N⁶-[(1H-benzotriazol-1-yl)(pyren-1-yl)methy]-2'-deoxyadenosine | 292862-89-6

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: N⁶-[(1H-benzotriazol-1-yl)(pyren-1-yl)methy]-2'-deoxyadenosine
• 英文别名: (2R,3S,5R)-5-[6-[[benzotriazol-1-yl(pyren-1-yl)methyl]amino]purin-9-yl]-2-(hydroxymethyl)oxolan-3-ol
• CAS: 292862-89-6
• 化学式: C₃₃H₂₆N₈O₃
• 分子量: 582.621
• InChiKey: CFTJOTQAKDCJEE-QFJMYPLRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  44
• 可旋转键数：
  6
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  136
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  N⁶-[(1H-benzotriazol-1-yl)(pyren-1-yl)methy]-2'-deoxyadenosine 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以70%的产率得到(-)-N⁶-(1-pyrenylmethyl)-2'-deoxyadenosine
  参考文献：
  名称：

  1H-苯并三唑作为合成辅助剂在 N6-(芳甲基)-2'-脱氧腺苷的简便途径中：插入三向连接的 DNA 嵌入剂

  摘要：

  The 2'-deoxy-N-6-(naphthalen-1-ylmethyl)-(5a) and N-6-(pyren-1-ylntethyl)adenosine (5b) were synthesized in two steps from 2'-deoxyadenosine and the adequate arenecarbaldehyde with 1H-benzotriazole as a synthetic auxiliary (Scheme). When the N-6-(arylmethyl)-2'-deoxyadenosines were inserted into the junction region of a DNA three-way junction, its thermal stability increased.

  DOI：

  10.1002/1522-2675(20000705)83:7<1408::aid-hlca1408>3.0.co;2-u
• 作为产物：
  描述：

  T406石油添加剂 、 1-芘甲醛 、 2'-脱氧腺苷 在 溶剂黄146 作用下， 以 甲苯 为溶剂， 反应 6.0h， 以80%的产率得到N⁶-[(1H-benzotriazol-1-yl)(pyren-1-yl)methy]-2'-deoxyadenosine
  参考文献：
  名称：

  1H-苯并三唑作为合成辅助剂在 N6-(芳甲基)-2'-脱氧腺苷的简便途径中：插入三向连接的 DNA 嵌入剂

  摘要：

  The 2'-deoxy-N-6-(naphthalen-1-ylmethyl)-(5a) and N-6-(pyren-1-ylntethyl)adenosine (5b) were synthesized in two steps from 2'-deoxyadenosine and the adequate arenecarbaldehyde with 1H-benzotriazole as a synthetic auxiliary (Scheme). When the N-6-(arylmethyl)-2'-deoxyadenosines were inserted into the junction region of a DNA three-way junction, its thermal stability increased.

  DOI：

  10.1002/1522-2675(20000705)83:7<1408::aid-hlca1408>3.0.co;2-u

文献信息

• 1H-Benzotriazole as Synthetic Auxiliary in a Facile Route to N6-(Arylmethyl)-2′-deoxyadenosines: DNA Intercalators Inserted into Three-Way Junctions
  作者：Sherif A. El-Kafrawy、Magdy A. Zahran、Erik B. Pedersen、Claus Nielsen

  DOI：10.1002/1522-2675(20000705)83:7<1408::aid-hlca1408>3.0.co;2-u

  日期：2000.7.5

  The 2'-deoxy-N-6-(naphthalen-1-ylmethyl)-(5a) and N-6-(pyren-1-ylntethyl)adenosine (5b) were synthesized in two steps from 2'-deoxyadenosine and the adequate arenecarbaldehyde with 1H-benzotriazole as a synthetic auxiliary (Scheme). When the N-6-(arylmethyl)-2'-deoxyadenosines were inserted into the junction region of a DNA three-way junction, its thermal stability increased.