5-{[bis-(3-aminopropyl)amino]acetamido-1-propynyl}adenosine | 959153-79-8

• 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: 5-{[bis-(3-aminopropyl)amino]acetamido-1-propynyl}adenosine
• 英文别名: N-[3-[6-amino-9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]purin-2-yl]prop-2-ynyl]-2-[bis(3-aminopropyl)amino]acetamide
• CAS: 959153-79-8
• 化学式: C₂₁H₃₃N₉O₅
• 分子量: 491.55
• InChiKey: OWWNIXYLPIEGQW-RAXVHSSMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.6
• 重原子数：
  35
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  224
• 氢给体数：
  7
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  2-[bis(3-aminopropyl)amino]-N-prop-2-ynylacetamide 、 2-碘腺苷 在 四(三苯基膦)钯 copper(l) iodide 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以19%的产率得到5-{[bis-(3-aminopropyl)amino]acetamido-1-propynyl}adenosine
  参考文献：
  名称：

  Construction of polyamine-modified uridine and adenosine derivatives—evaluation of DNA binding capacity and cytotoxicity in vitro

  摘要：

  We here report the synthesis of the two polyamine-based nucleoside derivatives 5-{[bis-(3-aminopropyl)amino]acetamido-1-propynyl} uridine and 2-{[bis-(3-aminopropyl)amino]-acetamido-1-propynyl}adenosine. The various polyamine derivatives have been used in thermal melting analysis using DNA from herring testes, and in cellular studies using four different cell lines. The compounds were all found to be non-toxic, thus holding good promise for future use as siRNA building blocks. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.07.030

文献信息

• Construction of polyamine-modified uridine and adenosine derivatives—evaluation of DNA binding capacity and cytotoxicity in vitro
  作者：Johannes Ghatnekar、Margareta Hägerlöf、Stina Oredsson、Kersti Alm、Sofi K.C. Elmroth、Tina Persson

  DOI：10.1016/j.bmc.2007.07.030

  日期：2007.12

  We here report the synthesis of the two polyamine-based nucleoside derivatives 5-[bis-(3-aminopropyl)amino]acetamido-1-propynyl} uridine and 2-[bis-(3-aminopropyl)amino]-acetamido-1-propynyl}adenosine. The various polyamine derivatives have been used in thermal melting analysis using DNA from herring testes, and in cellular studies using four different cell lines. The compounds were all found to be non-toxic, thus holding good promise for future use as siRNA building blocks. (C) 2007 Elsevier Ltd. All rights reserved.