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Full Paper
Syntheses of O6-Alkyl- and Arylguanine Derivatives: Nucleobase Adducts Derived from Styrene 7,8- and 3,4-Oxides
Article first published online: 9 NOV 2005
DOI: 10.1002/ejoc.200500477
Copyright © 2006 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Additional Information
How to Cite
Novák, J., Hasník, Z. and Linhart, I. (2006), Syntheses of O6-Alkyl- and Arylguanine Derivatives: Nucleobase Adducts Derived from Styrene 7,8- and 3,4-Oxides. Eur. J. Org. Chem., 2006: 507–515. doi: 10.1002/ejoc.200500477
Publication History
- Issue published online: 2 JAN 2006
- Article first published online: 9 NOV 2005
- Manuscript Received: 28 JUN 2005
Vol. 2006, Issue 16, 3771, Article first published online: 10 JUL 2006
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Keywords:
- Alkoxypurines;
- Aryloxypurines;
- DNA adducts;
- DNA damage;
- Heterocycles
Abstract
A series of O6-alkyl and -arylguanine derivatives that may be formed in vivo after exposure to styrene has been prepared by reaction of 6-(4-aza-1-azoniabicyclo[2.2.2]octyl)-purine with alkoxides and aryloxides, respectively. Themonoprotected diols 2-allyloxy- or 2-benzyloxy-1-phenylethanol and 2-allyloxy- or 2-benzyloxy-2-phenylethanol were used as synthetic equivalents of styrene 7,8-oxide. 4-Vinylphenol, 2-(4-hydroxyphenyl)ethanol and 4-hydroxyphenylacetic acid were used as synthetic equivalents of arene oxide metabolites of styrene, i. e., styrene 3,4-oxide, 4-(2-hydroxyethyl)benzene 1,2-oxide and 4-carboxymethylbenzene 1,2-oxide, respectively. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)