3-amino-N-(4-chlorophenyl)-2-naphthamide | 1027576-25-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-amino-N-(4-chlorophenyl)-2-naphthamide
• 英文别名: 3-amino-N-(4-chlorophenyl)naphthalene-2-carboxamide
• CAS: 1027576-25-5
• 化学式: C₁₇H₁₃ClN₂O
• 分子量: 296.756
• InChiKey: UQVHMDMRYQDJOP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  55.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  三光气 、 3-amino-N-(4-chlorophenyl)-2-naphthamide 以 四氢呋喃 为溶剂， 反应 2.0h， 以69%的产率得到3-(4-chlorophenyl)benzo[g]quinazoline-2,4-(1H,3H)-dione
  参考文献：
  名称：

  Design, Synthesis, and Biological Evaluation of Conformationally Constrained Analogues of Naphthol AS-E as Inhibitors of CREB-Mediated Gene Transcription

  摘要：

  Cyclic AMP response element binding protein (CREB) is often dysregulated in cancer cells and is an attractive cancer drug target. Previously, we described naphthol AS-E (1) as a small molecule inhibitor of CREB-mediated gene transcription. To understand its bioactive conformation, a series of conformationally constrained analogues of 1 were designed and synthesized. Biological evaluation of these analogues suggests that the global energy minimum of 1 is the likely bioactive conformation.

  DOI：

  10.1021/jm300043c
• 作为产物：
  描述：

  3-氨基-2-萘甲酸 在 盐酸 、 potassium carbonate 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 1,4-二氧六环 、 乙醚 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 18.0h， 生成 3-amino-N-(4-chlorophenyl)-2-naphthamide
  参考文献：
  名称：

  Design, Synthesis, and Biological Evaluation of Conformationally Constrained Analogues of Naphthol AS-E as Inhibitors of CREB-Mediated Gene Transcription

  摘要：

  Cyclic AMP response element binding protein (CREB) is often dysregulated in cancer cells and is an attractive cancer drug target. Previously, we described naphthol AS-E (1) as a small molecule inhibitor of CREB-mediated gene transcription. To understand its bioactive conformation, a series of conformationally constrained analogues of 1 were designed and synthesized. Biological evaluation of these analogues suggests that the global energy minimum of 1 is the likely bioactive conformation.

  DOI：

  10.1021/jm300043c

文献信息

• Design, Synthesis, and Biological Evaluation of Conformationally Constrained Analogues of Naphthol AS-E as Inhibitors of CREB-Mediated Gene Transcription
  作者：Min Jiang、Bingbing X. Li、Fuchun Xie、Frances Delaney、Xiangshu Xiao

  DOI：10.1021/jm300043c

  日期：2012.4.26

  Cyclic AMP response element binding protein (CREB) is often dysregulated in cancer cells and is an attractive cancer drug target. Previously, we described naphthol AS-E (1) as a small molecule inhibitor of CREB-mediated gene transcription. To understand its bioactive conformation, a series of conformationally constrained analogues of 1 were designed and synthesized. Biological evaluation of these analogues suggests that the global energy minimum of 1 is the likely bioactive conformation.