squafosacin G | 1017587-50-6

• 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: squafosacin G
• 英文别名: (2S)-4-[(17S)-17-hydroxy-17-[(2S,5R)-5-[(1S)-1-hydroxyundecyl]oxolan-2-yl]heptadecyl]-2-methyl-2H-furan-5-one
• CAS: 1017587-50-6
• 化学式: C₃₇H₆₈O₅
• 分子量: 592.944
• InChiKey: GXSLYZATMZIZRT-WJYZGMOXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.9
• 重原子数：
  42
• 可旋转键数：
  28
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  76
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  squafosacin G 、 (R)-methoxytrifluoromethylphenylacetyl chloride 在 氘代吡啶 作用下， 反应 2.0h， 生成
  参考文献：
  名称：

  Mono-tetrahydrofuran Annonaceous Acetogenins from Annona squamosa as Cytotoxic Agents and Calcium Ion Chelators

  摘要：

  Eight new mono-tetrahydrofuran (THF)-type annonaceous acetogenins, squafosacins B, C, F, and G (1-4), squadiolins A-C (5-7), and cis-annotemoyin-1 (8), as well as eight known annonaceous acetogenins, glabranin, annotemoyins-1 and -2, bullatencin, cis-bullatencin, and uvariamicins-I, -II, and -III, were isolated from the seeds of Annona squamosa by HPLC. The structures of all new isolates were elucidated by using spectroscopic and chemical methods. Squadiolins A (5) and B (6) showed ng/mL potency against human Hep G2 hepatoma cells and significant cytotoxic activity against human MDA-MB-231 breast cancer cells. Squafosacin B (1) also exhibited significant cytotoxic activity against human Hep G2 and 313 hepatoma and MCF-7 breast cancer cells. In addition, the chelation of mono-THF acetogenins with calcium ions was investigated using isothermal titration calorimetry.

  DOI：

  10.1021/np0704957