(E)-3-(3-methoxy-4-((2-methoxyethoxy)methoxy)phenyl)acrylic acid | 82929-84-8

• 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: (E)-3-(3-methoxy-4-((2-methoxyethoxy)methoxy)phenyl)acrylic acid
• 英文别名: 3-[3-methoxy-4-{(2-methoxyethoxy)methoxy}phenyl]-(E)-propenoic acid；(E)-3-[3-methoxy-4-(2-methoxyethoxymethoxy)phenyl]prop-2-enoic acid
• CAS: 82929-84-8
• 化学式: C₁₄H₁₈O₆
• 分子量: 282.293
• InChiKey: DOYQIFNDQMFQSA-GQCTYLIASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  20
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (E)-3-(3-methoxy-4-((2-methoxyethoxy)methoxy)phenyl)acrylic acid 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 (E)-2-(methylsulfonylthio)ethyl 3-(4-hydroxy-3-methoxyphenyl)acrylate
  参考文献：
  名称：

  肉桂酸和迷迭香碱的新型硫化衍生物，作为 STAT3 和 NF-κB 转录因子的抑制剂。

  摘要：

  合成了一组新的硫化药物混合物，主要源自咖啡酸、阿魏酸和迷迭香碱，并评估了它们抑制 STAT3 和 NF-κB 转录因子的能力。结果表明，大多数新的杂合化合物能够强烈且选择性地与 STAT3 结合，而母体药物在测试浓度下缺乏这种能力。其中一些还能够抑制HCT-116细胞系中的NF-κB转录活性，并在体外抑制HCT-116细胞增殖，IC50在微摩尔范围内，因此表明具有潜在的抗癌活性。总而言之，我们的研究描述了具有 STAT3/NF-κB 双重抑制活性的新衍生物的鉴定，这可能代表用于开发多靶点抗癌药物的热门化合物。

  DOI：

  10.1080/14756366.2017.1350658
• 作为产物：
  描述：

  阿魏酸 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-methoxy-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

• (2E,4E)-N-(4-(1H-Indol-3-yl)piperidin-1-yl)alkyl-5-(substituted phenyl)-2,4-pentadienamides as Antiallergic Agents with Antihistaminic and Anti Slow-Reacting Substance (SRS) Activities
  作者：Shinji Shigenaga、Takashi Manabe、Hiroshi Matsuda、Takashi Fujii、Masaaki Matsuo

  DOI：10.1002/ardp.19963290103

  日期：——

  compound with dual activities against histamine and slow‐reacting substance (SRS), we synthesized two types of indolylpiperidine derivatives, 3 and 4–20. Testing for in vivo antianaphylactic activity and for in vitro anti‐SRS activity revealed that (2E,4E)‐5‐(3,5‐dimethoxy‐4‐hydroxyphenyl)‐N‐(2‐(4‐(1H‐indol‐3‐yl)piperidin‐1‐yl)ethyl)‐2,4‐pentadienamide (11) exhibited potent dual activities with ED50 = 0

  作为我们研究的延伸，旨在发现一种对组胺和慢反应物质 (SRS) 具有双重活性的新型化合物，我们合成了两种类型的吲哚哌啶衍生物，3 和 4-20。体内抗过敏活性和体外抗 SRS 活性测试表明 (2E, 4E) -5- (3,5 - 二甲氧基 - 4 - 羟基苯基) -N- (2- (4- (1H - indole - 3 ‐Yl) 哌啶 ‐ 1 ‐ yl) 乙基) ‐2,4 - 戊二烯酰胺 (11) 表现出有效的双重活性，分别为 ED50 = 0.89 mg / kg 和 IC50 = 1.43 μM。然而，当在豚鼠中口服给药时，未改变的 11 的血浆浓度非常低。这一结果可以通过快速形成葡萄糖醛酸结合物来解释。
• Indolylpiperidine compounds, processes for the preparation thereof and
  申请人：Fujisawa Pharmaceutical Co., Ltd.

  公开号：US04935432A1

  公开（公告）日：1990-06-19

  The invention relates to new compounds, of antiallergic activity, of the formula: ##STR1## wherein R.sup.1 is aryl substituted with substituent(s) selected from the group consisting of hydroxy, protected hydroxy, halogen and lower alkoxy, A is lower alkylene, and B is lower alkenylene, or a pharmaceutically acceptable salt thereof.

  本发明涉及新的抗过敏活性化合物，其化学式为：##STR1## 其中，R.sup.1是芳基，其上带有羟基、保护羟基、卤素和较低的烷氧基等取代基；A是较低的烷基，B是较低的烯基，或其药学上可接受的盐。
• New indolylpiperidine compounds, processes for the preparation thereof and pharmaceutical composition comprising the same
  申请人：FUJISAWA PHARMACEUTICAL CO., LTD.

  公开号：EP0324431A1

  公开（公告）日：1989-07-19

  The present invention relates to new indolylpiperidine compounds represented by the following general formula (I): wherein R1 is aryl substituted with substituent(s) selected from the group consisting of hydroxy, protected hydroxy, halogen and lower alkoxy, A is lower alkylene, and B is lower alkenylene processes for the preparation thereof and pharmaceutical composition comprising the same.

  本发明涉及由以下通式(I)代表的新的吲哚基哌啶化合物： 其中 R1 是被选自羟基、受保护羟基、卤素和低级烷氧基的取代基取代的芳基、 A 是低级亚烷基，和 B 是低级烯烃 其制备工艺和包含其的药物组合物。
• Takano, Seiichi; Shishido, Kozo, Chemical and pharmaceutical bulletin, 1984, vol. 32, # 10, p. 3892 - 3899
  作者：Takano, Seiichi、Shishido, Kozo

  DOI：——

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

  DOI：——

  日期：——