(1E,4E)-1,5-bis[3-methoxy-4-(tetrahydro-2H-pyran-2-yloxy)phenyl]penta-1,4-dien-3-one | 946161-22-4

• 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-(tetrahydro-2H-pyran-2-yloxy)phenyl]penta-1,4-dien-3-one
• 英文别名: (1E,4E)-2,5-bis(3-methoxy-4-(tetrahydro-2H-pyran-2-yloxy)phenyl)penta-1,4-dien-3-one；(1E,4E)-1,5-bis[3-methoxy-4-(oxan-2-yloxy)phenyl]penta-1,4-dien-3-one
• CAS: 946161-22-4
• 化学式: C₂₉H₃₄O₇
• 分子量: 494.585
• InChiKey: SXUDATWRYUURAA-UTLPMFLDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  36
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  72.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (1E,4E)-1,5-bis[3-methoxy-4-(tetrahydro-2H-pyran-2-yloxy)phenyl]penta-1,4-dien-3-one 在 甲醇 、 对甲苯磺酸 作用下， 反应 10.0h， 以85%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：

  Synthesis and Anti-bacterial Properties of Mono-carbonyl Analogues of Curcumin

  摘要：

  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。

  DOI：

  10.1248/cpb.56.162
• 作为产物：
  描述：

  3,4-二氢-2H-吡喃 在 4-甲基苯磺酸吡啶 、 sodium hydroxide 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 生成 (1E,4E)-1,5-bis[3-methoxy-4-(tetrahydro-2H-pyran-2-yloxy)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

• 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.
• Mono-carbonyl curcumin analogues as 11β-hydroxysteroid dehydrogenase 1 inhibitors
  作者：Han Lin、Guo-Xin Hu、Jingjing Guo、Yufei Ge、Guang Liang、Qing-Quan Lian、Yanhui Chu、Xiaohuan Yuan、Ping Huang、Ren-Shan Ge

  DOI：10.1016/j.bmcl.2013.05.080

  日期：2013.8

  A series of structurally novel mono-carbonyl curcumin analogues have been synthesized and biologically evaluated to test their inhibitory potencies and the structure-activity relationship (SAR) on human and rat 11 beta-hydroxysteroid dehydrogenase isoform (11 beta-HSD1) activities. 11 beta-HSD1 selective inhibitors have been discovered and compound A10 is discovered as a very potent with an IC50 value of 97 nM without inhibiting 11 beta-HSD2. (C) 2013 Elsevier Ltd. All rights reserved.