(1E,4E)-1,5-bis(3-methoxy-4-((3-methylbut-2-en-1-yl)oxy)phenyl)penta-1,4-dien-3-one

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (1E,4E)-1,5-bis(3-methoxy-4-((3-methylbut-2-en-1-yl)oxy)phenyl)penta-1,4-dien-3-one
• 英文别名: (1E,4E)-1,5-bis{3-methoxy-4-[(3-methylbut-2-en-1-yl)oxy]phenyl}penta-1,4-dien-3-one；1,5-bis[3-methoxy-4-(3-methyl-but-2-enyloxy)-phenyl]penta-1,4-dien-3-one；(1E,4E)-1,5-bis[3-methoxy-4-(3-methylbut-2-enoxy)phenyl]penta-1,4-dien-3-one
• 化学式: C₂₉H₃₄O₅
• 分子量: 462.586
• InChiKey: FSSATMWVXDXRTJ-MKICQXMISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  34
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1E,4E)-1,5-bis(3-methoxy-4-((3-methylbut-2-en-1-yl)oxy)phenyl)penta-1,4-dien-3-one 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 生成 3,5-bis-[3-methoxy-4-(3-methyl-but-2-enyloxy)-phenyl]-4-nitro-cyclohexanone
  参考文献：
  名称：

  WO2008/3155

  摘要：

  公开号：
• 作为产物：
  描述：

  (1E,4E)-1,5-bis[3-methoxy-4-(tetrahydro-2H-pyran-2-yloxy)phenyl]penta-1,4-dien-3-one 在 盐酸 、 potassium carbonate 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 生成 (1E,4E)-1,5-bis(3-methoxy-4-((3-methylbut-2-en-1-yl)oxy)phenyl)penta-1,4-dien-3-one
  参考文献：
  名称：

  姜黄素单羰基类似物作为潜在抗肿瘤剂的合成及细胞毒性评价。

  摘要：

  临床前研究

  DOI：

  10.1002/ddr.21291

文献信息

• New method for the preparation of 1,5-bis(4-hydroxy-3-metoxy-phenyl)-penta-1,4-dien-3-one and derivatives with antitumoral properties
  申请人：Suarez Agustin Quincoces Jose

  公开号：US20060128997A1

  公开（公告）日：2006-06-15

  This patent of invention reports the method for the preparation of 1,5-bis(4-hydroxy-3-methoxyphenyl)-penta-1,4-dien-3-one and derivatives with antitumoral properties: the sample denominated 37 compound was obtained with high yield and purity with ultrasonic technique presenting cytostatic activity (growth inhibition) in the concentrations evaluated and cytotoxic activity (cellular death) from the concentration of 0.25 mg/mL against nine different types of human cancer cell lines. This compound has a LD50, equals to 8.54 g/Kg. That means this product can be considered itself as practically nontoxic. Doxorubicin, anticarcinogen medicine used as reference in all these tests, is a product extremely toxic (LD50 of 20 mg/Kg) and it does not inhibit the growth of Mama NCI-ADR cell line (the one that expresses the phenotype of resistance against multiple drugs), therefore our product presented a strong cytostatic activity. Other derivatives also presented a strong cytostatic activity, specially the one denominated EHB1 compound.

  本发明专利介绍了具有抗肿瘤特性的 1,5-双（4-羟基-3-甲氧基苯基）-1,4-戊二烯-3-酮及其衍生物的制备方法：通过超声波技术获得的 37 号化合物样品产量高、纯度高，在评估浓度下具有细胞抑制活性（生长抑制），在 0.25 毫克/毫升浓度下对九种不同类型的人类癌细胞株具有细胞毒性活性（细胞死亡）。该化合物的半数致死剂量为 8.54 克/千克。这意味着该产品本身实际上是无毒的。在所有这些测试中用作参考的抗癌药物多柔比星是一种毒性极强的产品（半数致死剂量为 20 毫克/千克），它不能抑制 Mama NCI-ADR 细胞系（表达对多种药物耐药表型的细胞系）的生长，因此我们的产品具有很强的细胞抑制活性。其他衍生物也具有很强的细胞抑制活性，特别是名为 EHB1 的化合物。
• Synthesis and biological evaluation of allylated and prenylated mono-carbonyl analogs of curcumin as anti-inflammatory agents
  作者：Zhiguo Liu、Longguang Tang、Peng Zou、Yali Zhang、Zhe Wang、Qilu Fang、Lili Jiang、Gaozhi Chen、Zheng Xu、Huajie Zhang、Guang Liang

  DOI：10.1016/j.ejmech.2013.10.061

  日期：2014.3

  Curcumin has been shown to possess anti-inflammatory activities but has been limited for its low stability and poor bioavailability. We have previously reported four series of 5-carbon linker-containing mono-carbonyl analogs of curcumin (MACs). In continuation of our ongoing research, we designed and synthesized 33 novel allylated or prenylated MACs here, and evaluated their anti-inflammatory effects in RAW 264.7 macrophages. A majority of them effectively inhibited the LPS-induced expression of TNF-alpha and IL-6, especially IL-6. The preliminary SAR and quantitative SAR analysis were conducted. Compound 14q is the most potent analog among them, and exhibits significant protection against LPS-induced death in septic mice. Together, these data present a series of new analogs of curcumin as promising anti-inflammatory agents. (C) 2013 Elsevier Masson SAS. All rights reserved.
• NEW METHOD FOR THE PREPARATION OF 1,5-BIS(4-HYDROXY-3-METOXY-PHENYL)-PENTA-1,4-DIEN-3-ONE AND DERIVATIVES WITH ANTITUMORAL PROPERTIES
  申请人：Fundacio de Amparo Pesquisa do Estado des Sao Paulo

  公开号：EP1572614A2

  公开（公告）日：2005-09-14
• METHOD FOR THE PREPARATION OF 1,5-BIS(4-HYDROXY-3-METOXY-PHENYL)-PENTA-1,4-DIEN-3-ONE
  申请人：Fundação de Amparo à Pesquisa do Estado de São Paulo

  公开号：EP1572614B1

  公开（公告）日：2013-12-25
• METHODS TO PREPARE PENTA-1,4-DIEN-3-ONES AND SUBSTITUTED CYCLOHEXANONES AND DERIVATIVES WITH ANTITUMORAL AND ANTIPARASITIC PROPERTIES, THE COMPOUNDS AND THEIR USES
  申请人：Uniban - Universidade Bandeirante De São Paulo

  公开号：EP2054365A2

  公开（公告）日：2009-05-06