(1E,4E)-1,5-bis(4-hydroxy-3-methoxyphenyl)penta-1,4-dien-3-one | 131359-25-6

• 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(4-hydroxy-3-methoxyphenyl)penta-1,4-dien-3-one
• 英文别名: 1,5-bis(4-hydroxy-3-methoxyphenyl)-1,4-pentadiene-3-one；1,5-bis(4-hydroxy-3-methoxyphenyl)-1,4-pentadien-3-one；1,5-bis-(4-hydroxy-3-methoxyphenyl)penta-1,4-dien-3-one
• CAS: 131359-25-6
• 化学式: C₁₉H₁₈O₅
• 分子量: 326.349
• InChiKey: ISIMGBQRFXXNON-FCXRPNKRSA-N

物化性质

• 熔点：
  99-100 °C
• 沸点：
  536.4±50.0 °C(Predicted)
• 密度：
  1.266±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  76
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1E,4E)-1,5-bis(4-hydroxy-3-methoxyphenyl)penta-1,4-dien-3-one 以90%的产率得到sodium 4-[5-(4-hydroxy-3-methoxy-phenyI)-3-oxo-penta-1,4-dienyl]-2-methoxy-phenoIate
  参考文献：
  名称：

  WO2008/3155

  摘要：

  公开号：
• 作为产物：
  描述：

  sodium 4-[5-(4-hydroxy-3-methoxy-phenyI)-3-oxo-penta-1,4-dienyl]-2-methoxy-phenoIate 在 盐酸 作用下， 以 水 为溶剂， 以92%的产率得到(1E,4E)-1,5-bis(4-hydroxy-3-methoxyphenyl)penta-1,4-dien-3-one
  参考文献：
  名称：

  WO2008/3155

  摘要：

  公开号：

文献信息

• Synthesis and Anti-bacterial Properties of Mono-carbonyl Analogues of Curcumin
  作者：Guang Liang、Shulin Yang、Lijuan Jiang、Yu Zhao、Lili Shao、Jian Xiao、Faqing Ye、Yueru Li、Xiaokun Li

  DOI：10.1248/cpb.56.162

  日期：——

  The synthesis of three series of curcumin analogues with mono-carbonyl is described. Their in vitro anti-bacterial activities against seven Gram-positive and Gram-negative bacteria were tested and the effect of substituents on the aryl ring and the space structure of the linking strain were discussed. It was observed that part of the derivatives displayed significant activity when compared with curcumin and most of them exhibited activity against the ampicillin-resisted Enterobacter cloacae. Compounds A12, B09, B13, B14 and C09 show remarkable antibacterial activity in vitro. The result showed that heterocycle or long-chain substituents may enhance the activity of curcumin analogues.

  本文描述了三种单羰基姜黄素类似物的合成。对七种革兰氏阳性和革兰氏阴性细菌进行了体外抗菌活性测试，并讨论了取代基对芳环和连接张力的空间结构的影响。观察到，与姜黄素相比，部分衍生物显示出显著的活性，并且大多数衍生物对氨苄西林抵抗的阴沟肠杆菌表现出活性。化合物A12、B09、B13、B14和C09显示出显著的体外抗菌活性。结果显示，杂环或长链取代基可能增强姜黄素类似物的活性。
• Synthesis and Cytotoxic Evaluation of Monocarbonyl Analogs of Curcumin as Potential Anti‐Tumor Agents
  作者：Zheer Pan、Chengwei Chen、Yeli Zhou、Feng Xu、Yaozeng Xu

  DOI：10.1002/ddr.21291

  日期：2016.2

  Preclinical Research

  临床前研究
• BIS(ARYLMETHYLIDENE)ACETONE COMPOUND, ANTI-CANCER AGENT, CARCINOGENESIS-PREVENTIVE AGENT, INHIBITOR OF EXPRESSION OF Ki-Ras, ErbB2, c-Myc AND CYCLINE D1, BETA-CATENIN-DEGRADING AGENT, AND p53 EXPRESSION ENHANCER
  申请人：Shibata Hiroyuki

  公开号：US20100152493A1

  公开（公告）日：2010-06-17

  It has been demanded to improve the poor solubility of curcumin to develop an anti-tumor compound capable of inhibiting the growth of various cancer cells at a low concentration. Thus, disclosed is a novel synthetic compound, a bis(arylmethylidene)acetone, which has both of an excellent anti-tumor activity and a chemo-preventive activity. A bis(arylmethylidene)acetone (i.e., a derivative having a curcumin skeleton) which is an anti-tumor compound and has a chemo-preventive activity is synthesized and screened. A derivative having enhanced anti-tumor activity and chemo-preventive activity can be synthesized.

  要改善姜黄素的溶解度，以开发一种能够在低浓度下抑制各种癌细胞生长的抗肿瘤化合物。因此，披露了一种新型合成化合物，双(芳基甲基亚乙酮)，具有优异的抗肿瘤活性和化学预防活性。合成并筛选了一种双(芳基甲基亚乙酮)（即具有姜黄素骨架的衍生物），它是一种抗肿瘤化合物并具有化学预防活性。可以合成具有增强抗肿瘤活性和化学预防活性的衍生物。
• Synthesis and cytotoxic evaluation of monocarbonyl curcuminoids and their pyrazoline derivatives
  作者：Tim Van de Walle、Atiruj Theppawong、Charlotte Grootaert、Steven De Jonghe、Leentje Persoons、Dirk Daelemans、Kristof Van Hecke、John Van Camp、Matthias D’hooghe

  DOI：10.1007/s00706-019-02516-1

  日期：2019.12

  curcuminoids was prepared and screened for cytotoxic activity. In particular, bis-3-methoxy-4-hydroxy- and bis-4-methoxyphenyl-substituted monocarbonyls were synthesized and transformed into the corresponding three-dimensional N-acetylpyrazoline derivatives. In addition, a non-symmetrical indole-based monocarbonyl curcumin was prepared as well. Preliminary cytotoxic evaluation revealed significant effects for

  摘要制备了一小组结构上不同的单羰基姜黄素，并筛选了其细胞毒活性。特别地，合成了双-3-甲氧基-4-羟基-和双-4-甲氧基苯基取代的单羰基，并转化成相应的三维N-乙酰基吡唑啉衍生物。另外，还制备了非对称的基于吲哚的单羰基姜黄素。初步的细胞毒性评估显示了对4-羟基（吡唑啉）单羰基姜黄素的显着影响，而非酚类变体显示出相当差的活性。 图形摘要
• Anti-oxidant activities of curcumin and related enones
  作者：Waylon M. Weber、Lucy A. Hunsaker、Steve F. Abcouwer、Lorraine M. Deck、David L. Vander Jagt

  DOI：10.1016/j.bmc.2005.03.035

  日期：2005.6

  anti-oxidant properties. There are conflicting reports concerning the structural/electronic basis of the anti-oxidant activity of curcumin. Curcumin is a symmetrical diphenolic dienone. A series of enone analogues of curcumin were synthesized that included: (1) curcumin analogues that retained the 7-carbon spacer between the aryl rings; (2) curcumin analogues with a 5-carbon spacer; and (3) curcumin

  从香料姜黄获得的天然产物姜黄素（二氟甲酰甲烷，1,7-双（4-羟基-3-甲氧基苯基）-1,6-庚二烯-3,5-二酮）具有多种生物活性，包括抗癌，抗炎和抗血管生成活性。这些生物活性中的一些可能源自其抗氧化特性。关于姜黄素抗氧化活性的结构/电子基础的报道相互矛盾。姜黄素是对称的二酚二烯酮。合成了一系列姜黄素的烯酮类似物，包括：（1）保留在芳基环之间的7-碳间隔基的姜黄素类似物；（2）具有5碳间隔基的姜黄素类似物; （3）具有3个碳间隔基的姜黄素类似物（查耳酮）。这些系列包括保留或不包含酚基的成员。通过TRAP测定法和FRAP测定法测定抗氧化活性。大多数具有抗氧化活性的类似物保留了类似于姜黄素的酚环取代基。但是，许多没有酚取代基的类似物也是有活性的。这些非酚类类似物能够形成稳定的以碳为中心的叔基。