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

08:00 EDT 16th May 2019 | BioPortfolio

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

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 (PPG). 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.


Journal Details

This article was published in the following journal.

Name: The Journal of organic chemistry
ISSN: 1520-6904


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Medical and Biotech [MESH] Definitions

An aromatic ketone containing the aniline structure (ANILINE COMPOUNDS).

A drug-metabolizing, cytochrome P-450 enzyme which catalyzes the hydroxylation of aniline to hydroxyaniline in the presence of reduced flavoprotein and molecular oxygen. EC 1.14.14.-.

Complex pharmaceutical substances, preparations, or agents of organic origin, usually obtained by biological methods or assay. They are used especially in diagnosis and treatment of disease (as vaccines or pollen extracts). Biological products are differentiated from BIOLOGICAL FACTORS in that the latter are compounds with biological or physiological activity made by living organisms. (From Webster's 3d ed)

Drugs whose drug name is not protected by a trademark. They may be manufactured by several companies.

A plant genus of the family RUTACEAE. Members contain quinoline alkaloids.

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