(S)-3-{(4R,13R)-4,13-Dihydroxy-13-[(2R,5R,2'R,5'R)-5'-((R)-1-hydroxy-undecyl)-octahydro-[2,2']bifuranyl-5-yl]-tridecyl}-5-methyl-5H-furan-2-one | 210230-74-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (S)-3-{(4R,13R)-4,13-Dihydroxy-13-[(2R,5R,2'R,5'R)-5'-((R)-1-hydroxy-undecyl)-octahydro-[2,2']bifuranyl-5-yl]-tridecyl}-5-methyl-5H-furan-2-one
• 英文别名: Bullacin B；(2S)-4-[(4R,13R)-4,13-dihydroxy-13-[(2R,5R)-5-[(2R,5R)-5-[(1R)-1-hydroxyundecyl]oxolan-2-yl]oxolan-2-yl]tridecyl]-2-methyl-2H-furan-5-one
• CAS: 210230-74-3
• 化学式: C₃₇H₆₆O₇
• 分子量: 622.927
• InChiKey: QUGFUBNTTOOGMC-UOCXRWNNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.3
• 重原子数：
  44
• 可旋转键数：
  25
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  105
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (R)-methoxytrifluoromethylphenylacetyl chloride 、 (S)-3-{(4R,13R)-4,13-Dihydroxy-13-[(2R,5R,2'R,5'R)-5'-((R)-1-hydroxy-undecyl)-octahydro-[2,2']bifuranyl-5-yl]-tridecyl}-5-methyl-5H-furan-2-one 在 4-二甲氨基吡啶 作用下， 以 吡啶 为溶剂， 反应 4.0h， 生成
  参考文献：
  名称：

  Three new bioactive bis-adjacent THF-ring acetogenins from the bark of Annona squamosa

  摘要：

  Continuing work on the bioactivity-directed fractionation of the bark of Annona squamosa has resulted in the discovery of three new Annonaceous acetogenins, (2,4-cis and tuans)-squamolinone (1), (2,4-cis and trans)-9-oxo-asimicinone (2), and bullacin B (3). Compounds 1-3 are all adjacent bis-THF ring acetogenins with 2 representing the first bis-ring acetogenin to contain a carbonyl along its aliphatic chain. Compound 3 was selectively cytotoxic in a panel of six human tumor cell lines with a potency of nearly a million times that of adriamycin against the MCF-7 (human breast adenocarcinoma) cell line. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(98)00018-2

文献信息

• Three new bioactive bis-adjacent THF-ring acetogenins from the bark of Annona squamosa
  作者：D Hopp

  DOI：10.1016/s0968-0896(98)00018-2

  日期：1998.5

  Continuing work on the bioactivity-directed fractionation of the bark of Annona squamosa has resulted in the discovery of three new Annonaceous acetogenins, (2,4-cis and tuans)-squamolinone (1), (2,4-cis and trans)-9-oxo-asimicinone (2), and bullacin B (3). Compounds 1-3 are all adjacent bis-THF ring acetogenins with 2 representing the first bis-ring acetogenin to contain a carbonyl along its aliphatic chain. Compound 3 was selectively cytotoxic in a panel of six human tumor cell lines with a potency of nearly a million times that of adriamycin against the MCF-7 (human breast adenocarcinoma) cell line. (C) 1998 Elsevier Science Ltd. All rights reserved.