4-(4-methoxyphenyl)-2-oxo-3-butenoic acid | 17451-21-7

• 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: 4-(4-methoxyphenyl)-2-oxo-3-butenoic acid
• 英文别名: p-methoxybenzylidenepyruvic acid；4-(p-Methoxyphenyl)-2-Oxo-3-Butenoic Acid；4-(4-methoxyphenyl)-2-oxobut-3-enoic acid
• CAS: 17451-21-7
• 化学式: C₁₁H₁₀O₄
• 分子量: 206.198
• InChiKey: SHVBLFWLPMOIIO-UHFFFAOYSA-N

物化性质

• 熔点：
  131 °C
• 沸点：
  375.4±34.0 °C(Predicted)
• 密度：
  1.267±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(4-methoxyphenyl)-2-oxo-3-butenoic acid 在 氯仿 、 溴 作用下， 生成 3,4-dibromo-4-(4-methoxy-phenyl)-2-oxo-butyric acid
  参考文献：
  名称：

  Reimer, Journal of the American Chemical Society, 1926, vol. 48, p. 2460

  摘要：

  DOI：
• 作为产物：
  描述：

  2-ethylimino-4-(4-methoxy-phenyl)-but-3-enoic acid 在 盐酸 作用下， 生成 4-(4-methoxyphenyl)-2-oxo-3-butenoic acid
  参考文献：
  名称：

  Skita; Wulff, Justus Liebigs Annalen der Chemie, 1927, vol. 455, p. 35

  摘要：

  DOI：
• 作为试剂：
  描述：

  sodium pyruvate 、 4-甲氧基苯甲醛 在 4-(4-methoxyphenyl)-2-oxo-3-butenoic acid 、 乙酸乙酯 作用下， 以 sodium hydroxide 为溶剂， 反应 24.0h， 生成 4-(4-methoxyphenyl)-2-oxo-3-butenoic acid
  参考文献：
  名称：

  Process for preparing benzylpyruvic acids and esters

  摘要：

  公开了一种连续的、非隔离的制备苯甲基丙酮酸和苯甲基丙酮酸酯的方法。所得的苯甲基丙酮酸和酯可用作中间体，制备用于治疗高血压的羧基烷基二肽化合物，这些化合物用作血管紧张素转换酶（ACE）抑制剂。

  公开号：

  US04956490A1

文献信息

• Arylidene pyruvic acids motif in the synthesis of new thiopyrano[2,3-<i>d</i>]thiazoles as potential biologically active compounds
  作者：Andrii Lozynskyi、Borys Zimenkovsky、Ihor Nektegayev、Roman Lesyk

  DOI：10.1515/hc-2014-0204

  日期：2015.2.1

  Novel rel-(5R,6S,7S)-2-oxo-5,7-diaryl-3,5,6,7-tetrahydro-2H-thiopyrano[2,3-d]thiazol-6-yl-oxo-acetic acids were synthesized in 52–70% yields via regioselective and diastereoselective hetero-Diels-Alder reaction of 5-arylidene-4-thioxo-2-thiazolidinones with a series of arylidene pyruvic acids. The synthesized compounds were evaluated for anticancer activity in NCI60 cancer cell lines and for antiexudative activity on the carrageenan edema model in rats. Biological screening data led to identification of 3e as having moderate antitumor activity on the colon cancer HT-29 cell line and of 3b as having promising antiexudative effect.

  新型rel-(5R,6S,7S)-2-氧代-5,7-二芳基-3,5,6,7-四氢-2H-噻吩并[2,3-d]噻唑-6-基-氧代-乙酸在52-70%的产率下通过5-芳基亚亚甲基-4-硫代-2-噻唑烷酮与一系列芳基亚亚甲基丙酮酸的区域选择性和对映选择性异-Diels-Alder反应合成。合成的化合物在NCI60癌细胞系中进行了抗癌活性评价，并在大鼠卡拉胶水肿模型上进行了抗渗出活性评价。生物筛选数据表明3e在结肠癌HT-29细胞系中具有中等抗肿瘤活性，3b具有有希望的抗渗出效果。

• Arylidenepyruvic Acid Thiosemicarbazone and Thiazoline Derivatives As Potential Antimicrobial Agents
  作者：A.-Mohsen M. E.Omar、Ibrahim M. Labouta、M. Gabr Kasem、J. Bourdais

  DOI：10.1002/jps.2600721034

  日期：1983.10

  Two novel series of arylidenepyruvic acid thiosemicarbazone and thiazoline derivatives were synthesized and evaluated as potential antimicrobial agents. These substances did not exhibit any significant antibacterial effects when tested against a variety of microorganisms.

  合成了两个新系列的亚芳基丙酮酸硫代半碳酰胺和噻唑啉衍生物，并将其作为潜在的抗菌剂进行了评估。当针对多种微生物进行测试时，这些物质没有表现出任何明显的抗菌作用。
• SUBSTITUTED PYRAZOLO[3,4-b]PYRIDIN-6-CARBOXYLIC ACIDS AND METHOD OF USE
  申请人：AbbVie S.à.r.l.

  公开号：US20170101406A1

  公开（公告）日：2017-04-13

  The present invention provides for compounds of formula (I) wherein R 1 , R 2 , R 3 , and R 4 have any of the values defined in the specification, and pharmaceutically acceptable salts thereof, that are useful as agents in the treatment of diseases and conditions mediated and modulated by CFTR, including cystic fibrosis, Sjögren's syndrome, pancreatic insufficiency, chronic obstructive lung disease, and chronic obstructive airway disease. Also provided are pharmaceutical compositions comprised of one or more compounds of formula (I).

  本发明提供了式（I）的化合物 其中R 1 ，R 2 ，R 3 和R 4 具有规范中定义的任何值，以及其药学上可接受的盐，这些化合物在治疗由CFTR介导和调节的疾病和症状中是有用的，包括囊性纤维化、Sjögren综合征、胰腺功能不全、慢性阻塞性肺病和慢性阻塞性气道疾病。还提供了由一个或多个式（I）的化合物组成的药物组合物。
• Heterocyclization Reactions of 3-methylisoxazol-5-amine with Pyruvic Acid Derivatives Using Classical and Non-classical Methods of Activation
  作者：Alisa D. Morozova、Elena A. Muravyova、Sergey M. Desenko、Vladimir I. Musatov、Daria V. Yedamenko、Valentin A. Chebanov

  DOI：10.1007/s10593-017-1989-9

  日期：2016.11

  between 3-methylisoxazol-5-amine and pyruvic acid derivatives were studied both by using classical methods of activation, as well as under microwave irradiation and ultrasonication. It was shown that the reactions with esters of arylidene pyruvic acids could lead to the formation of three different types of heterocyclic systems, while in the case of arylidene pyruvic acid a very insignificant conversion

  通过使用经典的活化方法，以及在微波辐射和超声处理下，研究了3-甲基异恶唑-5-胺与丙酮酸衍生物之间的双组分和多组分相互作用。结果表明，与亚芳基丙酮酸的酯反应可导致形成三种不同类型的杂环系统，而在亚芳基丙酮酸的情况下，起始化合物向异恶唑[5,4- b ]的转化非常微不足道。由于3-甲基异恶唑-5-胺的低稳定性，观察到吡啶羧酸。
• β-Carbolines: synthesis of harmane, harmine alkaloids and their structural analogs by thermolysis of 4-aryl-3-azidopyridines and investigation of their optical properties
  作者：Vladislav Yu. Shuvalov、Valeriya А. Elisheva、Anastasiya S. Belousova、Evgenii V. Arshinov、Larisa V. Glyzdinskaya、Marina А. Vorontsova、Sergei А. Chernenko、Aleksander S. Fisyuk、Galina P. Sagitullina

  DOI：10.1007/s10593-020-02625-4

  日期：2020.1

  their fluorescent properties in the study of their interaction with DNA and other biological targets, as well as with drug delivery vehicles. A new general method for the synthesis of harmane, harmine, and their structural analogs by thermolysis of substituted 4-aryl-3-azidopyridines was developed, and their optical properties were studied.

  对β-咔啉的兴趣是由这些化合物的生物活性以及在研究其与DNA和其他生物靶标以及与药物递送载体的相互作用中使用荧光性质引起的。提出了一种通过热取代取代的4-芳基-3-叠氮基吡啶合成海藻烷，氨苄及其结构类似物的新方法，并对其光学性质进行了研究。