[(8S,9R,10R,13R,14S,16R,17R)-17-[(E,2R)-6-acetyloxy-2-hydroxy-6-methyl-3-oxohept-4-en-2-yl]-16-hydroxy-4,4,9,13,14-pentamethyl-3,11-dioxo-8,10,12,15,16,17-hexahydro-7H-cyclopenta[a]phenanthren-2-yl] 6-[6-[5-[(3aS,4S,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]hexanoylamino]hexanoate | 1227476-35-8

• 分子结构分类: 有机化合物
• 英文名称: [(8S,9R,10R,13R,14S,16R,17R)-17-[(E,2R)-6-acetyloxy-2-hydroxy-6-methyl-3-oxohept-4-en-2-yl]-16-hydroxy-4,4,9,13,14-pentamethyl-3,11-dioxo-8,10,12,15,16,17-hexahydro-7H-cyclopenta[a]phenanthren-2-yl] 6-[6-[5-[(3aS,4S,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]hexanoylamino]hexanoate
• CAS: 1227476-35-8
• 化学式: C₅₄H₈₀N₄O₁₂S
• 分子量: 1009.31
• InChiKey: WRFUDOMOHMYLDH-VWODFBKZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  71
• 可旋转键数：
  25
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  269
• 氢给体数：
  6
• 氢受体数：
  13

反应信息

• 作为产物：
  描述：

  6-((6-((生物素基)氨基)己酰基)氨基)己酸 、 葫芦素 E 在 吡啶 、 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 反应 49.0h， 以45%的产率得到[(8S,9R,10R,13R,14S,16R,17R)-17-[(E,2R)-6-acetyloxy-2-hydroxy-6-methyl-3-oxohept-4-en-2-yl]-16-hydroxy-4,4,9,13,14-pentamethyl-3,11-dioxo-8,10,12,15,16,17-hexahydro-7H-cyclopenta[a]phenanthren-2-yl] 6-[6-[5-[(3aS,4S,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]hexanoylamino]hexanoate
  参考文献：
  名称：

  Cucurbitacin E as a new inhibitor of cofilin phosphorylation in human leukemia U937 cells

  摘要：

  Cucurbitane-type triterpenes, cucurbitacins B and E, were reported to exhibit cytotoxic effects in several cell lines mediated by JAK/STAT3 signaling. However, neither compound inhibited phosphorylation of STAT3 in human leukemia (U937) cells at low concentrations. We therefore synthesized a biotin-linked cucurbitacin E to isolate target proteins based on affinity for the molecule. As a result, cofilin, which regulates the depolymerization of actin, was isolated and suggested to be a target. Cucurbitacins E and I inhibited the phosphorylation of cofilin in a concentration-dependent manner, and their effective concentrations having the same range as the concentrations at which they had cytotoxic effects in U937 cells. In addition, the fibrous-/globular-actin ratio was decreased after treatment with cucurbitacin E in HT1080 cells. These findings suggested that the inhibition of cofilin's phosphorylation increased the severing activity of cofilin, and then the depolymerization of actin was enhanced after treatment with cucurbitacin E at lower concentrations. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.02.062