthesis for esmolol from 4-hydroxycinnamic acid, epichlorohydrin, and isopropylamine

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
Transcribed Image Text: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
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