(E)-N-(benzofuran-3-ylmethyl)-3-(furan-2-yl)-N-methylprop-2-en-1-amine hydrochloride

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: (E)-N-(benzofuran-3-ylmethyl)-3-(furan-2-yl)-N-methylprop-2-en-1-amine hydrochloride
• 英文别名: (E)-N-methyl-N-[(furan-3-yl)methylene]-3-(furan-2-yl)prop-2-en-1-amine hydrochloride；(E)-N-(1-benzofuran-3-ylmethyl)-3-(furan-2-yl)-N-methylprop-2-en-1-amine;hydrochloride
• 化学式: C₁₇H₁₇NO₂*ClH
• 分子量: 303.788
• InChiKey: IUKHOKYBZNRKHO-CVDVRWGVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.59
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  反-3-(2-呋喃基)丙烯醛 在 sodium tetrahydroborate 、 三溴化磷 、 potassium carbonate 作用下， 以 甲醇 、 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.77h， 生成 (E)-N-(benzofuran-3-ylmethyl)-3-(furan-2-yl)-N-methylprop-2-en-1-amine hydrochloride
  参考文献：
  名称：

  Novel Terminal Bipheny-Based Diapophytoene Desaturases (CrtN) Inhibitors as Anti-MRSA/VISR/LRSA Agents with Reduced hERG Activity

  摘要：

  CrtN has been identified as an attractive and druggable target for treating pigmented Staphylococcus aureus infections. More than 100 new compounds were synthesized, which target the overwhelming the defects of the CrtN inhibitor 1. Analogues 23a and 23b demonstrated a significant activity against pigmented S. aureus Newman and 13 MRSA strains (IC50 = 0.02-10.5 nM), along with lower hERG inhibition (IC50 > 30 mu M, similar to 10-fold decrease in comparison with 1). Furthermore, 23a and 23b were confirmed to reduce the staphylococcal load in the kidney and heart in a mouse model with normal treatment deeper than pretreatment ones, comparable even with vancomycin and linezolid. Remarkably, 23a could strongly block the pigment biosynthesis of these nine multidrug-resistant MRSA strains, including excellent activity against LRSA strains and VISA strains in vivo, and all of which demonstrated that 23a has a huge potential against intractable MRSA, VISA, and LRSA issues as a therapeutic drug.

  DOI：

  10.1021/acs.jmedchem.7b01300