10-(3,5-dimethoxyphenyl)decanal | 137786-97-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 10-(3,5-dimethoxyphenyl)decanal
• CAS: 137786-97-1
• 化学式: C₁₈H₂₈O₃
• 分子量: 292.419
• InChiKey: DPXPJWKXRMCJML-UHFFFAOYSA-N

物化性质

• 沸点：
  414.6±25.0 °C(Predicted)
• 密度：
  0.975±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于乙酸乙酯

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  21
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  10-(3,5-dimethoxyphenyl)decanal 在 salcomine 、 potassium tert-butylate 、 氧气 、 sodium hydride 、 乙硫醇 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 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：

  1,9-壬二醇 在 光气 、 正丁基锂 、 palladium 10% on activated carbon 、 氢气 、 silica gel 、 sodium hydride 、 二甲基亚砜 、 三乙胺 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 7.0h， 生成 10-(3,5-dimethoxyphenyl)decanal
  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

• Naturally Occurring 5-Lipoxygenase Inhibitor. II. Structures and Syntheses of Ardisianones A and B, and Maesanin, Alkenyl-1,4-benzoquinones from the Rhizome of Ardisia japonica.
  作者：Yoshiyasu FUKUYAMA、Yuuko KIRIYAMA、Junko OKINO、Mitsuaki KODAMA、Hideyuki IWAKI、Sigeki HOSOZAWA、Kuniaki MATSUI

  DOI：10.1248/cpb.41.561

  日期：——

  New alkenyl-1,4-benzoquinones, ardisianones A (1) and B (2), and the known maesanin (3) as 5-lipoxygenase inhibitors have been isolated from the rhizome of Ardisia japonica. Their structures have been elucidated as 2-methoxy-6-[(Z)-10'-pentadecenyl]-1,4-benzoquinone and 5-hydroxy-2-methoxy-6-[(Z)-8'-tridecenyl]-1,4-benzoquinone, respectively, on the basis of spectroscopic data and chemical degradation

  新的烯基-1,4-苯醌，ardisianones A（1）和B（2），以及作为5-脂氧合酶抑制剂的已知的maesanin（3）已从Ardisia japonica的根茎中分离出来。已阐明它们的结构为2-甲氧基-6-[（（Z）-10'-十五碳烯基] -1,4-苯醌和5-羟基-2-甲氧基-6-[（Z）-8'-十三碳烯基]- 1,4-苯醌分别基于光谱数据和化学降解。Ardisianone A（1），maesanin（3）和belamcandol A（7）是从belamcandol B（6）合成的，很容易通过9-（2-四氢吡喃氧基）壬醛与3,5-二甲氧基苄基三苯基ph溴化物的Wittig反应制备，然后用硫代乙醇钠选择性脱甲基。
• Structures of Belamcandols A and B Isolated from the Seed of Belamcanda chinensis.
  作者：Yoshiyasu FUKUYAMA、Junko OKINO、Mitsuaki KODAMA

  DOI：10.1248/cpb.39.1877

  日期：——

  The structuers of belamcandols A (1) and B (2) isolated from the seeds of Belamcanda chinensis have beenassigned to 2, 4-dimethyoxy-6-((Z)-10'-pentadecenyl)phenol and 1-O-methyl-5-((Z)-10'-pentadecenyl)resorcinol, respectively, based on spectroscopic data and chemical degradation. Belamcandol A inhibits 5-ilpoxygenase activity at IC50 0.60 μM.

  根据光谱数据和化学降解结果，从白桦脂种子中分离出的白桦脂醇 A（1）和 B（2）的结构物分别被定为 2，4-二甲氧基-6-((Z)-10'-十五烯基)苯酚和 1-O-甲基-5-((Z)-10'-十五烯基)间苯二酚。Belamcandol A 抑制 5-ilpoxygenase 活性的 IC50 值为 0.60 μM。