O⁶-benzyl-N²,3-ethenoguanine | 62962-39-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: O⁶-benzyl-N²,3-ethenoguanine
• 英文别名: 4-benzyloxy-1(3)H-imidazo[2,1-b]purine；O⁶-Benzyl-N²,3-aethenoguanin；benzyl 3H-imidazo[2,1-b]purin-4-yl ether；4-phenylmethoxy-3H-imidazo[2,1-b]purine
• CAS: 62962-39-4
• 化学式: C₁₄H₁₁N₅O
• 分子量: 265.274
• InChiKey: OFTLUQKGEPXSAK-UHFFFAOYSA-N

物化性质

• 密度：
  1.47±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  68.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  O⁶-benzyl-N²,3-ethenoguanine 在 盐酸 作用下， 反应 4.0h， 生成 3,5-二氢咪唑并[2,1-b]嘌呤-4-酮
  参考文献：
  名称：

  4,5-Epoxy-2(E)-decenal-Induced Formation of 1,N⁶-Etheno-2‘-deoxyadenosine and 1,N²-Etheno-2‘-deoxyguanosine Adducts

  摘要：

  trans-4,5-Epoxy-2(E)-decenal reacted with 2'-deoxyadenosine to give 1,N-6-etheno-2'-deoxyadenosine as well as other 2'-deoxyadenosine adducts. It also reacted with 2'-deoxyguanosine to give 1,N-2-etheno-2'-deoxyguanosine and other 2'-deoxyguanosine adducts. Synthetic trans-4,5-epoxy-2(E)-decenal was quite stable under the reaction conditions that were used. It was not contaminated with 2,3-epoxyoctanal, a potential precursor to the formation of unsubstituted etheno adducts. Furthermore, using a sensitive LC/MS assay, it was possible to show that no 2,3-epoxyoctanal was formed during prolonged incubations of trans-4,5-epoxy-2(E)-decenal. Therefore, trans-4,5-epoxy-2(E)-decenal, a primary product of lipid peroxidation, is a precursor to the formation of 1,1,N-6-etheno-2'-deoxyadenosine and 1,N-2-etheno-2'-deoxyguanosine. There is no need for an additional oxidation step such as would be required if trans,trans-2,4-decadienal or 4-hydroxy-2-nonenal were the lipid hydroperoxide decomposition products that initiated the formation of unsubstituted etheno adducts. These findings provide an important link between a primary product of lipid peroxidation and a mutagenic DNA lesion that has been detected in human tissues.

  DOI：

  10.1021/tx010147j
• 作为产物：
  描述：

  氯乙醛 、 O-6-苄基鸟嘌呤 以 乙醇 为溶剂， 反应 120.0h， 以80%的产率得到O⁶-benzyl-N²,3-ethenoguanine
  参考文献：
  名称：

  4,5-Epoxy-2(E)-decenal-Induced Formation of 1,N⁶-Etheno-2‘-deoxyadenosine and 1,N²-Etheno-2‘-deoxyguanosine Adducts

  摘要：

  trans-4,5-Epoxy-2(E)-decenal reacted with 2'-deoxyadenosine to give 1,N-6-etheno-2'-deoxyadenosine as well as other 2'-deoxyadenosine adducts. It also reacted with 2'-deoxyguanosine to give 1,N-2-etheno-2'-deoxyguanosine and other 2'-deoxyguanosine adducts. Synthetic trans-4,5-epoxy-2(E)-decenal was quite stable under the reaction conditions that were used. It was not contaminated with 2,3-epoxyoctanal, a potential precursor to the formation of unsubstituted etheno adducts. Furthermore, using a sensitive LC/MS assay, it was possible to show that no 2,3-epoxyoctanal was formed during prolonged incubations of trans-4,5-epoxy-2(E)-decenal. Therefore, trans-4,5-epoxy-2(E)-decenal, a primary product of lipid peroxidation, is a precursor to the formation of 1,1,N-6-etheno-2'-deoxyadenosine and 1,N-2-etheno-2'-deoxyguanosine. There is no need for an additional oxidation step such as would be required if trans,trans-2,4-decadienal or 4-hydroxy-2-nonenal were the lipid hydroperoxide decomposition products that initiated the formation of unsubstituted etheno adducts. These findings provide an important link between a primary product of lipid peroxidation and a mutagenic DNA lesion that has been detected in human tissues.

  DOI：

  10.1021/tx010147j

文献信息

• 4,5-Epoxy-2(<i>E</i>)-decenal-Induced Formation of 1,<i>N</i>⁶-Etheno-2‘-deoxyadenosine and 1,<i>N</i>²-Etheno-2‘-deoxyguanosine Adducts
  作者：Seon Hwa Lee、Tomoyuki Oe、Ian A. Blair

  DOI：10.1021/tx010147j

  日期：2002.3.1

  trans-4,5-Epoxy-2(E)-decenal reacted with 2'-deoxyadenosine to give 1,N-6-etheno-2'-deoxyadenosine as well as other 2'-deoxyadenosine adducts. It also reacted with 2'-deoxyguanosine to give 1,N-2-etheno-2'-deoxyguanosine and other 2'-deoxyguanosine adducts. Synthetic trans-4,5-epoxy-2(E)-decenal was quite stable under the reaction conditions that were used. It was not contaminated with 2,3-epoxyoctanal, a potential precursor to the formation of unsubstituted etheno adducts. Furthermore, using a sensitive LC/MS assay, it was possible to show that no 2,3-epoxyoctanal was formed during prolonged incubations of trans-4,5-epoxy-2(E)-decenal. Therefore, trans-4,5-epoxy-2(E)-decenal, a primary product of lipid peroxidation, is a precursor to the formation of 1,1,N-6-etheno-2'-deoxyadenosine and 1,N-2-etheno-2'-deoxyguanosine. There is no need for an additional oxidation step such as would be required if trans,trans-2,4-decadienal or 4-hydroxy-2-nonenal were the lipid hydroperoxide decomposition products that initiated the formation of unsubstituted etheno adducts. These findings provide an important link between a primary product of lipid peroxidation and a mutagenic DNA lesion that has been detected in human tissues.