2-氨基-4-(3,4-二甲氧基苯基)噻吩-3-甲腈 | 884497-31-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-氨基-4-(3,4-二甲氧基苯基)噻吩-3-甲腈
• 中文别名: 2-氨基-4-(3,4-二甲氧苯基)-3-氰基噻吩
• 英文名称: 2-amino-4-[3,4-bis(methyloxy)phenyl]-3-thiophenecarbonitrile
• 英文别名: 2-Amino-4-(3,4-dimethoxyphenyl)thiophene-3-carbonitrile
• CAS: 884497-31-8
• 化学式: C₁₃H₁₂N₂O₂S
• mdl: MFCD02854974
• 分子量: 260.316
• InChiKey: QEDSBOVKPQYQKK-UHFFFAOYSA-N

物化性质

• 沸点：
  438.4±45.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  96.5
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  2-氨基-4-(3,4-二甲氧基苯基)噻吩-3-甲腈 、 醋酸甲脒 以 N,N-二甲基甲酰胺 为溶剂， 以84 %的产率得到5-(3,4-dimethoxyphenyl)thieno[2,3-d]pyrimidin-4-amine
  参考文献：
  名称：

  2-氨基-4-芳基噻吩-3-甲腈和乙酸甲脒作为合成5-芳基噻吩并[2,3-d]嘧啶-4-胺的关键结构单元

  摘要：

  我们试图建立一种通过三步反应合成5-芳基噻吩并[2,3- d ]嘧啶-4-胺类似物的方法，并考察了溶剂、时间和温度的变化。开发了一种新的条件，用于制备取代的 2-氨基噻吩，采用 Knoevenagel 缩合，然后采用 Gewald 方法，最后一步使用乙酸甲脒形成噻吩并[2,3- d ]嘧啶。所有合成的5-芳基噻吩并[2,3- d ]嘧啶-4-胺都是未知的，并通过IR、1 H-NMR、13 C-NMR和CHN分析进行了表征。

  DOI：

  10.1002/jhet.4727
• 作为产物：
  描述：

  2-(3,4-dimethoxyphenyl)malononitrile 在 1,2,3,4,5,6,7,8-八硫杂环辛烷 、 碳酸氢钠 作用下， 以 四氢呋喃 、 水 为溶剂， 以70 %的产率得到2-氨基-4-(3,4-二甲氧基苯基)噻吩-3-甲腈
  参考文献：
  名称：

  2-氨基-4-芳基噻吩-3-甲腈和乙酸甲脒作为合成5-芳基噻吩并[2,3-d]嘧啶-4-胺的关键结构单元

  摘要：

  我们试图建立一种通过三步反应合成5-芳基噻吩并[2,3- d ]嘧啶-4-胺类似物的方法，并考察了溶剂、时间和温度的变化。开发了一种新的条件，用于制备取代的 2-氨基噻吩，采用 Knoevenagel 缩合，然后采用 Gewald 方法，最后一步使用乙酸甲脒形成噻吩并[2,3- d ]嘧啶。所有合成的5-芳基噻吩并[2,3- d ]嘧啶-4-胺都是未知的，并通过IR、1 H-NMR、13 C-NMR和CHN分析进行了表征。

  DOI：

  10.1002/jhet.4727

文献信息

• [EN] NOVEL COMPOUNDS<br/>[FR] NOUVEAUX COMPOSÉS
  申请人：GLAXO WELLCOME MFG PTE LTD

  公开号：WO2011075559A1

  公开（公告）日：2011-06-23

  The present invention relates to novel NADPH oxidase II inhibitors and their use in the treatment of diseases mediated by the NADPH oxidase II enzyme.

  本发明涉及新型NADPH氧化酶II抑制剂及其在治疗由NADPH氧化酶II酶介导的疾病中的应用。
• NOVEL COMPOUNDS
  申请人：Chen Deborah

  公开号：US20120252805A1

  公开（公告）日：2012-10-04

  The present invention relates to novel NADPH oxidase II inhibitors and their use in the treatment of diseases mediated by the NADPH oxidase II enzyme.

  本发明涉及新型NADPH氧化酶II抑制剂及其在治疗由NADPH氧化酶II酶介导的疾病中的应用。
• Basic Ionic Liquid [bmIm]OH–Mediated Gewald Reaction as Green Protocol for the Synthesis of 2-Aminothiophenes
  作者：Venkata Rao Kaki、Raghuram Rao Akkinepalli、Pran Kishore Deb、Mallikarjuna Rao Pichika

  DOI：10.1080/00397911.2014.951898

  日期：2015.1.2

  A simple, efficient, and environmental friendly procedure was developed based on the Gewald reaction for the synthesis of 2-aminothiophenes using a basic ionic liquid [bmIm]OH as both catalyst and solvent. Besides being a green protocol, the method offers advantages of successful synthesis of a variety of alkyl, aryl, alkoxy, and alkylamino-2-aminothiophenes in good yields.
• Synthesis and structure–activity relationships of 2-amino-3-carboxy-4-phenylthiophenes as novel atypical protein kinase C inhibitors
  作者：Paul M. Titchenell、H.D. Hollis Showalter、Jean-François Pons、Alistair J. Barber、Yafei Jin、David A. Antonetti

  DOI：10.1016/j.bmcl.2013.03.019

  日期：2013.5

  Recent evidence suggests atypical protein kinase C (aPKC) isoforms are required for both TNF- and VEGF-induced breakdown of the blood-retinal barrier (BRB) and endothelial permeability to 70 kDa dextran or albumin. A chemical library screen revealed a series of novel small molecule phenylthiophene based inhibitors of aPKC isoforms that effectively block permeability in cell culture and in vivo. In an effort to further elucidate the structural requirements of this series of inhibitors, we detail in this study a structure-activity relationship (SAR) built on screening hit 1, which expands on our initial pharmacophore model. The biological activity of our analogues was evaluated in models of bona fide aPKC-dependent signaling including NF kappa B driven-gene transcription as a marker for an inflammatory response and VEGF/TNF-induced vascular endothelial permeability. The EC50 for the most efficacious inhibitors (6, 32) was in the low nanomolar range in these two cellular assays. Our study demonstrates the key structural elements that confer inhibitory activity and highlights the requirement for electron-donating moieties off the C-4 aryl moiety of the 2-amino-3-carboxy-4-phenylthiophene backbone. These studies suggest that this class has potential for further development into small molecule aPKC inhibitors with therapeutic efficacy in a host of diseases involving increased vascular permeability and inflammation. (C) 2013 Elsevier Ltd. All rights reserved.
• Compounds, Formulations, and Methods of Protein Kinase C Inhibition
  申请人：Antonetti David A.

  公开号：US20120302561A1

  公开（公告）日：2012-11-29

  The invention provides a method of inhibiting atypical protein kinase C (aPKC) comprising contacting an aPKC with a compound having a structure selected from the group consisting of structural formulas (I) to (IX). The invention further provides a method of inhibiting or reducing vascular permeability. The method comprising administering to a subject a composition comprising an amount of a compound having a structure selected from the group consisting of structural formulas (I) to (IX) effective to inhibit or reduce vascular permeability. A method of treating or preventing a disease or disorder characterized by abnormal vascular permeability, a method of inhibiting angiogenesis, a method of inhibiting cancer cell proliferation, a formulation, and a method of preparing a formulation also are provided.