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Syntheses of O 6 ‐Alkyl‐ and Arylguanine Derivatives: Nucleobase Adducts Derived from Styrene 7,8‐ and 3,4‐Oxides
Author(s) -
Novák Jan,
Hasník Zbyněk,
Linhart Igor
Publication year - 2006
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200500477
Subject(s) - chemistry , styrene , styrene oxide , alkyl , adduct , medicinal chemistry , oxide , benzene , ethanol , epoxide , organic chemistry , polymer chemistry , catalysis , copolymer , polymer
A series of O 6 ‐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)