N-isobutyroyl-5’-carboxy-2’,3’-di-O-(carbobenzyloxy)guanosine | 1453185-65-3

• 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-isobutyroyl-5’-carboxy-2’,3’-di-O-(carbobenzyloxy)guanosine
• CAS: 1453185-65-3
• 化学式: C₃₀H₂₉N₅O₁₁
• 分子量: 635.587
• InChiKey: GYKYYZGNQUWIMQ-IMIIHFCZSA-N

物化性质

• 密度：
  1.52±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.14
• 重原子数：
  46.0
• 可旋转键数：
  10.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  210.26
• 氢给体数：
  3.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  N-isobutyroyl-5’-carboxy-2’,3’-di-O-(carbobenzyloxy)guanosine 在 吡啶 、 palladium 10% on activated carbon 、 氢气 、 2-乙氧基-1-乙氧碳酰基-1,2-二氢喹啉 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 15.67h， 生成 N-isobutyroyl-5’-N-Boc-L-Lys(OMe)-2’,3’-di-O-(palmitoyl)guanosine
  参考文献：
  名称：

  Synthesis, DNA binding and anti-leukemic activity of an aminoacyl nucleolipid

  摘要：

  The synthesis and characterization of a new class of DNA binding molecule exhibiting potent and selective anti-leukemic activity is described. The synthesis of an aminoacyl nucleolipid was developed from an efficient EEDQ coupling strategy, in which a series of seven bioconjugates were synthesized in yields of 53-78%. Guanosine bioconjugate 7, was used as building block for the synthesis of a target aminoacyl nucleolipid 14. Its GRP78 DNA binding affinity was confirmed by gel shift assay, CD spectroscopy, T-m measurements and dynamic light scattering experiments. Moreover, in a single dose (10 mu M) screen against a panel of 60 cancer cell lines, aminoacyl nucleolipid 14 was found to selectively trigger greater than 90% cell death in a SR human leukemia cancer cell line. The reported aminoacyl nucleolipid represents a useful model for a new class of DNA binding molecules for the development of potent and selective anti-cancer agents. Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2013.07.030
• 作为产物：
  描述：

  N-isobutyroyl-2’,3’-di-O-(carbobenzyloxy)guanosine 在 2,2,6,6-四甲基哌啶氧化物 、 碘苯二乙酸 作用下， 以 乙醚 、 水 、 丙酮 、 乙腈 为溶剂， 以82%的产率得到N-isobutyroyl-5’-carboxy-2’,3’-di-O-(carbobenzyloxy)guanosine
  参考文献：
  名称：

  Synthesis, DNA binding and anti-leukemic activity of an aminoacyl nucleolipid

  摘要：

  The synthesis and characterization of a new class of DNA binding molecule exhibiting potent and selective anti-leukemic activity is described. The synthesis of an aminoacyl nucleolipid was developed from an efficient EEDQ coupling strategy, in which a series of seven bioconjugates were synthesized in yields of 53-78%. Guanosine bioconjugate 7, was used as building block for the synthesis of a target aminoacyl nucleolipid 14. Its GRP78 DNA binding affinity was confirmed by gel shift assay, CD spectroscopy, T-m measurements and dynamic light scattering experiments. Moreover, in a single dose (10 mu M) screen against a panel of 60 cancer cell lines, aminoacyl nucleolipid 14 was found to selectively trigger greater than 90% cell death in a SR human leukemia cancer cell line. The reported aminoacyl nucleolipid represents a useful model for a new class of DNA binding molecules for the development of potent and selective anti-cancer agents. Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2013.07.030