5-iodo-4-N-methyl-2'-deoxycytidine | 85514-37-0

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 5-iodo-4-N-methyl-2'-deoxycytidine
• 英文别名: 1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-iodo-4-(methylamino)pyrimidin-2-one
• CAS: 85514-37-0
• 化学式: C₁₀H₁₄IN₃O₄
• 分子量: 367.143
• InChiKey: WBMAERUADWTBDO-XLPZGREQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  94.4
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-iodo-4-N-methyl-2'-deoxycytidine 、 1-Boc-吲哚-2-硼酸 在 palladium diacetate sodium carbonate 、 tppts 作用下， 以 乙腈 为溶剂， 反应 12.0h， 以70%的产率得到5-(indol-2-yl)-4-N-methyl-2'-deoxycytidine
  参考文献：
  名称：

  Fluorescent Pyrimidopyrimidoindole Nucleosides:  Control of Photophysical Characterizations by Substituent Effects

  摘要：

  10-(2-Deoxy-beta-D-ribofuranosyl)pyrimido[4',5':4,5]pyrimido[1,6-a]indole-6,9(7H)-dione (dC(PPI)) and its derivatives were synthesized via the Suzuki-Miyaura coupling reaction of 5-iododeoxycytidine with 5-substituted N-Boc-indole-2-borates and characterized by UV-vis and fluorescence spectroscopy. The new fluorescent nucleosides showed rather large Stokes shifts (116-139 nm) in an aqueous buffer. The fluorescent intensities were dependent on the nature of the substituents on the indole rings. The electron-withdrawing groups increased the fluorescent intensity while the electron-donating groups having lone pairs decreased it. Among the substituted dC(PPI) derivatives tested, the trimethylammonium derivative of dC(PPI) was found to emit the brightest fluorescent light. The solvatochromism of dC(PPI) and its derivatives was also studied. Some of the dC(PPI) derivatives showed interesting solvent-dependent fluorescence enhancement and could be useful as new fluorescent structural probes for nucleic acids. The Lippert-Mataga analyses of the Stokes shift were also carried out to obtain estimated values of the dipole moment of the excited states of some of the derivatives.

  DOI：

  10.1021/jo070206j
• 作为产物：
  描述：

  在 吡啶 、 ammonium hydroxide 作用下， 反应 12.0h， 以4.17 g的产率得到5-iodo-4-N-methyl-2'-deoxycytidine
  参考文献：
  名称：

  Fluorescent Pyrimidopyrimidoindole Nucleosides:  Control of Photophysical Characterizations by Substituent Effects

  摘要：

  10-(2-Deoxy-beta-D-ribofuranosyl)pyrimido[4',5':4,5]pyrimido[1,6-a]indole-6,9(7H)-dione (dC(PPI)) and its derivatives were synthesized via the Suzuki-Miyaura coupling reaction of 5-iododeoxycytidine with 5-substituted N-Boc-indole-2-borates and characterized by UV-vis and fluorescence spectroscopy. The new fluorescent nucleosides showed rather large Stokes shifts (116-139 nm) in an aqueous buffer. The fluorescent intensities were dependent on the nature of the substituents on the indole rings. The electron-withdrawing groups increased the fluorescent intensity while the electron-donating groups having lone pairs decreased it. Among the substituted dC(PPI) derivatives tested, the trimethylammonium derivative of dC(PPI) was found to emit the brightest fluorescent light. The solvatochromism of dC(PPI) and its derivatives was also studied. Some of the dC(PPI) derivatives showed interesting solvent-dependent fluorescence enhancement and could be useful as new fluorescent structural probes for nucleic acids. The Lippert-Mataga analyses of the Stokes shift were also carried out to obtain estimated values of the dipole moment of the excited states of some of the derivatives.

  DOI：

  10.1021/jo070206j