1-(2,5-dimethylfuran-3-yl)-3-(2-hydroxyphenyl)prop-2-en-1-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: 1-(2,5-dimethylfuran-3-yl)-3-(2-hydroxyphenyl)prop-2-en-1-one
• 英文别名: 1-(2,5-Dimethylfuran-3-yl)-3-(2-hydroxyphenyl)prop-2-en-1-one
• 化学式: C₁₅H₁₄O₃
• 分子量: 242.274
• InChiKey: GFLAMCPDNPGHFB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  50.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,4-二羟基苯甲酸甲酯 、 1-(2,5-dimethylfuran-3-yl)-3-(2-hydroxyphenyl)prop-2-en-1-one 在 ethylenediamine Tetraacetic Acid 作用下， 以 甲苯 为溶剂， 反应 8.0h， 以84%的产率得到methyl 6-(2,5-dimethylfuran-3-yl)-1-hydroxy-12H-6,12-methanodibenzo[d,g][1,3]dioxocine-2-carboxylate
  参考文献：
  名称：

  催化剂控制的区域和立体选择性合成各种12 H -6,12-甲二苯并[ d，g ] [1,3]二氧杂环丁烷†

  摘要：

  我们描述了一种有效的一锅区域和立体选择性方法，用于合成各种1-羟基-12 H -6,12-甲氧基二苯并[ d，g ] [1,3]二氧杂环庚烷和3-羟基-12 H -6,12-甲烷二苯并[ d，g ] [1,3]二氧杂环辛酮使用乙二酸二铵二乙酸酯（EDDA）或对甲苯磺酸（PTSA）催化了各种间苯二酚与许多2-羟基查尔酮之间的反应。这些反应涉及催化剂控制的级联迈克尔型反应/双环化过程。重要的是，这些反应为生产通常在多步反应中制备的生物学上感兴趣的复杂分子提供了快速的合成途径。

  DOI：

  10.1039/c4ob00691g
• 作为产物：
  描述：

  3-乙酰基-2,5-二甲基呋喃 、 水杨醛 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 生成 1-(2,5-dimethylfuran-3-yl)-3-(2-hydroxyphenyl)prop-2-en-1-one
  参考文献：
  名称：

  Synthesis and Evaluation of Chalcone Derivatives as Inhibitors of Neutrophils' Chemotaxis, Phagocytosis and Production of Reactive Oxygen Species

  摘要：

  Inhibitory effects on neutrophils' chemotaxis, phagocytosis and production of reactive oxygen species (ROS) are among the important targets in developing anti‐inflammatory agents and immunosuppressants. Eight series of chalcone derivatives including five newly synthesized series were assessed for their inhibitory effects on chemotaxis, phagocytosis and ROS production in human polymorphonuclear neutrophils (PMNs). Inhibition of PMNs' chemotaxis and phagocytosis abilities were investigated using the Boyden chamber technique and the Phagotest kit, respectively, while ROS production was evaluated using luminol‐ and lucigenin‐based chemiluminescence assay. The new derivatives (4d and 8d), which contain 4‐methylaminoethanol functional group were active in all the assays performed. It was also observed that some of the compounds were active in inhibiting chemotaxis while others suppressed phagocytosis and ROS production. The information obtained gave new insight into chalcone derivatives with the potential to be developed as immunomodulators.

  DOI：

  10.1111/cbdd.12226

文献信息

• Synthesis and QSAR analysis of chalcone derivatives as nitric oxide inhibitory agent
  作者：Kok Wai Lam、Reaz Uddin、Choi Yi Liew、Chau Ling Tham、Daud A. Israf、Ahmad Syahida、Mohd. Basyaruddin Abdul Rahman、Zaheer Ul-Haq、Nordin H. Lajis

  DOI：10.1007/s00044-011-9706-1

  日期：2012.8

  In this study, thirty-eight chalcone analogs were synthesized and evaluated for nitric oxide (NO) inhibition activity on RAW 264.7 cells. Among these compounds, chalcones bearing furanyl group showed remarkable anti-inflammatory activity. Both compounds 2d and 2j were identified as the most potent NO inhibitor on IFN-gamma/LPS-activated RAW 264.7 cells. In order to examine the structure-activity relationship, a 3D QSAR analysis was carried out by comparative molecular field analysis (CoMFA) method on the selected chalcones. Partial least square analysis produced a statistically coherent model with good predictive value, r (2) = 0.989 and a good cross validated value, q (2) = 0.583.
• Synthesis and Evaluation of Chalcone Derivatives as Inhibitors of Neutrophils' Chemotaxis, Phagocytosis and Production of Reactive Oxygen Species
  作者：Syed N. A. Bukhari、Yasmin Tajuddin、Vannessa J. Benedict、Kok W. Lam、Ibrahim Jantan、Juriyati Jalil、Malina Jasamai

  DOI：10.1111/cbdd.12226

  日期：2014.2

  Inhibitory effects on neutrophils' chemotaxis, phagocytosis and production of reactive oxygen species (ROS) are among the important targets in developing anti‐inflammatory agents and immunosuppressants. Eight series of chalcone derivatives including five newly synthesized series were assessed for their inhibitory effects on chemotaxis, phagocytosis and ROS production in human polymorphonuclear neutrophils (PMNs). Inhibition of PMNs' chemotaxis and phagocytosis abilities were investigated using the Boyden chamber technique and the Phagotest kit, respectively, while ROS production was evaluated using luminol‐ and lucigenin‐based chemiluminescence assay. The new derivatives (4d and 8d), which contain 4‐methylaminoethanol functional group were active in all the assays performed. It was also observed that some of the compounds were active in inhibiting chemotaxis while others suppressed phagocytosis and ROS production. The information obtained gave new insight into chalcone derivatives with the potential to be developed as immunomodulators.
• Catalyst-controlled regio- and stereoselective synthesis of diverse 12H-6,12-methanodibenzo[d,g][1,3]dioxocines
  作者：Likai Xia、Hongyun Cai、Yong Rok Lee

  DOI：10.1039/c4ob00691g

  日期：——

  one-pot regio- and stereoselective method for synthesizing diverse 1-hydroxy-12H-6,12-methanodibenzo[d,g][1,3]dioxocines and 3-hydroxy-12H-6,12-methanodibenzo[d,g][1,3]dioxocines using ethylenediammonium diacetate (EDDA) or p-toluenesulfonic acid (PTSA) catalyzed reactions between various resorcinols and a number of 2-hydroxychalcones. These reactions involve a catalyst-controlled cascade Michael-type

  我们描述了一种有效的一锅区域和立体选择性方法，用于合成各种1-羟基-12 H -6,12-甲氧基二苯并[ d，g ] [1,3]二氧杂环庚烷和3-羟基-12 H -6,12-甲烷二苯并[ d，g ] [1,3]二氧杂环辛酮使用乙二酸二铵二乙酸酯（EDDA）或对甲苯磺酸（PTSA）催化了各种间苯二酚与许多2-羟基查尔酮之间的反应。这些反应涉及催化剂控制的级联迈克尔型反应/双环化过程。重要的是，这些反应为生产通常在多步反应中制备的生物学上感兴趣的复杂分子提供了快速的合成途径。