(E)-4-(3,4-dimethylphenyl)-4-oxo-2-butenoic acid | 129904-81-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (E)-4-(3,4-dimethylphenyl)-4-oxo-2-butenoic acid
• 英文别名: (E)-4-(3,4-dimethylphenyl)-4-oxobut-2-enoic acid
• CAS: 129904-81-0
• 化学式: C₁₂H₁₂O₃
• 分子量: 204.225
• InChiKey: WKLVCCFVWXJZFO-AATRIKPKSA-N

物化性质

• 沸点：
  394.4±42.0 °C(Predicted)
• 密度：
  1.168±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-4-(3,4-dimethylphenyl)-4-oxo-2-butenoic acid 生成 2-acetylthio-3-(3,4-dimethylbenzoyl)propionic acid
  参考文献：
  名称：

  3-benzoyl-2-mercaptopropionic acid derivatives

  摘要：

  由一般公式##STR1##表示的3-苯甲酰基-2-巯基丙酸衍生物（其中，X代表氢原子、卤原子、羟基、较低的烷基或较低的烷氧基，Y代表氢原子、卤原子、较低的烷基或较低的烷氧基，Z代表氢原子或酰基，R代表氢原子或较低的烷基）。这些化合物具有免疫调节功能，对治疗由异常免疫功能引起的疾病有效。

  公开号：

  US04594197A1
• 作为产物：
  描述：

  马来酸酐 、 邻二甲苯 在 aluminum (III) chloride 作用下， 以 二氯甲烷 为溶剂， 生成 (E)-4-(3,4-dimethylphenyl)-4-oxo-2-butenoic acid
  参考文献：
  名称：

  Catalytic Conjugate Addition of Indoles to 4-Aryl-4-oxobut-2-enoates by FeCl₃

  摘要：

  在温和条件下，使用FeCl3作为催化剂，成功实现了吲哚对4-芳基-4-氧基丁-2-烯酸酯的共轭加成反应。该反应具有很高的区域选择性，产出了多种新型3取代吲哚，得率良好至优异。

  DOI：

  10.1246/cl.2008.1284

文献信息

• Synthesis, study of the structure, and modification of the products of the reaction of 4-aryl-4-oxobut-2-enoic acids with thiourea
  作者：Nadezhda N. Kolos、Nikolai V. Nazarenko、Svetlana V. Shishkina、Andrey O. Doroshenko、Elena G. Shvets、Maksim A. Kolosov、Fedor G. Yaremenko

  DOI：10.1007/s10593-020-02798-y

  日期：2020.9

  A number of previously undescribed derivatives of 2-amino-5-(2-aryl-2-oxoethyl)thiazol-4(5H)-one containing electron-donating substituents in the aromatic ring were synthesized by the reaction of (E)-4-aryl-4-oxobut-2-enoic acids with thiourea. Reduction of the reaction products with NaBH4 yielded diastereomeric alcohols, whereas bromination in AcOH was accompanied by elimination of HBr and the formation

  通过（E）-的反应，合成了许多先前未描述的2-氨基-5-（2-芳基-2-氧代乙基）噻唑-4（5H）-在芳族环中含有给电子取代基的衍生物。4-芳基-4-氧代丁-2-烯酸与硫脲。用NaBH 4还原反应产物可生成非对映异构醇，而在AcOH中溴化则伴随着HBr的消除和（Z）-2-氨基-5-（2-芳基-2-氧代亚乙基）噻唑-4（5）的形成。H）-一个。
• An Efficient Synthesis of β-Aroylacrylic Acid Ethyl Ester by the Friedel–Crafts Reaction in the Presence of Diethyl Sulfate
  作者：Ken-ichi Onoue、Taichi Shintou、Chang Shan Zhang、Isamu Itoh

  DOI：10.1246/cl.2006.22

  日期：2006.1

  An β-Aroylacrylic acid ethyl ester such as ethyl (E)-4-(3,4-dimethoxyphenyl)-4-oxo-2-butenoate (1) can be obtained in good yield and with excellent purity by way of the Friedel–Crafts reaction in w...

  β-芳酰基丙烯酸乙酯如 (E)-4-(3,4-二甲氧基苯基)-4-氧代-2-丁烯酸乙酯 (1) 可以通过 Friedel- 法以良好的收率和优异的纯度获得手工艺反应在...
• Design, synthesis and biological evaluation of benzoylacrylic acid shikonin ester derivatives as irreversible dual inhibitors of tubulin and EGFR
  作者：Wen-Xue Sun、Hong-Wei Han、Min-Kai Yang、Zhong-Ling Wen、Yin-Song Wang、Jiang-Yan Fu、Yun-Ting Lu、Ming-Yue Wang、Jia-Xin Bao、Gui-Hua Lu、Jin-Liang Qi、Xiao-Ming Wang、Hong-Yan Lin、Yong-Hua Yang

  DOI：10.1016/j.bmc.2019.115153

  日期：2019.12

  In this study, a series of shikonin derivatives combined with benzoylacrylic had been designed and synthesized, which showed an inhibitory effect on both tubulin and the epidermal growth factor receptor (EGFR). In vitro EGFR and cell growth inhibition assay demonstrated that compound PMMB-317 exhibited the most potent anti-EGFR (IC50 = 22.7 nM) and anti-proliferation activity (IC50 = 4.37 μM) against

  在这项研究中，已经设计并合成了一系列紫草素衍生物与苯甲酰基丙烯酸的组合，对微管蛋白和表皮生长因子受体（EGFR）均显示出抑制作用。体外EGFR和细胞生长抑制试验表明，化合物PMMB-317对A549细胞系表现出最强的抗EGFR（IC 50 = 22.7 nM）和抗增殖活性（IC 50 = 4.37μM）阿法替尼（EGFR，IC 50 = 15.4 nM; A549，IC 50= 6.32μM）。我们的机理研究结果表明，PMMB-317可以剂量和时间依赖性诱导A549细胞凋亡，同时线粒体膜电位（MMP）降低，ROS的产生以及凋亡相关蛋白水平的改变。另外，PMMB-317可通过阻断有丝分裂原活化蛋白MAPK途径和抗凋亡激酶AKT途径下游的信号转导，在G2 / M期阻滞细胞周期，诱导细胞凋亡，并抑制EGFR活性。通常，这种结果与阿法替尼相当。此外，PMMB-317可以通过Wnt / β抑制A54
• 3-Benzoyl-2-mercaptopropionic acid derivaties
  申请人：TAISHO PHARMACEUTICAL CO. LTD

  公开号：EP0138349A1

  公开（公告）日：1985-04-24

  3-Benzoyl-2-mercaptopropionic acid derivatives represented by the general formula (wherein, X represents a hydrogen atom, a halogen atom, hydroxy group, a lower alkyl group or a lower alkoxy group, Y represents a hydrogen atom, a halogen atom, a lower alkyl group or a lower alkoxy group, Z represents a hydrogen atom or an acyl group, and R represents a hydrogen atom or a lower alkyl group) have immunomodulative function and are effective for treatment of diseases caused by abnormal immunofunction.

  由通式（其中，X 代表氢原子、卤素原子、羟基、低级烷基或低级烷氧基，Y 代表氢原子、卤素原子、低级烷基或低级烷氧基，Z 代表氢原子或酰基，R 代表氢原子或低级烷基）表示的 3-苯甲酰基-2-巯基丙酸衍生物具有免疫调节功能，可有效治疗由免疫功能异常引起的疾病。
• 2-[(Carboxymethyl)sulfanyl]-4-oxo-4-arylbutanoic Acids Selectively Suppressed Proliferation of Neoplastic Human HeLa Cells. A SAR/QSAR Study
  作者：Branko J. Drakulić、Zorica D. Juranić、Tatjana P. Stanojković、Ivan O. Juranić

  DOI：10.1021/jm0502889

  日期：2005.8.1

  A series of twenty alkyl-, halo-, and methoxy-aryl-substituted 2-[(carboxymethyl)sulfanyl]-4-oxo-4-arylbutanoic acids were synthesized. The new compounds, called CSAB, suppressed proliferation of human cervix carcinoma, HeLa cells, in vitro in a concentration range of 0.644 to 29.48 mu M/L. Two compounds exhibit antiproliferative activity in sub-micromolar concentrations (16, 19). Five compounds act in low micromolar concentrations (< 2 mu M/L). The most active compounds exert lower cytotoxicity toward healthy human peripheral blood mononuclear cells (PBMC and PBMC+PHA) (selectivity indexes > 10). A strong structure-activity relationship, using estimated log P values and BCUT descriptors, was observed.