叠氮-三聚乙二醇-碘乙酰胺 | 1594986-04-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: 叠氮-三聚乙二醇-碘乙酰胺
• 英文名称: N-(2-(2-(2-(2-azidoethoxy)ethoxy)ethoxy)ethyl)-2-iodoacetamide
• 英文别名: Iodoacetamide-PEG3-azide；N-[2-[2-[2-(2-azidoethoxy)ethoxy]ethoxy]ethyl]-2-iodoacetamide
• CAS: 1594986-04-5
• 化学式: C₁₀H₁₉IN₄O₄
• 分子量: 386.19
• InChiKey: MVKSZBZLUGCWFA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  19
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  71.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N,N'-((14R,19R)-13,20-dioxo-1,32-bis(4-((5-((3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanamido)methyl)-1H-1,2,3-triazol-1-yl)-3,6,9,24,27,30-hexaoxa-16,17-dithia-12,21-diazadotriacontane-14,19-diyl)bis(4-benzoylbenzamide) 、 叠氮-三聚乙二醇-碘乙酰胺 在 三(2-羰基乙基)磷盐酸盐 、 碳酸氢钠 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以74%的产率得到N-((R)-1-azido-13,18-dioxo-30-(4-((5-((3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanamido)methyl)-1H-1,2,3-triazol-1-yl)-3,6,9,22,25,28-hexaoxa-15-thia-12,19-diazatriacontan-17-yl)-4-benzoylbenzamide
  参考文献：
  名称：

  Synthesis and evaluation of effective photoaffinity probe molecule of furospinosulin-1, a hypoxia-selective growth inhibitor

  摘要：

  The synthesis and evaluation of a photoaffinity probe molecule for furospinosulin-1, a hypoxia-selective growth inhibitor that we identified from marine sponge, was studied. An analogue carrying an alkyne tail showed potent hypoxia-selective inhibitory activity exceeding that of the parent molecule, and exhibited in vivo anti-tumor activity following oral administration. The alkyne moiety in the analogue was also found to be a good anchoring group for the preparation of probe molecules; a photoaffinity probe molecule having an optimized spacer length was selected through the systematic synthesis of several probes and the evaluation of their hypoxia-selective growth inhibitory activity and electrophoretic mobility shift properties. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.02.026
• 作为产物：
  描述：

  碘代乙酸酐 、 1-氨基-11-叠氮-3,6,9-三氧杂十一烷 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以83%的产率得到叠氮-三聚乙二醇-碘乙酰胺
  参考文献：
  名称：

  Synthesis and evaluation of effective photoaffinity probe molecule of furospinosulin-1, a hypoxia-selective growth inhibitor

  摘要：

  The synthesis and evaluation of a photoaffinity probe molecule for furospinosulin-1, a hypoxia-selective growth inhibitor that we identified from marine sponge, was studied. An analogue carrying an alkyne tail showed potent hypoxia-selective inhibitory activity exceeding that of the parent molecule, and exhibited in vivo anti-tumor activity following oral administration. The alkyne moiety in the analogue was also found to be a good anchoring group for the preparation of probe molecules; a photoaffinity probe molecule having an optimized spacer length was selected through the systematic synthesis of several probes and the evaluation of their hypoxia-selective growth inhibitory activity and electrophoretic mobility shift properties. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.02.026