angiopterlactone A | 1150247-69-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: angiopterlactone A
• 英文别名: (2S,3S)-3-[(2R,3R)-2-[(1S)-1-hydroxyethyl]-5-oxooxolan-3-yl]oxy-2-methyl-2,3-dihydropyran-6-one
• CAS: 1150247-69-0
• 化学式: C₁₂H₁₆O₆
• 分子量: 256.255
• InChiKey: BRMROXXXIVEVKO-DADSOTLSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  82.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  angiopterlactone A 、 (R)-methoxytrifluoromethylphenylacetyl chloride 在 吡啶 、 4-二甲氨基吡啶 作用下， 以70%的产率得到[(1S)-1-[(2R,3R)-3-[[(2S,3S)-2-methyl-6-oxo-2,3-dihydropyran-3-yl]oxy]-5-oxooxolan-2-yl]ethyl] (2S)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoate
  参考文献：
  名称：

  Lactones from Angiopteris caudatiformis

  摘要：

  Angiopterlactones A (1) and B (2), two unique lactones, and three known lactones, osmundalactone (3), osmundalin (4), and 3,5-dihydroxy-gamma-caprolactone (5), have been isolated from the rhizome of Angiopteris caudatiformis. The structures of I and 2 were determined by NMR and MS methods, and the structure of 2 was confirmed by X-ray crystallography. The absolute configurations of I and 2 were assigned by application of the CD excitation chirality method and the modified Mosher's method. Compound 1 was slightly cytotoxic against HeLa cells, with an IC50 value of 68.8 mu M, and compounds 3 and 4 showed moderate insect antifeeding activity against Plutella xylostella and Heliothis virescens.

  DOI：

  10.1021/np900027m