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Controlling the rates of reductively-activated elimination from the (indol-3-yl)methyl position of indolequinones

Abstract:

A series of substituted 3-(4-nitrophenyloxy)methylindole-4,7-diones (Q) were synthesised. The effects of substitution patterns on the indole core on rates of elimination of 4-nitrophenol as a model for drug release following fragmentation of a phenolic ether linker were studied. After reduction to either the radical anion (Q·-) or hydroquinone (QH2) elimination of 4-nitrophenol occurred from the (indol-3-yl)methyl position. The half-lives of Q·- radicals at [O2] ≈ 5 μmol dm-3, typical of tumo...

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Publication status:
Published

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Publisher copy:
10.1039/b009652k

Authors


Everett, SA More by this author
Naylor, MA More by this author
Barraja, P More by this author
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Journal:
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2
Issue:
5
Pages:
843-860
Publication date:
2001
DOI:
EISSN:
1364-5471
ISSN:
1472-779X
URN:
uuid:3d1ddd7a-a6dd-47d0-9c75-37dedecad673
Source identifiers:
131521
Local pid:
pubs:131521
Language:
English

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