(7E,9E,15E)-17-hydroxy-7,9,15-heptadecatrien-11,13-diyn-4-one | 20311-75-5

• 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: (7E,9E,15E)-17-hydroxy-7,9,15-heptadecatrien-11,13-diyn-4-one
• 英文别名: 17-hydroxy-heptadeca-7t,9t,15t-triene-11,13-diyn-4-one；17-Hydroxy-heptadeca-7t,9t,15t-trien-11,13-diin-4-on；(7E,9E,15E)-17-hydroxyheptadeca-7,9,15-trien-11,13-diyn-4-one
• CAS: 20311-75-5
• 化学式: C₁₇H₂₀O₂
• 分子量: 256.345
• InChiKey: ORKCFSINEADMSV-JHTNEVNSSA-N

物化性质

• 熔点：
  53-56 °C
• 沸点：
  459.6±45.0 °C(Predicted)
• 密度：
  1.020±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (7E,9E,15E)-17-hydroxy-7,9,15-heptadecatrien-11,13-diyn-4-one 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 2.0h， 以82.6%的产率得到(2E,8E,10E)-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
• 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 、 水 、 三溴化磷 、 sodium hydride 、 N,N-二异丙基乙胺 、 lithium chloride 、 sodium hydroxide 作用下， 以 四氢呋喃 、 乙醚 、 水 、 乙腈 为溶剂， 反应 31.0h， 生成 (7E,9E,15E)-17-hydroxy-7,9,15-heptadecatrien-11,13-diyn-4-one 、 (7E,9E,15E,17E)-tetracosa-7,9,15,17-tetraen-11,13-diyne-4,21-dione
  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

• Bohlmann,F.; Rode,K.-M., Chemische Berichte, 1968, vol. 101, p. 1163 - 1175
  作者：Bohlmann,F.、Rode,K.-M.

  DOI：——

  日期：——
• Bohlmann; Viehe, Chemische Berichte, 1955, vol. 88, p. 1245,1251
  作者：Bohlmann、Viehe

  DOI：——

  日期：——
• 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.