3-Methoxy-5-<(Z)-heptadec-10'-enyl>phenol | 144078-13-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 3-Methoxy-5-<(Z)-heptadec-10'-enyl>phenol
• 英文别名: 3-<(Z)-10-heptadecenyl>5-methoxyphenol；(Z)-3-(heptadec-10-en-1-yl)-5-methoxyphenol；3-[(Z)-heptadec-10-enyl]-5-methoxyphenol
• CAS: 144078-13-7
• 化学式: C₂₄H₄₀O₂
• 分子量: 360.58
• InChiKey: AAKAGTMRUVKJKR-HJWRWDBZSA-N

物化性质

• 沸点：
  483.7±25.0 °C(Predicted)
• 密度：
  0.934±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.5
• 重原子数：
  26
• 可旋转键数：
  16
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-Methoxy-5-<(Z)-heptadec-10'-enyl>phenol 在 salcomine 、 氧气 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以42%的产率得到马蔺子素
  参考文献：
  名称：

  Identification of Novel ROS Inducers: Quinone Derivatives Tethered to Long Hydrocarbon Chains

  摘要：

  We performed the first synthesis of the 17-carbon chain-tethered quinone moiety 22 (SAN5201) of irisferin A, a natural product exhibiting anticancer activity, and its derivatives. We found that 22 is a potent ROS inducer and cytotoxic agent. Compound 25 (SAN7401), the hydroquinone form of 22, induced a significant release of intracellular ROS and apoptosis (EC50 = 1.3-2.6 mu M) in cancer cell lines, including A549 and HCT-116. Compared with the activity of a well-known ROS inducer, piperlongumine, 22 and 25 showed stronger cytotoxicity and higher selectivity over noncancerous cells. Another hydroquinone tethering 12-carbon chain, 26 (SAN4601), generated reduced levels of ROS but showed more potent cytotoxicity (EC50 = 0.8-1.6 mu M) in cancer cells, although it lacked selectivity over noncancerous cells, implying that the naturally occurring 17-carbon chain is also crucial for ROS production and a selective anticancer effect. Both 25 and 26 displayed strong, equipotent activities against vemurafenib-resistant SK-Mel2 melanoma cells and p53-deficient H1299 lung cancer cells as well, demonstrating their broad therapeutic potential as anticancer agents.

  DOI：

  10.1021/jm501846y
• 作为产物：
  描述：

  正庚基三苯基溴化磷 在 potassium tert-butylate 、 sodium hydride 、 乙硫醇 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成 3-Methoxy-5-<(Z)-heptadec-10'-enyl>phenol
  参考文献：
  名称：

  Identification of Novel ROS Inducers: Quinone Derivatives Tethered to Long Hydrocarbon Chains

  摘要：

  We performed the first synthesis of the 17-carbon chain-tethered quinone moiety 22 (SAN5201) of irisferin A, a natural product exhibiting anticancer activity, and its derivatives. We found that 22 is a potent ROS inducer and cytotoxic agent. Compound 25 (SAN7401), the hydroquinone form of 22, induced a significant release of intracellular ROS and apoptosis (EC50 = 1.3-2.6 mu M) in cancer cell lines, including A549 and HCT-116. Compared with the activity of a well-known ROS inducer, piperlongumine, 22 and 25 showed stronger cytotoxicity and higher selectivity over noncancerous cells. Another hydroquinone tethering 12-carbon chain, 26 (SAN4601), generated reduced levels of ROS but showed more potent cytotoxicity (EC50 = 0.8-1.6 mu M) in cancer cells, although it lacked selectivity over noncancerous cells, implying that the naturally occurring 17-carbon chain is also crucial for ROS production and a selective anticancer effect. Both 25 and 26 displayed strong, equipotent activities against vemurafenib-resistant SK-Mel2 melanoma cells and p53-deficient H1299 lung cancer cells as well, demonstrating their broad therapeutic potential as anticancer agents.

  DOI：

  10.1021/jm501846y

文献信息

• Phenols and a dioxotetrahydrodibenzofuran from seeds of Iris pallasii
  作者：Katsura Seki、Kazuo Haga、Ryohei Kaneko

  DOI：10.1016/0031-9422(94)00731-8

  日期：1995.3

  Abstract Three new compounds, along with four known ones, have been isolated from the seeds of Iris pallasii . On the basis of spectroscopic methods and chemical evidence, the new compounds were shown to be 2-[(Z)-10-heptadecenyl]-4,6-dimethoxyphenol, 3,5-dimethoxy-[(Z)-10-heptadecenyl]benzene and 9,9b-di[(Z)-10-heptadecenyl]-4a,8-dihydroxy-2,7-dimethoxy-1,4-dioxo-1,4,4a,9b-tetrahydrodibenzofuran.

  摘要 从鸢尾的种子中分离出三种新化合物以及四种已知化合物。根据光谱方法和化学证据，新化合物显示为 2-[(Z)-10-十七烯基]-4,6-二甲氧基苯酚、3,5-二甲氧基-[(Z)-10-十七烯基]苯和 9,9b-二[(Z)-10-十七烯基]-4a,8-二羟基-2,7-二甲氧基-1,4-二氧代-1,4,4a,9b-四氢二苯并呋喃。还讨论了这些化合物之间的生物遗传关系。
• Identification of Novel ROS Inducers: Quinone Derivatives Tethered to Long Hydrocarbon Chains
  作者：Yeonsun Hong、Sandip Sengupta、Wooyoung Hur、Taebo Sim

  DOI：10.1021/jm501846y

  日期：2015.5.14

  We performed the first synthesis of the 17-carbon chain-tethered quinone moiety 22 (SAN5201) of irisferin A, a natural product exhibiting anticancer activity, and its derivatives. We found that 22 is a potent ROS inducer and cytotoxic agent. Compound 25 (SAN7401), the hydroquinone form of 22, induced a significant release of intracellular ROS and apoptosis (EC50 = 1.3-2.6 mu M) in cancer cell lines, including A549 and HCT-116. Compared with the activity of a well-known ROS inducer, piperlongumine, 22 and 25 showed stronger cytotoxicity and higher selectivity over noncancerous cells. Another hydroquinone tethering 12-carbon chain, 26 (SAN4601), generated reduced levels of ROS but showed more potent cytotoxicity (EC50 = 0.8-1.6 mu M) in cancer cells, although it lacked selectivity over noncancerous cells, implying that the naturally occurring 17-carbon chain is also crucial for ROS production and a selective anticancer effect. Both 25 and 26 displayed strong, equipotent activities against vemurafenib-resistant SK-Mel2 melanoma cells and p53-deficient H1299 lung cancer cells as well, demonstrating their broad therapeutic potential as anticancer agents.