6-bromo-N-(thiophen-2-ylmethyl)quinazolin-4-amine | 1225440-72-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 6-bromo-N-(thiophen-2-ylmethyl)quinazolin-4-amine
• 英文别名: 6-Bromo-N-(thiophen-2-ylmethyl)quinazolin-4-amineE
• CAS: 1225440-72-1
• 化学式: C₁₃H₁₀BrN₃S
• 分子量: 320.212
• InChiKey: JBFGMUSCBJSAOX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  66
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-bromo-N-(thiophen-2-ylmethyl)quinazolin-4-amine 、 3.4-(亚甲基二氧基)苯硼酸 在 四(三苯基膦)钯 sodium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以58%的产率得到ML 106
  参考文献：
  名称：

  [EN] QUINAZOLIN-4-AMINE DERIVATIVES; AND METHODS OF USE
  [FR] DÉRIVÉS DE LA QUINAZOLIN-4-AMINE; ET MÉTHODES D'UTILISATION

  摘要：

  本文公开了新型的喹唑啉-4-胺衍生物，它们是Clk1、Clk2、Clk3、Clk4或Dyrk1A的抑制剂。还公开了喹唑啉-4-胺衍生物作为Clk1、Clk4和Dyrk1A的有效和选择性抑制剂。这些药剂为研究Clk1、Clk4和Dyrk1A及其在前mRNA剪接中的作用提供了有用的工具。本文还公开了使用某些喹唑啉-4-胺衍生物治疗Clk1、Clk2、Clk4或Dyrk1A激酶介导的疾病的方法。

  公开号：

  WO2011041655A1
• 作为产物：
  描述：

  2-噻吩甲胺 、 6-溴-4-氯喹唑啉 在 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以99%的产率得到6-bromo-N-(thiophen-2-ylmethyl)quinazolin-4-amine
  参考文献：
  名称：

  [EN] QUINAZOLIN-4-AMINE DERIVATIVES; AND METHODS OF USE
  [FR] DÉRIVÉS DE LA QUINAZOLIN-4-AMINE; ET MÉTHODES D'UTILISATION

  摘要：

  本文公开了新型的喹唑啉-4-胺衍生物，它们是Clk1、Clk2、Clk3、Clk4或Dyrk1A的抑制剂。还公开了喹唑啉-4-胺衍生物作为Clk1、Clk4和Dyrk1A的有效和选择性抑制剂。这些药剂为研究Clk1、Clk4和Dyrk1A及其在前mRNA剪接中的作用提供了有用的工具。本文还公开了使用某些喹唑啉-4-胺衍生物治疗Clk1、Clk2、Clk4或Dyrk1A激酶介导的疾病的方法。

  公开号：

  WO2011041655A1

文献信息

• [EN] QUINAZOLIN-4-AMINE DERIVATIVES; AND METHODS OF USE<br/>[FR] DÉRIVÉS DE LA QUINAZOLIN-4-AMINE; ET MÉTHODES D'UTILISATION
  申请人：US HEALTH

  公开号：WO2011041655A1

  公开（公告）日：2011-04-07

  Disclosed herein are novel quinazolin-4-amine derivatives that are inhibitors of Clk1, Clk2, Clk3, Clk4, or Dyrk1A. Also disclosed are quinazolin-4-amine derivatives as potent and selective inhibitors of Clk1, Clk4, and Dyrk1A. These agents provide useful tools for the study of Clk1, Clk4 and Dyrk1A and their respective roles in pre-mRNA splicing. Methods of treating Clk1, Clk2, Clk4, or Dyrk1A kinase mediated disorders with certain quinazolin-4-amine derivatives are also disclosed.

  本文公开了新型的喹唑啉-4-胺衍生物，它们是Clk1、Clk2、Clk3、Clk4或Dyrk1A的抑制剂。还公开了喹唑啉-4-胺衍生物作为Clk1、Clk4和Dyrk1A的有效和选择性抑制剂。这些药剂为研究Clk1、Clk4和Dyrk1A及其在前mRNA剪接中的作用提供了有用的工具。本文还公开了使用某些喹唑啉-4-胺衍生物治疗Clk1、Clk2、Clk4或Dyrk1A激酶介导的疾病的方法。
• Fabrication of Furan-Functionalized Quinazoline Hybrids: Their Antibacterial Evaluation, Quantitative Proteomics, and Induced Phytopathogen Morphological Variation Studies
  作者：Qing-Su Long、Li-Wei Liu、Yong-Liang Zhao、Pei-Yi Wang、Biao Chen、Zhong Li、Song Yang

  DOI：10.1021/acs.jafc.9b03419

  日期：2019.10.9

  The limited number of agrochemicals targeting plant bacterial diseases has driven us to develop highly efficient, low-cost, and versatile antibacterial alternatives. Herein, a novel type of simple furan-functionalized quinazolin-4-amines was systematically fabricated and screened for their antibacterial activity. Bioassay results revealed that compounds C-1 and E-4 could substantially block the growth of two frequently mentioned pathogens Xanthomonas oryzae pv oryzae and X. axonopodis pv citri in vitro, displaying appreciable EC50 values of 7.13 and 10.3 mg/L, respectively. This effect was prominently improved by comparing those of mainly used agrochemicals. An in vivo experiment against bacterial blight further illustrated their viable applications as antimicrobial ingredients. Quantitative proteomics demonstrated that C-1 possessed a remarkable ability to manipulate the upregulation and downregulation of expressed proteins, which probably involved D-glucose and biotin metabolic pathways. This finding was substantially verified by parallel reaction monitoring analysis. Scanning electron microscopy images and fluorescence spectra also indicated that the designed compounds had versatile capacities for destroying the integrity of bacteria. Given these remarkable characteristics, furan-functionalized quinazoline hybrids can serve as a viable platform for developing innovative antibiotic alternatives against bacterial infections.
• Evaluation of substituted 6-arylquinazolin-4-amines as potent and selective inhibitors of cdc2-like kinases (Clk)
  作者：Bryan T. Mott、Cordelle Tanega、Min Shen、David J. Maloney、Paul Shinn、William Leister、Juan J. Marugan、James Inglese、Christopher P. Austin、Tom Misteli、Douglas S. Auld、Craig J. Thomas

  DOI：10.1016/j.bmcl.2009.09.121

  日期：2009.12

  A series of substituted 6-arylquinazolin-4-amines were prepared and analyzed as inhibitors of Clk4. Synthesis, structure-activity relationships and the selectivity of a potent analogue against a panel of 402 kinases are presented. Inhibition of Clk4 by these agents at varied concentrations of assay substrates (ATP and receptor peptide) highly suggests that this chemotype is an ATP competitive inhibitor. Molecular docking provides further evidence that inhibition is the result of binding at the kinase hinge region. Selected compounds represent novel tools capable of potent and selective inhibition of Clk1, Clk4, and Dyrk1A. Published by Elsevier Ltd.