thespesilactam

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: thespesilactam
• 英文别名: 3,8-dihydroxy-7-methyl-5-propan-2-yl-1H-benzo[cd]indol-2-one
• 化学式: C₁₅H₁₅NO₃
• 分子量: 257.289
• InChiKey: CNWARQWFIXCVHX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  69.6
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  thespesilactam 、 三氟甲烷磺酸甲酯 以3 mg的产率得到3-O-methylthespesilactam
  参考文献：
  名称：

  3-O-methylthespesilactam, a new small-molecule anticancer pan-JAK inhibitor against A2058 human melanoma cells

  摘要：

  Natural product-inspired discovery of new drug leads plays a key role in drug development. Recently, small-molecule JAK inhibitors have been pursued for the development of anticancer therapeutics. However, most of these inhibitors reported up to now are multi-nitrogen polycyclic aromatic heterocycles. Undoubtedly, the discovery of new types of promising JAK-inhibitory leads is pivotal for JAK inhibitor-based anticancer drug development. Herein we report an unprecedented sesquiterpenoid-alkaloid named thespesilactam, containing a benzo[cd]indole scaffold, from the heartwood of the Portia tree, Thespesia populnea. Its 3-O-Me product, i.e. 8-hydroxy-5-isopropyl-3-methoxy-7-methylbenzo[cd]indol-2(1H)-one, named 3-O-methylthespesilactam, of which the structure was identified by NMR investigations and single-crystal X-ray diffraction analysis, was discovered as a new type of small-molecule anticancer pan-JAK inhibitor against A2058 human melanoma cells, and selective and potent inhibitor of JAK1 and TYK2. (C) 2013 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bcp.2013.08.065