(2E,8E,10E,14R)-1-O-acetyl-2,8,10-heptadecatrien-4,6-diyne-1,14-diol

• 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: (2E,8E,10E,14R)-1-O-acetyl-2,8,10-heptadecatrien-4,6-diyne-1,14-diol
• 英文别名: [(2E,8E,10E,14R)-14-hydroxyheptadeca-2,8,10-trien-4,6-diynyl] acetate
• 化学式: C₁₉H₂₄O₃
• 分子量: 300.398
• InChiKey: ZFJUNJXFNHXLTD-UZCJARIASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  22
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2E,8E,10E,14R)-1-O-acetyl-2,8,10-heptadecatrien-4,6-diyne-1,14-diol 在 lithium aluminium tetrahydride 作用下， 生成 水芹毒素
  参考文献：
  名称：

  Chemoenzymatic synthesis and cytotoxicity of oenanthotoxin and analogues

  摘要：

  We developed a synthetic scheme for the synthesis of naturally occurring (14R)-oenanthotoxin and several analogs. Key-steps of this synthesis were an efficient homo-coupling of alkynes and a chemoenzymatic resolution of racemic oenanthotoxin using novozyme 435 and vinyl acetate. The compounds were screened for their cytotoxic activity using a photometric sulforhodamine B assays and several human tumor cell lines. Oenanthotoxin and many derivatives thereof were cytotoxic to tumor cell lines as well as to non-malignant mouse fibroblasts. The highest activity was determined for human ovarian cancer cells A2780 with EC50 = 3.8 mu M. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.07.031
• 作为产物：
  描述：

  (E)-penta-2,4-dienal 在 吡啶 、 N-溴代丁二酰亚胺(NBS) 、 copper(l) iodide 、 lithium aluminium tetrahydride 、 正丁基锂 、 三溴化磷 、 N,N-二异丙基乙胺 、 lithium chloride 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 异丙醚 、 乙腈 为溶剂， 反应 31.67h， 生成 (2E,8E,10E,14R)-1-O-acetyl-2,8,10-heptadecatrien-4,6-diyne-1,14-diol 、 (2E,8E,10E,14S)-1,14-di-O-acetyl-2,8,10-heptadecatrien-4,6-diyne-1,14-diol
  参考文献：
  名称：

  Chemoenzymatic synthesis and cytotoxicity of oenanthotoxin and analogues

  摘要：

  We developed a synthetic scheme for the synthesis of naturally occurring (14R)-oenanthotoxin and several analogs. Key-steps of this synthesis were an efficient homo-coupling of alkynes and a chemoenzymatic resolution of racemic oenanthotoxin using novozyme 435 and vinyl acetate. The compounds were screened for their cytotoxic activity using a photometric sulforhodamine B assays and several human tumor cell lines. Oenanthotoxin and many derivatives thereof were cytotoxic to tumor cell lines as well as to non-malignant mouse fibroblasts. The highest activity was determined for human ovarian cancer cells A2780 with EC50 = 3.8 mu M. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.07.031

文献信息

• Chemoenzymatic synthesis and cytotoxicity of oenanthotoxin and analogues
  作者：Sven Sommerwerk、Lucie Heller、Bianka Siewert、René Csuk

  DOI：10.1016/j.bmc.2015.07.031

  日期：2015.9

  We developed a synthetic scheme for the synthesis of naturally occurring (14R)-oenanthotoxin and several analogs. Key-steps of this synthesis were an efficient homo-coupling of alkynes and a chemoenzymatic resolution of racemic oenanthotoxin using novozyme 435 and vinyl acetate. The compounds were screened for their cytotoxic activity using a photometric sulforhodamine B assays and several human tumor cell lines. Oenanthotoxin and many derivatives thereof were cytotoxic to tumor cell lines as well as to non-malignant mouse fibroblasts. The highest activity was determined for human ovarian cancer cells A2780 with EC50 = 3.8 mu M. (C) 2015 Elsevier Ltd. All rights reserved.