4-[(2-Dimethylamino-ethylcarbamoyl)-methoxy]-naphthalene-1-carboxylic acid (3-fluoro-phenyl)-amide

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4-[(2-Dimethylamino-ethylcarbamoyl)-methoxy]-naphthalene-1-carboxylic acid (3-fluoro-phenyl)-amide
• 英文别名: 4-[2-[2-(dimethylamino)ethylamino]-2-oxoethoxy]-N-(3-fluorophenyl)naphthalene-1-carboxamide
• 化学式: C₂₃H₂₄FN₃O₃
• 分子量: 409.46
• InChiKey: AQPVMOZPQDRKDP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  70.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-甲氧基-1-萘甲酸 在 lithium hydroxide 、 三氯化铝 、 氯化亚砜 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 potassium carbonate 、 N,N-二异丙基乙胺 、 乙硫醇 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 13.5h， 生成 4-[(2-Dimethylamino-ethylcarbamoyl)-methoxy]-naphthalene-1-carboxylic acid (3-fluoro-phenyl)-amide
  参考文献：
  名称：

  Privileged scaffolds for blocking protein–protein interactions: 1,4-disubstituted naphthalene antagonists of transcription factor complex HOX–PBX/DNA

  摘要：

  Structure-based-design studies, with the crystal structure of the HOXB1-PBX1/DNA transcription factor complex, were used to identify 1,4-disubstituted naphthalenes as potential antagonists. An initial library of 32 analogs was synthesized, two of which were found to be more potent than the reported activity for a 12 amino acid peptide antagonist. Antagonists were also identified of the related BRN1/DNA and BRN2/DNA transcription factor complexes indicating that a 1,4-disubsituted naphthalene may be a privileged scaffold for preparing screening libraries targeting this family of transcription factor complexes. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.05.068

文献信息

• US7662750B2
  申请人：——

  公开号：US7662750B2

  公开（公告）日：2010-02-16
• Privileged scaffolds for blocking protein–protein interactions: 1,4-disubstituted naphthalene antagonists of transcription factor complex HOX–PBX/DNA
  作者：Tao Ji、Madison Lee、Steven C. Pruitt、David G. Hangauer

  DOI：10.1016/j.bmcl.2004.05.068

  日期：2004.8

  Structure-based-design studies, with the crystal structure of the HOXB1-PBX1/DNA transcription factor complex, were used to identify 1,4-disubstituted naphthalenes as potential antagonists. An initial library of 32 analogs was synthesized, two of which were found to be more potent than the reported activity for a 12 amino acid peptide antagonist. Antagonists were also identified of the related BRN1/DNA and BRN2/DNA transcription factor complexes indicating that a 1,4-disubsituted naphthalene may be a privileged scaffold for preparing screening libraries targeting this family of transcription factor complexes. (C) 2004 Elsevier Ltd. All rights reserved.