(1E,4E)-1,5-bis(4-(allyloxy)-3-methoxyphenyl)penta-1,4-dien-3-one | 946161-24-6

• 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)-3-methoxyphenyl)penta-1,4-dien-3-one
• 英文别名: (1E,4E)-1,5-bis(3-methoxy-4-prop-2-enoxyphenyl)penta-1,4-dien-3-one
• CAS: 946161-24-6
• 化学式: C₂₅H₂₆O₅
• 分子量: 406.478
• InChiKey: CELDISYXCXJULG-MKICQXMISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  30
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (1E,4E)-1,5-bis(4-hydroxy-3-methoxyphenyl)penta-1,4-dien-3-one 、 3-溴丙烯 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 生成 (1E,4E)-1,5-bis(4-(allyloxy)-3-methoxyphenyl)penta-1,4-dien-3-one
  参考文献：
  名称：

  Synthesis and anti-inflammatory activities of mono-carbonyl analogues of curcumin

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2007.12.068

文献信息

• Chemoselective Synthesis and Anti-Kinetoplastidal Properties of 2,6-Diaryl-4H-tetrahydro-thiopyran-4-one S-Oxides: Their Interplay in a Cascade of Redox Reactions from Diarylideneacetones
  作者：Thibault Gendron、Don Antoine Lanfranchi、Nicole I. Wenzel、Hripsimée Kessedjian、Beate Jannack、Louis Maes、Sandrine Cojean、Thomas J. J. Müller、Philippe M. Loiseau、Elisabeth Davioud-Charvet

  DOI：10.3390/molecules29071620

  日期：——

  methodologies were developed and generalized from diarylideneacetones and 2,6-diaryl-4H-tetrahydro-thiopyran-4-ones to allow the introduction of a wide substitution profile and to prepare the related S-oxides. The in vitro biological activity and selectivity of diarylideneacetones, 2,6-diaryl-4H-tetrahydro-thiopyran-4-ones, and their S-sulfoxide and sulfone metabolites were evaluated against Trypanosoma

  2,6-二芳基-4H-四氢-噻喃-4-酮和相应的亚砜和砜衍生物被设计为通过前药作用降低其母体抗动铂二亚芳基丙酮的主要毒性。从二亚芳基丙酮和2,6-二芳基-4H-四氢-噻喃-4-酮中开发并推广了新的非对映选择性方法，以允许引入广泛的取代谱并制备相关的S-氧化物。评估了二亚芳基丙酮、2,6-二芳基-4H-四氢-噻喃-4-酮及其 S-亚砜和砜代谢物对布氏锥虫、克氏锥虫和各种利什曼原虫的体外生物活性和选择性。及其针对人成纤维细胞 hMRC-5 的细胞毒性。数据显示，迈克尔受体位点暂时被掩盖的硫化物、亚砜和砜对哺乳动物细胞的毒性较小，而对布氏锥虫、克氏锥虫、婴儿乳杆菌和锥虫的抗锥虫效力得以维持。 L. donovani，从而证实了前药策略的有效性。其作用机制被认为是由于二亚芳基丙酮参与涉及锥硫酮系统的级联氧化还原反应。迈克尔将二硫醇加成到双键上，形成伸长的聚合物，后者在 S-氧化后，随后进行顺式消除
• 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.
• 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.