3-(tert-butoxycarbonylamino)-N-(4-chlorophenyl)-2-naphthamide | 1373121-89-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-(tert-butoxycarbonylamino)-N-(4-chlorophenyl)-2-naphthamide
• 英文别名: tert-butyl N-[3-[(4-chlorophenyl)carbamoyl]naphthalen-2-yl]carbamate
• CAS: 1373121-89-1
• 化学式: C₂₂H₂₁ClN₂O₃
• 分子量: 396.873
• InChiKey: UOJGMKWZXLIRKK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  28
• 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：
  67.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(tert-butoxycarbonylamino)-N-(4-chlorophenyl)-2-naphthamide 在 盐酸 、 三氟乙酸 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 8.0h， 以69%的产率得到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
• 作为产物：
  描述：

  3-氨基-2-萘甲酸 在 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 、 水 、 乙腈 为溶剂， 反应 10.0h， 生成 3-(tert-butoxycarbonylamino)-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.