(2S,5R,8R)-5-(1H-indol-3-ylmethyl)-2-methyl-8-phenyl-1,4,7,11-tetrazacyclononadecane-3,6,10,19-tetrone | 1045712-23-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酰胺类
• 英文名称: (2S,5R,8R)-5-(1H-indol-3-ylmethyl)-2-methyl-8-phenyl-1,4,7,11-tetrazacyclononadecane-3,6,10,19-tetrone
• CAS: 1045712-23-9
• 化学式: C₃₁H₃₉N₅O₄
• 分子量: 545.682
• InChiKey: QYIZNMBPMUCHKC-GCCWUPBUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  40
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  132
• 氢给体数：
  5
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  在 三异丙基硅烷 、 水 、 三氟乙酸 作用下， 反应 1.0h， 以6.9 mg的产率得到(2S,5R,8R)-5-(1H-indol-3-ylmethyl)-2-methyl-8-phenyl-1,4,7,11-tetrazacyclononadecane-3,6,10,19-tetrone
  参考文献：
  名称：

  Synthetic and pharmacological studies on new simplified analogues of the potent actin-targeting Jaspamide

  摘要：

  In the recent years, we focused our attention on the cyclodepsipeptide Jaspamide 1, an interesting marine metabolite, possessing a potent inhibitory activity against breast and prostate cancer, as a consequence of its ability to disrupt actin cytoskeleton dynamics. Although its biological pro. le has been well determined, many mechanistic details are still missing in terms of molecular target identification. For this reason, we decided to synthetically modify the natural metabolite, obtaining small arrays of unnatural variants useful to illuminate the structural requirements essential for the activity. Here, we report the synthesis of seven new Jaspamide analogues 2-8, containing, as the parent compound, a beta-amino acid in the cyclopeptide backbone. Their biological pro. le is also described. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.05.019