Adenosine, 3'-azido-3'-deoxy-N-(1-naphthalenylmethyl)- | 676558-81-9

• 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: Adenosine, 3'-azido-3'-deoxy-N-(1-naphthalenylmethyl)-
• CAS: 676558-81-9
• 化学式: C₂₁H₂₀N₈O₃
• 分子量: 432.442
• InChiKey: KRRLGQLYMIMRCP-BZSOYRFXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.52
• 重原子数：
  32.0
• 可旋转键数：
  6.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  154.08
• 氢给体数：
  3.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  Adenosine, 3'-azido-3'-deoxy-N-(1-naphthalenylmethyl)- 在 indium 、 氯化铵 作用下， 以 乙醇 为溶剂， 反应 4.0h， 生成 3'-[4-(2,4-dichlorophenyloxy)butanamido]-3'-deoxy-N⁶-(1-naphthylmethyl)adenosine
  参考文献：
  名称：

  Antimalarial activity of N6-substituted adenosine derivatives. Part 3

  摘要：

  A series of novel 3'-amido-3'-deoxy-N-6-(l-naphthylmethyl)adenosines was synthesized applying a polymer-assisted solution phase (PASP) protocol and was tested for anti-malarial activity versus the Dd2 strain of Plasm odium falciparum. Further, this series and 62 adenosine derivatives were analyzed regarding 1-deoxy-D-xylulose 5-phospate (DOXP) reductoisomerase inhibition. Biological evaluations revealed that the investigated 3,N-6-disubstituted adenosine derivatives displayed moderate but significant activity against the P. falciparum parasite in the low-micromolar range. On the molecular level, DOXP reductoisomerase utilizing an adenosyl-containing substrate was identified as a promising metabolic target for ligands of adenosine binding motifs. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2003.11.008
• 作为产物：
  描述：

  2',5'-di-O-acetyl-3'-azido-3'-deoxyadenosine 在 甲醇 、 四氯化碳 、 氨 、 N,N-二异丙基乙胺 、 亚硝酸异戊酯 作用下， 以 丙醇 为溶剂， 反应 28.0h， 生成 Adenosine, 3'-azido-3'-deoxy-N-(1-naphthalenylmethyl)-
  参考文献：
  名称：

  Antimalarial activity of N6-substituted adenosine derivatives. Part 3

  摘要：

  A series of novel 3'-amido-3'-deoxy-N-6-(l-naphthylmethyl)adenosines was synthesized applying a polymer-assisted solution phase (PASP) protocol and was tested for anti-malarial activity versus the Dd2 strain of Plasm odium falciparum. Further, this series and 62 adenosine derivatives were analyzed regarding 1-deoxy-D-xylulose 5-phospate (DOXP) reductoisomerase inhibition. Biological evaluations revealed that the investigated 3,N-6-disubstituted adenosine derivatives displayed moderate but significant activity against the P. falciparum parasite in the low-micromolar range. On the molecular level, DOXP reductoisomerase utilizing an adenosyl-containing substrate was identified as a promising metabolic target for ligands of adenosine binding motifs. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2003.11.008