1-(2-hydroxy-phenyl)-5-(4-methoxy-phenyl)-penta-1,4-dien-3-one | 119607-54-4

• 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: 1-(2-hydroxy-phenyl)-5-(4-methoxy-phenyl)-penta-1,4-dien-3-one
• 英文别名: 1-(2-Hydroxy-phenyl)-5-(4-methoxy-phenyl)-penta-1,4-dien-3-on；(1E,4E)-1-(2-hydroxyphenyl)-5-(4-methoxyphenyl)penta-1,4-dien-3-one
• CAS: 119607-54-4
• 化学式: C₁₈H₁₆O₃
• 分子量: 280.323
• InChiKey: FKEUPOLZGNBWPO-BBYAVRKXSA-N

物化性质

• 熔点：
  139 °C
• 沸点：
  492.9±40.0 °C(Predicted)
• 密度：
  1.191±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(2-hydroxy-phenyl)-5-(4-methoxy-phenyl)-penta-1,4-dien-3-one 在 盐酸 、 高氯酸 作用下， 以57%的产率得到2-(4-methoxy-styryl)-chromenylium; perchlorate
  参考文献：
  名称：

  Makin, S. M.; Markina, T. A.; Boiko, I. I., Journal of Organic Chemistry USSR (English Translation), 1988, vol. 24, # 11, p. 2182 - 2187

  摘要：

  DOI：
• 作为产物：
  描述：

  水杨醛 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 生成 1-(2-hydroxy-phenyl)-5-(4-methoxy-phenyl)-penta-1,4-dien-3-one
  参考文献：
  名称：

  新型3-（（（2-（（1 E，4 E）-3-Oxo-5-arylpenta-1,4-dien-1-yl）phenoxy）methyl）-4（3 H）-的合成及抗病毒活性喹唑啉酮衍生物

  摘要：

  一系列新颖的3-（（2-（（1 E，4 E）-3-氧代-5-芳基戊-1,4-二烯-1-基）苯氧基）甲基）-4（3 H）-喹唑啉酮衍生物被设计和合成。抗病毒生物测定法表明，与市售药物宁南霉素相比，一些化合物在体内对烟草花叶病毒（TMV）表现出更高的抗病毒活性。特别地，化合物A 5，A 12，A 25和A 27在体内对TMV具有可观的治愈性生物活性，50％有效浓度范围为132.25至156.10μg/ mL。这些值优于宁南霉素（281.22μg/ mL）的值，表明新颖的4（3 H含有1,4-戊二烯-3-一个部分的）-喹唑啉酮衍生物可以有效地控制TMV。在野外研究中评估抗病毒特性以及这些衍生物增强的抗病毒活性的潜在机制是未来研究的有趣话题。

  DOI：

  10.1021/jf502162y

文献信息

• Novel Phosphorylated Penta-1,4-dien-3-one Derivatives: Design, Synthesis, and Biological Activity
  作者：Lijuan Chen、Tao Guo、Rongjiao Xia、Xu Tang、Ying Chen、Cheng Zhang、Wei Xue

  DOI：10.3390/molecules24050925

  日期：——

  A series of novel phosphorylated penta-1,4-dien-3-one derivatives were designed and synthesized. The structures of all title compounds were determined by 1H-NMR, 13C-NMR, 31P-NMR, and high-resolution mass spectrometry (HRMS). Bioassay results showed that several of the title compounds exhibited remarkable antibacterial and antiviral activities. Among these, compound 3g exhibited substantial antibacterial

  设计并合成了一系列新型磷酸化penta-1,4-dien-3-one 衍生物。所有标题化合物的结构均通过 1H-NMR、13C-NMR、31P-NMR 和高分辨率质谱 (HRMS) 测定。生物测定结果表明，几种标题化合物表现出显着的抗菌和抗病毒活性。其中，化合物 3g 对黄单胞菌 pv 表现出显着的抗菌活性。稻瘟病菌 (Xoo) 的 50% 有效浓度 (EC50) 值为 8.6 μg/mL，显着优于双甲噻唑 (BT) (58.8 μg/mL) 和硫代二唑铜 (TC) (78.7 μg/mL)。此外，化合物3h对烟草花叶病毒（TMV）表现出显着的保护活性，EC50值为104.2 μg/mL，优于宁南霉素（386.2 μg/mL）。此外，还研究了关于化合物 3h 和 3j 与 TMV 外壳蛋白 (TMV CP) 相互作用的微型热泳和分子对接实验。化合物3h和3j以0.028和0.23 μmol/L的解离常数与TMV
• Design, synthesis, and antiviral activity of novel rutin derivatives containing 1, 4-pentadien-3-one moiety
  作者：Yu Han、Yan Ding、Dandan Xie、Deyu Hu、Pei Li、Xiangyang Li、Wei Xue、Linhong Jin、Baoan Song

  DOI：10.1016/j.ejmech.2015.01.017

  日期：2015.3

  Rutin (compound 5) and some compounds (compounds 1-4 and 6) were isolated from Artemisia princeps Pamp (A. prirtceps Pamp.) and a series of novel rutin derivatives containing 1,4-pentadien-3-one moiety were designed and synthesized. The target compounds were characterized by proton nuclear magnetic resonance spectroscopy (H-1 NMR), carbon nuclear magnetic resonance spectroscopy (C-13 NMR), and ESI-MS. Bioassay results indicated that some of the compounds showed good to excellent antiviral activities against tobacco mosaic virus (TMV) and cucumber mosaic virus (CMV) at 500 mu g/mL in vivo. The 50% effective concentrations (EC50) of the compound 7r against CMV was 394.78 mu g/mL, which was better than that of Ningnanmycin (432.22 mu g/mL). These results indicated that novel rutin derivatives containing 1,4-pentadien-3-one moiety can effectively control CMV. (C) 2015 Elsevier Masson SAS. All rights reserved.
• Antiviral activity and interaction mechanisms study of novel glucopyranoside derivatives
  作者：Meihang Chen、Deyu Hu、Xiangyang Li、Song Yang、Weiying Zhang、Pei Li、Baoan Song

  DOI：10.1016/j.bmcl.2015.07.068

  日期：2015.9

  Novel glucopyranoside derivatives were synthesized and evaluated for their antiviral activities against tobacco mosaic virus (TMV). Bioassay results indicated that some of the target compounds exhibited good in vivo antiviral activities against TMV. Among the title compounds, f6 showed appreciable inactivation effect against TMV, with the 50% effective concentration value (EC50) of 52.9 mu g/mL, which was better than that of ribavirin (145.1 mu g/mL). In addition, interaction between f6 and TMV-CP was characterized by fluorescence spectroscopy, isothermal titration calorimetry (ITC), and microscale thermophoresis (MST). Results showed that f6 bound to TMV-CP with micromole affinity, and thermodynamic parameters suggested that this interaction was typically endothermic and spontaneous, with 1: 1.53 ratio of TMV-CP to f6. Thus, the synthesized glucopyranoside derivatives containing 1,4-pentadien- 3-one moiety could be promising antiviral agents. (C) 2015 Elsevier Ltd. All rights reserved.
• Buck; Heilbron, Journal of the Chemical Society, 1922, vol. 121, p. 1098
  作者：Buck、Heilbron

  DOI：——

  日期：——
• MAKIN, S. M.;MARKINA, T. A.;BOJKO, I. I., ZH. ORGAN. XIMII, 24,(1988) N 11, S. 2419-2424
  作者：MAKIN, S. M.、MARKINA, T. A.、BOJKO, I. I.

  DOI：——

  日期：——