28-azidosquamocin | 1094306-96-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 28-azidosquamocin
• CAS: 1094306-96-3
• 化学式: C₃₇H₆₅N₃O₆
• 分子量: 647.94
• InChiKey: JNFAANBEDRQCPH-PGDVHREDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.18
• 重原子数：
  46.0
• 可旋转键数：
  26.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  133.98
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  o-propargylfluorescein 、 28-azidosquamocin 在 copper(ll) sulfate pentahydrate 、 维生素 C 作用下， 以 水 、 叔丁醇 为溶剂， 反应 72.0h， 以55%的产率得到
  参考文献：
  名称：

  Highly cytotoxic and neurotoxic acetogenins of the Annonaceae: New putative biological targets of squamocin detected by activity-based protein profiling

  摘要：

  Acetogenins of the Annonaceae are strong inhibitors of mitochondrial complex I but discrepancies in the structure/activity relationships pled the search for other targets within the whole cell proteome. Combining hemisynthetic work, Cu-catalyzed Huisgen cycloaddition and proteomic techniques we have identified new putative protein targets of squamocin ruling out the previously accepted 'complex I dogma'. These results give new insights into the mechanism of action of these potent neurotoxic molecules. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.09.091
• 作为产物：
  描述：

  (5S)-3-[(13R)-13-[(2R,5R)-5-[(2R,5R)-5-[(1S,5S)-1,5-二羟基十一烷基]四氢呋喃-2-基]四氢呋喃-2-基]-13-羟基十三烷基]-5-甲基-5H-呋喃-2-酮 在 叠氮磷酸二苯酯 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以30%的产率得到28-azidosquamocin
  参考文献：
  名称：

  Highly cytotoxic and neurotoxic acetogenins of the Annonaceae: New putative biological targets of squamocin detected by activity-based protein profiling

  摘要：

  Acetogenins of the Annonaceae are strong inhibitors of mitochondrial complex I but discrepancies in the structure/activity relationships pled the search for other targets within the whole cell proteome. Combining hemisynthetic work, Cu-catalyzed Huisgen cycloaddition and proteomic techniques we have identified new putative protein targets of squamocin ruling out the previously accepted 'complex I dogma'. These results give new insights into the mechanism of action of these potent neurotoxic molecules. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.09.091