N-[6-(2-cyano-ethylsulfanyl)-9-(4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-9H-purin-2-yl]-2-phenoxy-acetamide | 138406-86-7

• 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: N-[6-(2-cyano-ethylsulfanyl)-9-(4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-9H-purin-2-yl]-2-phenoxy-acetamide
• CAS: 138406-86-7
• 化学式: C₂₁H₂₂N₆O₅S
• 分子量: 470.509
• InChiKey: XDHMASHMTQNYLZ-ZMSDIMECSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.49
• 重原子数：
  33.0
• 可旋转键数：
  9.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  155.41
• 氢给体数：
  3.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  N-[6-(2-cyano-ethylsulfanyl)-9-(4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-9H-purin-2-yl]-2-phenoxy-acetamide 在 N,N-二异丙基乙胺 作用下， 生成
  参考文献：
  名称：

  DESIGN OF HIGHLY EFFICIENT AND SELECTIVE TRANSFER REACTION OF NITROSYL GROUP TO dC AND d^MC RESULTING IN SPECIFIC DEAMINATION

  摘要：

  Nitric oxide (NO) is an important endogenous regulatory molecule, and S-nitrosothiols are believed to play a significant role in NO storage, transport, and delivery. Based on the ability to generate NO in vivo, S-nitrosothiols can be used as therapeutic drugs. In this study, we have developed an innovative method for sequence- and base-specific delivery of NO to a specific site of DNA followed by specific deamination.

  DOI：

  10.1081/ncn-200060312
• 作为产物：
  描述：

  9-((2R,4S,5R)-4-((tert-butyldimethylsilyl)oxy)-5-(((tert-butyldimethylsilyl)oxy)methyl)tetrahydrofuran-2-yl)-2-(2-phenoxyacetamido)-9H-purin-6-yl 2,4,6-triisopropylbenzenesulfonate 在 1-甲基吡咯烷 、 triethylamine tris(hydrogen fluoride) 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 18.5h， 生成 N-[6-(2-cyano-ethylsulfanyl)-9-(4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-9H-purin-2-yl]-2-phenoxy-acetamide
  参考文献：
  名称：

  Remarkable stabilization of antiparallel DNA triplexes by strong stacking effects of consecutively modified nucleobases containing thiocarbonyl groups

  摘要：

  The consecutive arrangement of 2'-deoxy-6-thioguanosines (s(6)Gs) and 4-thiothymidines (s(4)Ts) in antiparallel triplex-forming oligonucleotides (TFOs) considerably stabilized the resulting antiparallel triplexes with high base recognition ability by the strong stacking effects of thiocarbonyl groups. This result was remarkable because chemical modifications of the sugar moieties and nucleobases of antiparallel TFOs generally destabilize triplex structures. Moreover, in comparison with unmodified TFOs, it was found that TFOs containing s(6)Gs and s(4)Ts could selectively bind to the complementary DNA duplex but not to mismatched DNA duplexes or single-stranded RNA. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.11.079