10-(2-deoxy-β-D-ribofuranosyl)pyrimido[4',5':4,5]pyrimido[1,6-a]indole-6,9(7H)-dione | 945493-54-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 10-(2-deoxy-β-D-ribofuranosyl)pyrimido[4',5':4,5]pyrimido[1,6-a]indole-6,9(7H)-dione
• 英文别名: 4-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-4,6,8,10-tetrazatetracyclo[8.7.0.02,7.011,16]heptadeca-1(17),2,6,11,13,15-hexaene-5,9-dione
• CAS: 945493-54-9
• 化学式: C₁₈H₁₆N₄O₅
• 分子量: 368.349
• InChiKey: KEIIWOAHGYECJE-RRFJBIMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  27
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  116
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  10-(2-deoxy-β-D-ribofuranosyl)pyrimido[4',5':4,5]pyrimido[1,6-a]indole-6,9(7H)-dione 、 4,4'-双甲氧基三苯甲基氯 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以73%的产率得到10-[2-deoxy-5-O-(4,4'-dimethoxytrityl)-β-D-ribofuranosyl]pyrimido[4',5':4,5]pyrimido[1,6-a]indole-6,9(7H)-dione
  参考文献：
  名称：

  通过堆叠相互作用稳定的稳定 DNA 三链体的新核苷酸对

  摘要：

  开发了适用于 DNA 三链体形成的新核苷酸对。我们设计了包含 5-芳基脱氧胞苷衍生物 (dC5Ars) 和环状脱氧胞苷衍生物 dCPPP 和 dCPPI 的寡核苷酸，它们具有扩大的芳族区域，作为第二条链。作为配对伙伴，选择了两种类型的无碱基残基（C3​​：丙烯接头，phi：无碱基碱基）。结论是，当 5-芳基修饰的胞嘧啶碱基以空间拟合的方式与 TFO 中的无碱基位点配对时，所得三链体的稳定性显着增加。C3 对 dC5Ars 的识别是有选择性的，因为它们的芳香部分和无碱基位点侧翼的核碱基之间存在堆积相互作用。这些结果表明新的核苷酸三联体在 DNA 三联体形成中的潜在效用，

  DOI：

  10.1021/ja800991m
• 作为产物：
  描述：

  1-Boc-吲哚 在 palladium diacetate 硼酸三异丙酯 、 sodium carbonate 、 tppts 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 水 、 乙腈 为溶剂， 反应 14.0h， 生成 10-(2-deoxy-β-D-ribofuranosyl)pyrimido[4',5':4,5]pyrimido[1,6-a]indole-6,9(7H)-dione
  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

文献信息

• A Pyrimidopyrimidoindole Nucleoside (dC^<i>PPI</i>): Photophysical Properties and Thermal Stability of the Modified Dna Duplexes
  作者：Masahiro Mizuta、Kohji Seio、Kenichi Miyata、Akihiro Ohkubo、Haruhiko Taguchi、Mitsuo Sekine

  DOI：10.1080/15257770701533164

  日期：2007.11.26

  A new fluorescent deoxycytidine analog, 10-(2-deoxy-beta-D-,ribofuranosyl)-pyrimido[1,5:4,5]pyrimido[l, 6-a]indole-6,9(7H)-dione (dC(PPI)) was synthesized. Its fluorescent properties were studied in detail. It was found that this fluorescent nucleoside dC(PPI) could be used as a fluorescent label for DNA probes with minimal disturbance of their overall structure.