(1E,4E)-1,5-bis[4-(allyloxy)phenyl]penta-1,4-dien-3-one | 123203-31-6

• 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-(allyloxy)phenyl]penta-1,4-dien-3-one
• 英文别名: 1t,5t-bis-(4-allyloxy-phenyl)-penta-1,4-dien-3-one；1t,5t-Bis-(4-allyloxy-phenyl)-penta-1,4-dien-3-on；(1E,4E)-1,5-bis(4-prop-2-enoxyphenyl)penta-1,4-dien-3-one
• CAS: 123203-31-6
• 化学式: C₂₃H₂₂O₃
• 分子量: 346.426
• InChiKey: HMZANBKZFJOKDD-YDWXAUTNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  26
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 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：

  (1E,4E)-1,5-bis[4-(allyloxy)phenyl]penta-1,4-dien-3-one 、 苯肼 在 溶剂黄146 作用下， 生成
  参考文献：
  名称：

  Photophysical and charge transport properties of pyrazolines

  摘要：

  吡唑啉，一种在溶液和固态下均具有强烈绿色发射的分子，具有扩展的π-共轭，已经通过简单两步反应以高收率合成。

  DOI：

  10.1039/c5ra19520a
• 作为产物：
  描述：

  对羟基苯甲醛 在 氢氧化钾 、 sodium hydroxide 作用下， 生成 (1E,4E)-1,5-bis[4-(allyloxy)phenyl]penta-1,4-dien-3-one
  参考文献：
  名称：

  Toldy et al., Acta Chimica Academiae Scientiarum Hungaricae, 1954, vol. 4, p. 303,307

  摘要：

  DOI：

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。
• Exploration, synthesis and studies of gel forming simple sugar-chalcone derivatives
  作者：Arasappan Hemamalini、Thangamuthu Mohan Das

  DOI：10.1039/c4ra06544a

  日期：——

  Simple sugar-chalcone derivatives have been obtained by aldol condensation where aglycon–chalcone dimer was obtained as an unexpected product in addition to the sugar-chalcone

  简单糖-香豆素衍生物通过醛缩合成得，其中除了糖-香豆素外，还意外得到了缺苷-香豆素二聚体。
• Ungesättigte Imide und Benzaldehyd-Derivate enthaltende heisshärtbare Stoffgemische
  申请人：CIBA-GEIGY AG

  公开号：EP0302832A2

  公开（公告）日：1989-02-08

  Heisshärtbare Stoffgemische enthaltend (a) ein ungesättigtes lmid der Formel I und (b) ein Benzaldehyd-Derivat der Formel II worin zum Beispiel m = 2, n = Null, o = 1, R1, R2 und R3jeweils gleich Wasserstoff und R gleich 4,4'-Diphenylmethan sind, eignen sich für die Herstellung von Formkörpern mit ausgezeichneter Thermostabilität und Wärmealterungsbeständigkeit.

  一种热固性混合物，包含 (a) 式 I 的不饱和亚胺 和 (b) 式 II 的苯甲醛衍生物 例如，其中 m = 2，n = 0，o = 1，R1、R2 和 R3 均为氢，R 为 4,4'-二苯基甲烷。
• 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.
• Synthesis and anti-inflammatory activities of mono-carbonyl analogues of curcumin
  作者：Guang Liang、Xiaokun Li、Li Chen、Shulin Yang、Xudong Wu、Elaine Studer、Emily Gurley、Phillip B. Hylemon、Faqing Ye、Yueru Li、Huiping Zhou

  DOI：10.1016/j.bmcl.2007.12.068

  日期：2008.2

  Curcumin has been extensively studied for its anti-inflammatory activities. However, its potential beneficial effects on various disease preventions and treatments are limited by its unstable structure. The beta-diketone moiety renders curcumin to be rapidly metabolized by aldo -keto reductase in liver. In the present study, a series of curcumin analogues with more stable chemical structures were synthesized and several compounds showed an enhanced ability to inhibit lipopolysaccharide ( LPS)-induced TNF-alpha and IL-6 synthesis in macrophages. (C) 2007 Elsevier Ltd. All rights reserved.