Alkylation of 9-substituted guanine derivatives with ,-dihaloalkanes

Reactions of 9-substituted guanine derivatives with NaH/1,2-dibromoethane, 1,3-dibromopropane, or 1,4-dibromobutane at room temperature resulted in the isolation of tricyclic 1,N-2-(1,2-ethano)guanine, 1,N-2-(1,3-propano)guanine, or 1,N-2-(1,4-butano)guanine products, respectively. O-6-Haloalkyl and...

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Bibliographic Details
Published inHeteroatom chemistry Vol. 28; no. 5
Main Authors Framski, Grzegorz, Goslinski, Tomasz, Januszczyk, Piotr, Golankiewicz, Bozenna, Ostrowski, Tomasz
Format Journal Article
LanguageEnglish
Published HOBOKEN Wiley 01.09.2017
Hindawi Limited
Subjects
Alkylation
Chemistry
Chemistry, Multidisciplinary
Derivatives
Dimers
Physical Sciences
Science & Technology
DNA-ADDUCTS
CROSS-LINK
SITE-SPECIFIC SYNTHESIS
CHEMICAL CARCINOGENESIS
ACROLEIN
1,N2-PROPANODEOXYGUANOSINE ADDUCTS
N1-guanine substitution
nucleoside dimers
ACYCLOVIR
tricyclic guanine
PHYSIOLOGICAL CONDITIONS
dihaloalkanes
ANTIVIRAL ACTIVITY
2'-DEOXYGUANOSINE
O6-guanine substitution
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Summary:Reactions of 9-substituted guanine derivatives with NaH/1,2-dibromoethane, 1,3-dibromopropane, or 1,4-dibromobutane at room temperature resulted in the isolation of tricyclic 1,N-2-(1,2-ethano)guanine, 1,N-2-(1,3-propano)guanine, or 1,N-2-(1,4-butano)guanine products, respectively. O-6-Haloalkyl and N1-haloalkyl products were obtained following the use of NaH/1,4-dibromobutane, higher ,-dibromoalkanes, or -bromo--fluoroalkanes. Raising the reaction temperature opened the synthetic way toward O-6-guanine-alkylene-O-6-guanine and N1-guanine-alkylene-O-6-guanine symmetric and unsymmetric dimers. Protection of the substrate amine group to form N,N-dialkylformamidine provided the access to N1-guanine-alkylene-N1-guanine dimers.
ISSN:1042-7163
1098-1071
DOI:10.1002/hc.21399