Prodrugs for targeting hypoxic tissues: Regiospecific elimination of aspirin from reduced indolequinones

A series of regioisomeric derivatives of a 1-methylindole-4,7-dione were synthesised, substituted with a 2-acetoxybenzoate leaving group linked through the (indol-2-yl)methyl or (indol-3-yl)methyl (or propenyl) positions. Reductive elimination of the leaving group occurred from the (indol-3-yl)methy...

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Veröffentlicht in:Bioorganic & medicinal chemistry letters 1999-01, Vol.9 (1), p.113-118
Hauptverfasser: Jaffar, M, Everett, S.A, Naylor, M.A, Moore, S.G, Ulhaq, S, Patel, K.B, Stratford, M.R.L, Nolan, J, Wardman, P, Stratford, I.J
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Sprache:eng
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Zusammenfassung:A series of regioisomeric derivatives of a 1-methylindole-4,7-dione were synthesised, substituted with a 2-acetoxybenzoate leaving group linked through the (indol-2-yl)methyl or (indol-3-yl)methyl (or propenyl) positions. Reductive elimination of the leaving group occurred from the (indol-3-yl)methyl derivatives but not the 2-substituted regioisomers, indicating that only the C-3 position may be utilised in bioreductively-activated drug delivery, which was demonstrated with an aspirin prodrug. Graphic
ISSN:0960-894X
1464-3405
DOI:10.1016/S0960-894X(98)00695-7