3-(2-hydroxyphenyl)-1-(5-methylfuran-2-yl)-prop-2-en-1-one | 292619-22-8

• 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: 3-(2-hydroxyphenyl)-1-(5-methylfuran-2-yl)-prop-2-en-1-one
• 英文别名: 3-(2-hydroxyphenyl)-1-(5-methylfuran-2-yl)propenone；3-(2-Hydroxyphenyl)-1-(5-methylfuran-2-yl)prop-2-en-1-one；3-(2-hydroxyphenyl)-1-(5-methylfuran-2-yl)prop-2-en-1-one
• CAS: 292619-22-8
• 化学式: C₁₄H₁₂O₃
• 分子量: 228.247
• InChiKey: YVHSHOIFTGABBG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 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：

  3-(2-hydroxyphenyl)-1-(5-methylfuran-2-yl)-prop-2-en-1-one 、 ((2-bromoallyl)sulfonyl)benzene 在 caesium carbonate 作用下， 以 乙腈 为溶剂， 反应 4.0h， 以61%的产率得到2-[2-methyl-3-(phenylsulfonyl)-4H-chromen-4-yl]-1-(5-methylfuran-2-yl)ethanone
  参考文献：
  名称：

  Facile synthesis of 4H-chromene derivatives via base-mediated annulation of ortho-hydroxychalcones and 2-bromoallyl sulfones

  摘要：

  硫醚烯磺酸2-溴丙烯基和邻羟基茜醌在铯碳酸盐催化下反应，产生了3-芳基磺酰基-4H-色烯衍生物，收率为58-67%（18个例子）。2-溴丙烯基磺酸酯在反应中作为芪烯磺酸酯的合成替代物。

  DOI：

  10.3762/bjoc.12.3
• 作为产物：
  描述：

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

  Facile synthesis of 4H-chromene derivatives via base-mediated annulation of ortho-hydroxychalcones and 2-bromoallyl sulfones

  摘要：

  硫醚烯磺酸2-溴丙烯基和邻羟基茜醌在铯碳酸盐催化下反应，产生了3-芳基磺酰基-4H-色烯衍生物，收率为58-67%（18个例子）。2-溴丙烯基磺酸酯在反应中作为芪烯磺酸酯的合成替代物。

  DOI：

  10.3762/bjoc.12.3

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.
• Effects of 3-(2-Hydroxyphenyl)-1-(5-methyl-furan-2-y-l) propenone (HMP) upon signalling pathways of lipopolysaccharide-induced iNOS synthesis in RAW 264.7 cells
  作者：Choi Yi Liew、Kok Wai Lam、Min Kyu Kim、Hanis H. Harith、Chau Ling Tham、Yoke Kqueen Cheah、Mohd Roslan Sulaiman、Nordin H. Lajis、Daud A. Israf

  DOI：10.1016/j.intimp.2010.10.011

  日期：2011.1

  We previously showed that 3-(2-hydroxyphenyl)-1-(5-methyl-furan-2-y-l)propenone (HMP), suppressed the synthesis of various proinflammatory mediators. In this study. HMP showed a dose-dependent inhibition of NO synthesis in the RAW 264.7 murine macrophage line. The inhibition of NO synthesis was related to inhibition of p38 phosphorylation and kinase activity that led to significant inhibition of phosphorylation of ATF-2. This effect in turn caused inhibition of AP-1-DNA binding which partially explains the inhibitory effect upon the synthesis of iNOS. HMP had no effect upon phosphorylation of JNK, ERK1/2 and STAT-1. Kinase activity of JNK and ERK1/2 was also not affected by HMP as determined by levels of phosphorylated c-jun and phosphorylated elk-1. Furthermore HMP failed to block phosphorylation of I kappa B alpha, and subsequent nuclear translocation and DNA-binding activity of p65 NF-kappa B in IFN-gamma/LPS-induced RAW 264.7 cells. Molecular docking experiments confirmed that HMP fits well in the highly conserved hydrophobic pocket of p38 MAP kinase. We conclude that the synthetic HMP is a chalcone analogue that selectively inhibits the p38/ATF-2 and AP-1 signaling pathways in the NO synthesis by the macrophage RAW 264.7. (C) 2010 Elsevier B.V. All rights reserved.
• Facile synthesis of 4<i>H</i>-chromene derivatives via base-mediated annulation of <i>ortho</i>-hydroxychalcones and 2-bromoallyl sulfones
  作者：Srinivas Thadkapally、Athira C Kunjachan、Rajeev S Menon

  DOI：10.3762/bjoc.12.3

  日期：——

  The cesium carbonate-mediated reaction of 2-bromoallyl sulfones and ortho-hydroxychalcones furnished 3-arylsulfonyl-4H-chromene derivatives in 58–67% yield (18 examples). 2-Bromoallyl sulfones functioned as synthetic surrogates for allenyl sulfones in the reaction.

  硫醚烯磺酸2-溴丙烯基和邻羟基茜醌在铯碳酸盐催化下反应，产生了3-芳基磺酰基-4H-色烯衍生物，收率为58-67%（18个例子）。2-溴丙烯基磺酸酯在反应中作为芪烯磺酸酯的合成替代物。