(E,E)-3,5-bis(3,4-dimethoxystyryl)isoxazole | 1118765-46-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: (E,E)-3,5-bis(3,4-dimethoxystyryl)isoxazole
• 英文别名: 3,5-bis(3,4-dimethoxystyryl)isoxazole；3,5-bis[(E)-2-(3,4-dimethoxyphenyl)ethenyl]-1,2-oxazole
• CAS: 1118765-46-0
• 化学式: C₂₃H₂₃NO₅
• 分子量: 393.439
• InChiKey: LOLJOYNPAHAQMV-NXZHAISVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  63
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  二甲氧基姜黄素 在 盐酸羟胺 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 40.0h， 以90%的产率得到(E,E)-3,5-bis(3,4-dimethoxystyryl)isoxazole
  参考文献：
  名称：

  Synthesis and evaluation of electron-rich curcumin analogues

  摘要：

  The natural product curcumin has long been recognized for its medicinal properties and is utilized for the treatment of many diseases. However, it remains unknown whether this activity is based on its presumably promiscuous scaffold, or if it results from the Michael acceptor properties of the alpha,beta-unsaturated 1,3-diketone moiety central to its structure. To probe this issue, electron-rich pyrazole and isoxazole analogues were prepared and evaluated against two breast cancer cell lines, which resulted in the identification of several compounds that exhibit low micromolar to mid nanomolar anti-proliferative activity. A conjugate addition study was also performed to compare the relative electrophilicity of the diketone, pyrazole and isoxazole analogues. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.10.057

文献信息

• Isoxazole analogs of curcuminoids with highly potent multidrug-resistant antimycobacterial activity
  作者：Chatchawan Changtam、Poonpilas Hongmanee、Apichart Suksamrarn

  DOI：10.1016/j.ejmech.2010.07.003

  日期：2010.10

  bisdemethoxycurcumin (3), the curcuminoid constituents of the medicinal plant Curcuma longa L., have been structurally modified to 55 analogs and antimycobacterial activity against Mycobacterium tuberculosis has been evaluated. Among the highly active curcuminoids, the isoxazole analogs are the most active group, with mono-O-methylcurcumin isoxazole (53) being the most active compound (MIC 0.09 μg/mL). It was

  姜黄素（1），去甲氧基姜黄素（2）和双去甲氧基姜黄素（3）（药用植物姜黄的姜黄素成分）已在结构上修饰为55个类似物，并已评估了其对结核分枝杆菌的抗分枝杆菌活性。在高活性姜黄素类化合物中，异恶唑类似物是活性最高的基团，单-O-甲基姜黄素异恶唑（53）是活性最高的化合物（MIC 0.09μg/ mL）。它的活性比母体化合物姜黄素（1）高1131倍，分别比标准药物卡那霉素和异烟肼高18倍和2倍。化合物53还显示出对耐多药结核分枝杆菌临床分离株的高活性，MIC值为0.195–3.125μg/ mL。姜黄素类似物表现出抗分枝杆菌活性的结构要求是在异戊基环上存在一个异恶唑环和两个不饱和键。紧密连接于异恶唑环的氮官能团的芳环上合适的对烷氧基的存在和另一个芳环上的游离对羟基的存在增强了生物活性。
• Curcuminoid-derived 3,5-bis(styryl)isoxazoles - Mechanochemical synthesis and antioxidant activity
  作者：DAISY R SHERIN、KALLIKAT N RAJASEKHARAN

  DOI：10.1007/s12039-016-1119-8

  日期：2016.8

  Mechanochemical synthesis of curcuminoid-derived 3,5-bis(styryl)isoxazoles and their antioxidant activities are reported. Mechanochemical synthesis of curcuminoid-derived 3,5-bis(styryl)isoxazoles (4a-g) and their antioxidant activities are reported.

  姜黄素衍生的3,5-双（苯乙烯基）异恶唑的机械化学合成及其抗氧化活性已有报道。 姜黄素衍生的3,5-双（苯乙烯基）异恶唑（4a-g）的机械化学合成及其抗氧化活性已有报道。
• Synthesis and evaluation of electron-rich curcumin analogues
  作者：Michael W. Amolins、Laura B. Peterson、Brian S.J. Blagg

  DOI：10.1016/j.bmc.2008.10.057

  日期：2009.1

  The natural product curcumin has long been recognized for its medicinal properties and is utilized for the treatment of many diseases. However, it remains unknown whether this activity is based on its presumably promiscuous scaffold, or if it results from the Michael acceptor properties of the alpha,beta-unsaturated 1,3-diketone moiety central to its structure. To probe this issue, electron-rich pyrazole and isoxazole analogues were prepared and evaluated against two breast cancer cell lines, which resulted in the identification of several compounds that exhibit low micromolar to mid nanomolar anti-proliferative activity. A conjugate addition study was also performed to compare the relative electrophilicity of the diketone, pyrazole and isoxazole analogues. (C) 2008 Elsevier Ltd. All rights reserved.