annullatin A | 1370709-00-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 香豆素
• 英文名称: annullatin A
• 英文别名: (2R)-2-(2-hydroxypropan-2-yl)-6-pentyl-2,3-dihydro-1-benzofuran-7-carbaldehyde
• CAS: 1370709-00-4
• 化学式: C₁₇H₂₄O₃
• 分子量: 276.376
• InChiKey: PWIFGZZYACPMJL-OAHLLOKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  annullatin B 在 戴斯-马丁氧化剂 作用下， 生成 annullatin A
  参考文献：
  名称：

  Dihydrobenzofurans as cannabinoid receptor ligands from Cordyceps annullata, an entomopathogenic fungus cultivated in the presence of an HDAC inhibitor

  摘要：

  The secondary metabolite production of Cordyceps annullata, an entomopathogenic fungus, was clearly enhanced by the addition of suberoyl bis-hydroxamic acid (SBHA), a histone deacetylase (HDAC) inhibitor, to the culture medium. Four new 2,3-dihydrobenzofurans, annullatins A-D (1-4), and a new aromatic polyketide, annullatin E (5) were isolated from the culture medium, and the structures, including the absolute stereochemistries, were determined by spectroscopic analysis, vibrational circular dichroism (VCD), and chemical transformations. Annullatin A (1) exhibited potent agonistic activity toward the cannabinoid receptors CB1 and CB2. Annullatin B (2) and D (4) displayed CB1 agonistic activity and CB2 inverse agonistic activity. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.02.088