Synthesis of 7-hydroxy(phenyl)ethylguanines by alkylation of 2-amino-6-chloropurine with allyl-protected bromohydrins.
Protecting the hydroxyl group in both 2-bromo-2-phenylethanol and 2-bromo-1-phenylethanol enhanced the alkylation of 2-amino-6-chloropurine to give corresponding 7- and 9-alkylated products. Subsequent hydrolysis and deprotection led to 7- and 9-hydroxy(phenyl)ethylguanines. 7-Hydroxy(phenyl)ethylguanines are major guanine adducts formed by interaction of styrene 7,8-oxide with DNA.
Novák
Jan
J
Department of Organic Chemistry and Central Laboratories, Institute of Chemical Technology, Prague, Technická 1905, CZ-166 28 Prague, Czech Republic.
Linhart
Igor
I
Dvoráková
Hana
H
Kubelka
Vladislav
V
D015075:2-Aminopurine / Q000031:analogs & derivatives* / Q000737:chemistry*; D000438:Alcohols / Q000737:chemistry*; D000478:Alkylation; D000498:Allyl Compounds / Q000737:chemistry*; D018736:DNA Adducts / Q000737:chemistry; D006147:Guanine / Q000031:analogs & derivatives* / Q000138:chemical synthesis
D000438:Alcohols; D000498:Allyl Compounds; D018736:DNA Adducts; C023963:bromohydrins; D015075:2-Aminopurine; D006147:Guanine; C040510:2-amino-6-chloropurine