(2E)-3-{4-[(2-chlorobenzyl)oxy]-3-methoxyphenyl}prop-2-enoic acid

• 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: (2E)-3-{4-[(2-chlorobenzyl)oxy]-3-methoxyphenyl}prop-2-enoic acid
• 英文别名: (E)-3-[4-[(2-chlorophenyl)methoxy]-3-methoxyphenyl]prop-2-enoic acid
• 化学式: C₁₇H₁₅ClO₄
• 分子量: 318.757
• InChiKey: TWWBSHWGJXCZDS-VQHVLOKHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  diethyl 1-aminophenylmethylphosphonate 、 (2E)-3-{4-[(2-chlorobenzyl)oxy]-3-methoxyphenyl}prop-2-enoic acid 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以52.2%的产率得到diethyl (E)-((3-(4-((2-chlorobenzyl)oxy)-3-methoxyphenyl)acrylamido)(phenyl)methyl)phosphonate
  参考文献：
  名称：

  Novel α,β-unsaturated amide derivatives bearing α-amino phosphonate moiety as potential antiviral agents

  摘要：

  Based on flexible construction and broad bioactivity of ferulic acid, a series of novel alpha, beta-unsaturated amide derivatives bearing alpha-aminophosphonate moiety were designed, synthesized and systematically evaluated for their antiviral activity. Bioassay results indicated that some compounds exhibited good antiviral activities against cucumber mosaic virus (CMV) and tobacco mosaic virus (TMV) in vivo. Especially, compound g18 showed excellent curative and protective activities against CMV, with halfmaximal effective concentration (EC50) values of 284.67 mu g/mL and 216.30 mu g/mL, which were obviously superior to that of Ningnanmycin (352.08 mu g/mL and 262.53 mu g/mL). Preliminary structure-activity relationships (SARs) analysis revealed that the introduction of electron-withdrawing group at the 2-position or 4-position of the aromatic ring is favorable for antiviral activity. Present work provides a promising template for development of potential inhibitor of plant virus. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2017.08.048
• 作为产物：
  描述：

  阿魏酸甲酯 在 potassium carbonate 、 sodium hydroxide 作用下， 以 水 、 乙腈 为溶剂， 生成 (2E)-3-{4-[(2-chlorobenzyl)oxy]-3-methoxyphenyl}prop-2-enoic acid
  参考文献：
  名称：

  Novel α,β-unsaturated amide derivatives bearing α-amino phosphonate moiety as potential antiviral agents

  摘要：

  Based on flexible construction and broad bioactivity of ferulic acid, a series of novel alpha, beta-unsaturated amide derivatives bearing alpha-aminophosphonate moiety were designed, synthesized and systematically evaluated for their antiviral activity. Bioassay results indicated that some compounds exhibited good antiviral activities against cucumber mosaic virus (CMV) and tobacco mosaic virus (TMV) in vivo. Especially, compound g18 showed excellent curative and protective activities against CMV, with halfmaximal effective concentration (EC50) values of 284.67 mu g/mL and 216.30 mu g/mL, which were obviously superior to that of Ningnanmycin (352.08 mu g/mL and 262.53 mu g/mL). Preliminary structure-activity relationships (SARs) analysis revealed that the introduction of electron-withdrawing group at the 2-position or 4-position of the aromatic ring is favorable for antiviral activity. Present work provides a promising template for development of potential inhibitor of plant virus. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2017.08.048

文献信息

• Novel α,β-unsaturated amide derivatives bearing α-amino phosphonate moiety as potential antiviral agents
  作者：Xianmin Lan、Dandan Xie、Limin Yin、Zhenzhen Wang、Jin Chen、Awei Zhang、Baoan Song、Deyu Hu

  DOI：10.1016/j.bmcl.2017.08.048

  日期：2017.9

  Based on flexible construction and broad bioactivity of ferulic acid, a series of novel alpha, beta-unsaturated amide derivatives bearing alpha-aminophosphonate moiety were designed, synthesized and systematically evaluated for their antiviral activity. Bioassay results indicated that some compounds exhibited good antiviral activities against cucumber mosaic virus (CMV) and tobacco mosaic virus (TMV) in vivo. Especially, compound g18 showed excellent curative and protective activities against CMV, with halfmaximal effective concentration (EC50) values of 284.67 mu g/mL and 216.30 mu g/mL, which were obviously superior to that of Ningnanmycin (352.08 mu g/mL and 262.53 mu g/mL). Preliminary structure-activity relationships (SARs) analysis revealed that the introduction of electron-withdrawing group at the 2-position or 4-position of the aromatic ring is favorable for antiviral activity. Present work provides a promising template for development of potential inhibitor of plant virus. (C) 2017 Elsevier Ltd. All rights reserved.