Side effects might also be reduced or eliminated by varying apparently harmless substituents. For example, the halogen substituents of the antifungal agent UK 47265 were varied i order to find a compound that was less toxic to the liver. This led to the successful antifungal agent fluconazole. N. N. OH N' OH N UK 47265 Fluconazole

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
Chapter19: Enolate Anions And Enamines
Section: Chapter Questions
Problem 19.48P
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In the two compounds below::

what the difference between cl and F in toxicity?

why replacing the cl with F render the compound less toxic? ( they both electron withdrawing group)

Side effects might also be reduced or eliminated by varying
apparently harmless substituents. For example, the halogen
substituents of the antifungal agent UK 47265 were varied in
order to find a compound that was less toxic to the liver. This
led to the successful antifungal agent fluconazole.
OH
OH
.CI
UK 47265
Fluconazole
* 46
Transcribed Image Text:Side effects might also be reduced or eliminated by varying apparently harmless substituents. For example, the halogen substituents of the antifungal agent UK 47265 were varied in order to find a compound that was less toxic to the liver. This led to the successful antifungal agent fluconazole. OH OH .CI UK 47265 Fluconazole * 46
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