(E)-3-{3,5-dimethoxy-4-[(2-methoxyethoxy)methoxy]phenyl}acrylic acid | 101619-93-6

• 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: (E)-3-{3,5-dimethoxy-4-[(2-methoxyethoxy)methoxy]phenyl}acrylic acid
• 英文别名: 3,5-dimethoxy-4-(β-methoxyethoxymethoxy)cinnamic acid；(E)-3-[3,5-dimethoxy-4-(2-methoxyethoxymethoxy)phenyl]prop-2-enoic acid
• CAS: 101619-93-6
• 化学式: C₁₅H₂₀O₇
• 分子量: 312.32
• InChiKey: BVGJHKNVOJITGB-SNAWJCMRSA-N

物化性质

• 沸点：
  471.7±45.0 °C(Predicted)
• 密度：
  1.204±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  22
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  83.4
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (E)-3-{3,5-dimethoxy-4-[(2-methoxyethoxy)methoxy]phenyl}acrylic acid 在 甲酸 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 水 、 乙腈 为溶剂， 反应 30.0h， 生成 N-(5'-deoxyadenosin-5'-yl)-N'-[(E)-3-(4-hydroxy-3,5-dimethoxyphenyl)acryloyl]sulfamide
  参考文献：
  名称：

  Synthesis and inhibitory activity of mechanism-based 4-coumaroyl-CoA ligase inhibitors

  摘要：

  4-Coumaroyl-CoA ligase (4CL) is ubiquitous in the plant kingdom, and plays a central role in the biosynthesis of phenylpropanoids such as lignins, flavonoids, and coumarins. 4CL catalyzes the formation of the coenzyme A thioester of cinnamates such as 4-coumaric, caffeic, and ferulic acids, and the regulatory position of 4CL in the phenylpropanoid pathway renders the enzyme an attractive target that controls the composition of phenylpropanoids in plants. In this study, we designed and synthesized mechanism- based inhibitors for 4CL in order to develop useful tools for the investigation of physiological functions of 4CL and chemical agents that modulate plant growth with the ultimate goal to produce plant biomass that exhibits features that are beneficial to humans. The acylsulfamide backbone of the inhibitors in this study was adopted as a mimic of the acyladenylate intermediates in the catalytic reaction of 4CL. These acylsulfamide inhibitors and the important synthetic intermediates were fully characterized using two-dimensional NMR spectroscopy. Five 4CL proteins with distinct substrate specificity from four plant species, i.e., Arabidopsis thaliana, Glycine max (soybean), Populus trichocarpa (poplar), and Petunia hybrida (petunia), were used to evaluate the inhibitory activity, and the half-maximum inhibitory concentration (IC50) of each acylsulfamide in the presence of 4-coumaric acid (100 mu M) was determined as an index of inhibitory activity. The synthetic acylsulfamides used in this study inhibited the 4CLs with IC50 values ranging from 0.10 to 722 mM, and the IC50 values of the most potent inhibitors for each 4CL were 0.10-2.4 mM. The structure-activity relationship observed in this study revealed that both the presence and the structure of the acyl group of the synthetic inhibitors strongly affect the inhibitory activity, and indicates that 4CL recognizes the acylsulfamide inhibitors as acyladenylate mimics. (C) 2018 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2018.04.006
• 作为产物：
  描述：

  芥子酸 在 N,N-二异丙基乙胺 、 sodium hydroxide 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 24.5h， 生成 (E)-3-{3,5-dimethoxy-4-[(2-methoxyethoxy)methoxy]phenyl}acrylic acid
  参考文献：
  名称：

  Synthesis and inhibitory activity of mechanism-based 4-coumaroyl-CoA ligase inhibitors

  摘要：

  4-Coumaroyl-CoA ligase (4CL) is ubiquitous in the plant kingdom, and plays a central role in the biosynthesis of phenylpropanoids such as lignins, flavonoids, and coumarins. 4CL catalyzes the formation of the coenzyme A thioester of cinnamates such as 4-coumaric, caffeic, and ferulic acids, and the regulatory position of 4CL in the phenylpropanoid pathway renders the enzyme an attractive target that controls the composition of phenylpropanoids in plants. In this study, we designed and synthesized mechanism- based inhibitors for 4CL in order to develop useful tools for the investigation of physiological functions of 4CL and chemical agents that modulate plant growth with the ultimate goal to produce plant biomass that exhibits features that are beneficial to humans. The acylsulfamide backbone of the inhibitors in this study was adopted as a mimic of the acyladenylate intermediates in the catalytic reaction of 4CL. These acylsulfamide inhibitors and the important synthetic intermediates were fully characterized using two-dimensional NMR spectroscopy. Five 4CL proteins with distinct substrate specificity from four plant species, i.e., Arabidopsis thaliana, Glycine max (soybean), Populus trichocarpa (poplar), and Petunia hybrida (petunia), were used to evaluate the inhibitory activity, and the half-maximum inhibitory concentration (IC50) of each acylsulfamide in the presence of 4-coumaric acid (100 mu M) was determined as an index of inhibitory activity. The synthetic acylsulfamides used in this study inhibited the 4CLs with IC50 values ranging from 0.10 to 722 mM, and the IC50 values of the most potent inhibitors for each 4CL were 0.10-2.4 mM. The structure-activity relationship observed in this study revealed that both the presence and the structure of the acyl group of the synthetic inhibitors strongly affect the inhibitory activity, and indicates that 4CL recognizes the acylsulfamide inhibitors as acyladenylate mimics. (C) 2018 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2018.04.006

文献信息

• Amide derivatives and 5-lipoxygenase inhibitors containing the same as an active ingredient
  申请人：TERUMO KABUSHIKI KAISHA trading as TERUMO CORPORATION

  公开号：EP0157420A2

  公开（公告）日：1985-10-09

  According to the invention, there are provided novel amide derivatives and 5-lipoxygenase inhibitors containing the same as an effective ingredient. The above-mentioned compounds of the invention have been demonstrated to possess 5-lipoxygenase-inhibiting activities. These compounds can inhibit the production of leucotrienes such as LTC4 and LTD4 which are allergy-inducing factors by inhibiting the activity of 5-lipoxygenase. Accordingly, the amide derivatives can be used as 5-lipoxygenase inhibitors effective for allergic asthma, allergic rhinitis and the like.

  根据本发明，提供了新型酰胺衍生物和以酰胺衍生物为有效成分的 5-脂氧合酶抑制剂。 上述本发明化合物已被证实具有 5-脂氧合酶抑制活性。 这些化合物可以通过抑制 5-脂氧合酶的活性来抑制白三烯（如 LTC4 和 LTD4）的产生，而白三烯是过敏诱因。 因此，酰胺衍生物可用作 5-脂氧合酶抑制剂，对过敏性哮喘、过敏性鼻炎等有效。
• VAKABAYASI, TOSIO;TAKAI, MAKOTO;ARAI, DZYUNITIRO;ITIKAVA, XIDEHDZI;MUROTA+
  作者：VAKABAYASI, TOSIO、TAKAI, MAKOTO、ARAI, DZYUNITIRO、ITIKAVA, XIDEHDZI、MUROTA+

  DOI：——

  日期：——
• ——
  作者：VAKABAYASI TOSIO、 TAKAI MAKOTO、 ARAI DZYUNITIRO、 ITIKAVA XIDEHDZI、 MUROTA+

  DOI：——

  日期：——
• US4673684A
  申请人：——

  公开号：US4673684A

  公开（公告）日：1987-06-16