phenethyl 2-cyano-3-(3,4-dihydroxyphenyl)-2-propenoate | 132465-03-3

• 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: phenethyl 2-cyano-3-(3,4-dihydroxyphenyl)-2-propenoate
• 英文别名: (E)-phenethyl 2-cyano-3-(3,4-dihydroxyphenyl)acrylate；2-Cyano-3-(3,4-dihydroxy-phenyl)-acrylic acid phenethyl ester；2-phenylethyl (E)-2-cyano-3-(3,4-dihydroxyphenyl)prop-2-enoate
• CAS: 132465-03-3
• 化学式: C₁₈H₁₅NO₄
• 分子量: 309.321
• InChiKey: VSHGPCHQEFUWCE-XNTDXEJSSA-N

物化性质

• 沸点：
  550.4±50.0 °C(Predicted)
• 密度：
  1.320±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  90.6
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  氯甲酸乙酯 、 phenethyl 2-cyano-3-(3,4-dihydroxyphenyl)-2-propenoate 以 四氢呋喃 、 水 为溶剂， 生成 phenethyl 2-cyano-3-(3,4-diethoxycarbonyloxyphenyl)-2-propenoate
  参考文献：
  名称：

  Caffeic acid derivatives and pharmaceutical compositions containing the

  摘要：

  描述了由以下公式表示的咖啡酸衍生物：##STR1##其中R.sup.1和R.sup.2中的任一种是氢原子，C.sub.1 -C.sub.6烷基，--CO.sub.2 R.sup.4基团，或--CONR.sup.5 R.sup.6基团，其中R.sup.4，R.sup.5和R.sup.6是氢原子或特定基团，另一个是--CO.sub.2 R.sub.4基团或--CONF.sup.5 R.sup.6基团，或者R.sup.1和R.sup.2耦合在一起形成5-成员环，Y代表特定基团或原子，X代表取代或未取代的C.sub.6 -C.sub.10芳基，C.sub.7 -C.sub.12芳基烷基，杂环或杂环烷基基团，m和n代表特定整数，R.sub.3代表氢原子，羟基，--OCO.sub.2 R.sup.7基团，其中R.sup.7是氢原子或特定基团，或--OCONR.sup.8 R.sup.9基团，其中R.sup.8代表C.sub.1 -C.sub.6烷基基团，R.sup.9代表氢原子或C.sub.1 -C.sub.6烷基基团，以及其药学上可接受的盐。含有这些衍生物或盐的治疗剂对循环系统疾病有效。

  公开号：

  US05232941A1
• 作为产物：
  描述：

  苯乙醇 在 哌啶 、 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 phenethyl 2-cyano-3-(3,4-dihydroxyphenyl)-2-propenoate
  参考文献：
  名称：

  Synthesis and structure–activity relationship study of substituted caffeate esters as antinociceptive agents modulating the TREK-1 channel

  摘要：

  The TWIK-related K+ channel, TREK-1, has recently emerged as an attractive therapeutic target for the development of a novel class of analgesic drugs. It has been reported that TREK-1 -/- mice were more sensitive than wild-type mice to painful stimuli, suggesting that activation of TREK-1 could result in pain inhibition. Here we report the synthesis of a series of substituted caffeate esters (12a-u) based on the hit compound CDC 2 (cinnamyl 3,4-dihydroxyl-alpha-cyanocinnamate). These analogs were evaluated for their ability to modulate TREK-1 channel by electrophysiology and for their in vivo antinociceptive activity (acetic acid induced-writhing assay) leading to the identification a series of novel molecules able to activate TREK-1 and displaying potent analgesic activity in vivo. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.01.049

文献信息

• PAIN RELIEF COMPOUNDS
  申请人：ECOLE NATIONALE SUPERIEURE DE CHIMIE DE CLERMONT FERRAND

  公开号：US20150038466A1

  公开（公告）日：2015-02-05

  The present invention relates to the use of compounds for the treatment or prevention of pain in mammals, in particularly in human beings, and also to a process for preparing these compounds.

  本发明涉及使用化合物治疗或预防哺乳动物（尤其是人类）的疼痛，并且涉及一种制备这些化合物的方法。
• Derivative of caffeic acid and pharmaceutical composition containing the
  申请人：Suntory, Ltd.

  公开号：US05063243A1

  公开（公告）日：1991-11-05

  Novel derivatives of caffeic acid of the general formula (I): ##STR1## wherein X is hydrogen atom or hydroxy; R.sup.1 is hydrogen atom, a straight or branched alkyl or alkenyl having 1 to 20 carbon atoms or a group of the formula: --(CH.sub.2).sub.n --Z--R.sup.2 wherein n is an integer of 1 to 10; Z is oxygen atom, vinylene residue or a single bond; and R.sup.2 is a substituted or unsubstituted phenyl or heterocyclic residue is provided. These derivatives possess 12-lipoxygenase inhibitory activity and are useful for curing and preventing circulatory diseases. A pharmaceutical composition containing said derivtive is also provided.

  一般式(I)的咖啡酸新衍生物：其中X为氢原子或羟基；R.sup.1为氢原子、具有1至20个碳原子的直链或支链烷基或烯基，或具有以下结构的基团：--(CH.sub.2).sub.n --Z--R.sup.2，其中n为1至10的整数；Z为氧原子、乙烯基残基或单键；R.sup.2为取代或未取代的苯基或杂环残基。这些衍生物具有12-脂氧酶抑制活性，可用于治疗和预防循环系统疾病。还提供了含有该衍生物的药物组合物。
• Stereochemistry of Knoevenagel Condensation Products from Cyanoacetates and Aromatic Aldehydes.
  作者：Hidetsura CHO、Takashi IWASHITA、Mikiko HAMAGUCHI、Yoshiaki OYAMA

  DOI：10.1248/cpb.39.3341

  日期：——

  The C-13 long-range selective proton decoupling method and x-ray crystallographic analysis were employed to determine the stereochemistry of the caffeic acid derivatives, extremely potent 12-lipoxygenase inhibitors, synthesized from cyanoacetates and aromatic aldehydes. The ester group of 1 and 2 was found to be trans to the phenyl group.

  采用C-13长程选择性质子去耦合方法和X射线晶体学分析来确定从氰乙酸酯和芳香醛合成的咖啡酸衍生物的立体化学，这些衍生物是极具活性的12-脂氧合酶抑制剂。发现1和2的酯基与苯基呈反式排列。
• Caffeic acid derivatives and pharmaceutical compositions containing the same
  申请人：SUNTORY LIMITED

  公开号：EP0475214A1

  公开（公告）日：1992-03-18

  Described are caffeic acid derivatives represented by the following formula: wherein either one of R¹ and R² is a hydrogen atom, a C₁-C₆ alkyl group, a group -CO₂R⁴, or a group -CONR⁵R⁶, R⁴, R⁵ and R⁶ being either a hydrogen atom or a particular group, and the other is the group -CO₂R⁴ or the group -CONR⁵R⁶, or R¹ and R² are coupled together to represent a 5-membered ring so formed, Y represents a particular group or atom, X represents a substituted or unsubstituted C₆-C₁₀ aryl, C₇-C₁₂ aralkyl, heterocyclic or heterocyclic ring-alkyl group, m and n stand for particular integers, and R₃ represents a hydrogen atom, a hydroxyl group, a group -OCO₂R⁷, R⁷ being a hydrogen atom or a particular group, or a group -OCONR⁸R⁹, R⁸ representing a C₁-C₆ alkyl group and R⁹ representing a hydrogen atom or a C₁-C₆ alkyl group, and pharmaceutically acceptable salts thereof. Therapeutic agents containing the derivatives or salts are effective for diseases of the circulatory system.

  所述的咖啡酸衍生物由下式表示： 其中R¹和R²之一是氢原子、C₁-C₆烷基、基团-CO₂R⁴或基团-CONR⁵R⁶，R⁴、R⁵和R⁶是氢原子或特定基团、另一个是基团-CO₂R⁴或基团-CONR⁵R⁶，或 R¹ 和 R² 联在一起代表这样形成的五元环，Y 代表特定的基团或原子，X 代表取代或未取代的 C₆-C₁₀ 芳基、C₇-C₁₂ 芳基、杂环或杂环环烷基，m 和 n 代表特定整数，R₃ 代表氢原子、羟基、基团 -OCO₂R⁷、R⁷是氢原子或特定基团，或基团 -OCONR⁸R⁹，R⁸代表 C₁-C₆烷基，R⁹代表氢原子或 C₁-C₆烷基，及其药学上可接受的盐。含有这些衍生物或盐的治疗剂对循环系统疾病有效。
• Derivative of caffeic acid and pharmaceutical composition containing the same
  申请人：SUNTORY LIMITED

  公开号：EP0339671B1

  公开（公告）日：1994-08-10