Photorearrangement of Quinoline-Protected Dialkylanilines and the Photorelease of Aniline-Containing Biological Effectors

Davide Deodato, Naeem Asad, Timothy M. Dore

Research output: Contribution to journalArticlepeer-review

Abstract

The direct release of dialkylanilines was achieved by controlling the outcome of a photorearrangement reaction promoted by the (8-cyano-7-hydroxyquinolin-2-yl)methyl (CyHQ) photoremovable protecting group. The substrate scope was investigated to obtain structure-activity relationships and to propose a reaction mechanism. Introducing a methyl substituent at the 2-methyl position of the CyHQ core enabled the bypass of the photorearrangement and significantly improved the aniline release efficiency. We successfully applied the strategy to the photoactivation of mifepristone (RU-486), an antiprogestin drug that is also used to induce the LexPR gene expression system in zebrafish and the gene-switch regulatory system based on the pGL-VP chimeric regulator in mammals.

Original languageEnglish (US)
Pages (from-to)7342-7353
Number of pages12
JournalJournal of Organic Chemistry
Volume84
Issue number11
Early online dateMay 16 2019
DOIs
StatePublished - Jun 7 2019

ASJC Scopus subject areas

  • Organic Chemistry

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