Alkylation of 9-substituted guanine derivatives with ,-dihaloalkanes

被引：0

作者：

Framski, Grzegorz ^{[1
]}

Goslinski, Tomasz ^{[2
]}

Januszczyk, Piotr ^{[1
]}

Golankiewicz, Bozenna ^{[1
]}

Ostrowski, Tomasz ^{[1
]}

机构：

[1] Polish Acad Sci, Inst Bioorgan Chem, Poznan, Poland

[2] Poznan Univ Med Sci, Dept Chem Technol Drugs, Poznan, Poland

来源：

HETEROATOM CHEMISTRY | 2017年 / 28卷 / 05期

关键词：

-dihaloalkanes; N1-guanine substitution; nucleoside dimers; O6-guanine substitution; tricyclic guanine; SITE-SPECIFIC SYNTHESIS; 1; N2-PROPANODEOXYGUANOSINE ADDUCTS; PHYSIOLOGICAL CONDITIONS; CHEMICAL CARCINOGENESIS; ANTIVIRAL ACTIVITY; DNA-ADDUCTS; CROSS-LINK; ACYCLOVIR; ACROLEIN; 2'-DEOXYGUANOSINE;

D O I：

10.1002/hc.21399

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

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.

引用

页数：13

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