Cryptosphaerolide | 1228785-50-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并呋喃类
• 英文名称: Cryptosphaerolide
• 英文别名: [(1R,3S,4R,8S,10R,11S,14R)-4-hydroxy-10,11-dimethyl-7-methylidene-2,5-dioxatetracyclo[8.4.0.01,3.04,8]tetradecan-14-yl] 2-hydroxy-2-(hydroxymethyl)-4,6-dimethyloctanoate
• CAS: 1228785-50-9
• 化学式: C₂₆H₄₂O₇
• 分子量: 466.615
• InChiKey: MMGJJGNQFININV-OPYLLRRUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  33
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  109
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  甲醇 、 Cryptosphaerolide 在 Amberlite IR-120 H⁺ 作用下， 反应 72.0h， 以100%的产率得到[(1R,3S,4R,8S,10R,11S,14R)-4-methoxy-10,11-dimethyl-7-methylidene-2,5-dioxatetracyclo[8.4.0.01,3.04,8]tetradecan-14-yl] 2-hydroxy-2-(hydroxymethyl)-4,6-dimethyloctanoate
  参考文献：
  名称：

  Cryptosphaerolide, a Cytotoxic Mcl-1 Inhibitor from a Marine-Derived Ascomycete Related to the Genus Cryptosphaeria

  摘要：

  Examination of the saline fermentation products from the marine-derived ascomycete fungal strain CNL-523 (Cryptosphaeria sp.) resulted in the isolation of cryptosphaerolide (1). The new compound is an ester-substituted sesquiterpenoid related to the eremophilane class, The structure of the new compound was assigned by spectroscopic and chemical methods. Cryptosphaerolide was found to be an inhibitor of the protein Mcl-1, a cancer drug target involved in apoptosis. It also showed significant cytotoxicity against an HCT-116 human colon carcinoma cell line, indicating that the compound may be of value in exploring the Mcl-1 pathway as a target for cancer chemotherapy.

  DOI：

  10.1021/np1000889

文献信息

• Cryptosphaerolide, a Cytotoxic Mcl-1 Inhibitor from a Marine-Derived Ascomycete Related to the Genus <i>Cryptosphaeria</i>
  作者：Hyuncheol Oh、Paul R. Jensen、Brian T. Murphy、Catherine Fiorilla、John F. Sullivan、Timothy Ramsey、William Fenical

  DOI：10.1021/np1000889

  日期：2010.5.28

  Examination of the saline fermentation products from the marine-derived ascomycete fungal strain CNL-523 (Cryptosphaeria sp.) resulted in the isolation of cryptosphaerolide (1). The new compound is an ester-substituted sesquiterpenoid related to the eremophilane class, The structure of the new compound was assigned by spectroscopic and chemical methods. Cryptosphaerolide was found to be an inhibitor of the protein Mcl-1, a cancer drug target involved in apoptosis. It also showed significant cytotoxicity against an HCT-116 human colon carcinoma cell line, indicating that the compound may be of value in exploring the Mcl-1 pathway as a target for cancer chemotherapy.