6-Chloro-N-(2-furanylmethyl)-4-quinazolinamine | 70128-50-6

• 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-Chloro-N-(2-furanylmethyl)-4-quinazolinamine
• 英文别名: 6-chloro-N-(furan-2-ylmethyl)quinazolin-4-amine
• CAS: 70128-50-6
• 化学式: C₁₃H₁₀ClN₃O
• 分子量: 259.695
• InChiKey: RZCANXWOLVJKFQ-UHFFFAOYSA-N

物化性质

• 沸点：
  422.3±40.0 °C(Predicted)
• 密度：
  1.404±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(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：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  51
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-Chloro-N-(2-furanylmethyl)-4-quinazolinamine 、 碘甲烷 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成
  参考文献：
  名称：

  Fabrication of Furan-Functionalized Quinazoline Hybrids: Their Antibacterial Evaluation, Quantitative Proteomics, and Induced Phytopathogen Morphological Variation Studies

  摘要：

  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.

  DOI：

  10.1021/acs.jafc.9b03419
• 作为产物：
  描述：

  4,6-二氯喹唑啉 、 2-呋喃甲胺 在 三乙胺 作用下， 以 异丙醇 为溶剂， 反应 1.0h， 生成 6-Chloro-N-(2-furanylmethyl)-4-quinazolinamine
  参考文献：
  名称：

  Fabrication of Furan-Functionalized Quinazoline Hybrids: Their Antibacterial Evaluation, Quantitative Proteomics, and Induced Phytopathogen Morphological Variation Studies

  摘要：

  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.

  DOI：

  10.1021/acs.jafc.9b03419

文献信息

• Potent Small Molecule Inhibitors of Autophagy, and Methods of Use Thereof
  申请人：Yuan Junying

  公开号：US20120258975A1

  公开（公告）日：2012-10-11

  Certain aspects of the invention relates to small molecule autophagy inhibitors of the formula (I), and their use for treatment and prevention of cancers and acute pancreatitis. As disclosed herein, a small molecule inhibitor of autophagy was been identified from an image-based screen in a known bioactive library. It was found that this autophagy inhibitor functions by promoting the degradation of type III PI3 kinase complex which is required for initiating autophagy. Medicinal chemistry studies led to small molecular autophagy inhibitors with improved potency and selectivity. (I)
• 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.