(1E,4E)-1-(2-hydroxyphenyl)-5-(2-methoxyphenyl)penta-1,4-dien-3-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: (1E,4E)-1-(2-hydroxyphenyl)-5-(2-methoxyphenyl)penta-1,4-dien-3-one
• 英文别名: NSC-98938；1t-(2-hydroxy-phenyl)-5t-(2-methoxy-phenyl)-penta-1,4-dien-3-one；1t-(2-Hydroxy-phenyl)-5t-(2-methoxy-phenyl)-penta-1,4-dien-3-on
• 化学式: C₁₈H₁₆O₃
• 分子量: 280.323
• InChiKey: RNDFIDUOVAGOQF-DCIPZJNNSA-N

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：

  (1E,4E)-1-(2-hydroxyphenyl)-5-(2-methoxyphenyl)penta-1,4-dien-3-one 、 2,3,4,6-四乙酰氧基-alpha-D-吡喃葡萄糖溴化物 在 四丁基溴化铵 、 sodium hydroxide 作用下， 以 二氯甲烷 、 水 为溶剂， 以53%的产率得到(1E,4E)-1-(2-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)phenyl)-5-(2-methoxyphenyl)-1,4-pentadien-3-one
  参考文献：
  名称：

  Antiviral activity and interaction mechanisms study of novel glucopyranoside derivatives

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2015.07.068
• 作为产物：
  描述：

  水杨醛 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 生成 (1E,4E)-1-(2-hydroxyphenyl)-5-(2-methoxyphenyl)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

• Synthesis and Antiviral Bioactivity of Novel 3-((2-((1<i>E</i>,4<i>E</i>)-3-Oxo-5-arylpenta-1,4-dien-1-yl)phenoxy)methyl)-4(3<i>H</i>)-quinazolinone Derivatives
  作者：Juan Ma、Pei Li、Xiangyang Li、Qingcai Shi、Zhihua Wan、Deyu Hu、Linhong Jin、Baoan Song

  DOI：10.1021/jf502162y

  日期：2014.9.10

  A series of novel 3-((2-((1E,4E)-3-oxo-5-arylpenta-1,4-dien-1-yl)phenoxy)methyl)-4(3H)-quinazolinone derivatives were designed and synthesized. Antiviral bioassays indicated that a few of the compounds exhibited higher antiviral activities against tobacco mosaic virus (TMV) in vivo than the commercial agent ningnanmycin. In particular, compounds A5, A12, A25, and A27 possessed appreciable curative

  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。
• 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.
• On Disalicylideneacetone and Analogs
  作者：Peter T. Mora、Tibor Széki

  DOI：10.1021/ja01163a059

  日期：1950.7
• 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.