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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| Published in | Heteroatom chemistry Vol. 28; no. 5 |
|---|---|
| Main Authors | , , , , |
| Format | Journal Article |
| Language | English |
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| Abstract | 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. |
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| AbstractList | 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,N2-(1,2-ethano)guanine, 1,N2-(1,3-propano)guanine, or 1,N2-(1,4-butano)guanine products, respectively. O6-Haloalkyl and N1-haloalkyl products were obtained following the use of NaH/1,4-dibromobutane, higher [alpha],[omega]-dibromoalkanes, or [alpha]-bromo-[omega]-fluoroalkanes. Raising the reaction temperature opened the synthetic way toward O6-guanine-alkylene-O6-guanine and N1-guanine-alkylene-O6-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. 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. |
| ArticleNumber | 21399 |
| Author | Golankiewicz, Bozenna Framski, Grzegorz Goslinski, Tomasz Januszczyk, Piotr Ostrowski, Tomasz |
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| Cites_doi | 10.1021/tx0500979 10.1039/c0ob00093k 10.1016/j.tetlet.2006.10.074 10.1016/j.bioorg.2007.10.004 10.1021/tx010181y 10.1021/tx9000489 10.1021/bi8008664 10.1021/tx015568f 10.1002/chem.201501103 10.1016/j.cbi.2014.12.003 10.1007/s00706-003-0592-1 10.1021/tx050141k 10.1016/j.bmc.2005.01.004 10.1021/tx0341355 10.1016/j.mrfmmm.2011.03.006 |
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| Keywords | 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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| Snippet | Reactions of 9-substituted guanine derivatives with NaH/1,2-dibromoethane, 1,3-dibromopropane, or 1,4-dibromobutane at room temperature resulted in the... |
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| Title | Alkylation of 9-substituted guanine derivatives with ,-dihaloalkanes |
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