4-N-(4-chlorophenyl)-2,1,3-benzoxadiazole-4,7-diamine | 1154875-33-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶二唑类
• 英文名称: 4-N-(4-chlorophenyl)-2,1,3-benzoxadiazole-4,7-diamine
• CAS: 1154875-33-8
• 化学式: C₁₂H₉ClN₄O
• mdl: MFCD12425005
• 分子量: 260.683
• InChiKey: YTGLMZROJOCVBE-UHFFFAOYSA-N

物化性质

• 沸点：
  456.7±55.0 °C(predicted)
• 密度：
  1.506±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 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：
  77
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  N-(4-chlorophenyl)-7-nitrobenzo[c][1,2,5]oxadiazol-4-amine 在 盐酸 、 铁粉 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 1.0h， 以58%的产率得到4-N-(4-chlorophenyl)-2,1,3-benzoxadiazole-4,7-diamine
  参考文献：
  名称：

  Identification, synthesis and evaluation of substituted benzofurazans as inhibitors of CREB-mediated gene transcription

  摘要：

  Cyclic-AMP response-element binding protein (CREB) is a stimulus-activated transcription factor. Its transcription activity requires its binding with CREB-binding protein (CBP) after CREB is phosphorylated at Ser133. The domains involved for CREB-CBP interaction are kinase-inducible domain (KID) from CREB and KID-interacting domain (KIX) from CBP. Recent studies suggest that CREB is an attractive target for novel cancer therapeutics. To identify novel chemotypes as inhibitors of KIX-KID interaction, we screened the NCI-diversity set of compounds using a split renilla luciferase assay and identified 2-[(7-nitrobenzo[ c][1,2,5]oxadiazol-4-yl)thio] pyridine 1-oxide (compound 1, NSC228155) as a potent inhibitor of KIX-KID interaction. However, compound 1 was not particularly selective against CREB-mediated gene transcription in living HEK 293T cells. Further structure-activityrelationship studies identified 4-aniline substituted nitrobenzofurazans with improved selectivity. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.07.053

文献信息

• Identification, synthesis and evaluation of substituted benzofurazans as inhibitors of CREB-mediated gene transcription
  作者：Fuchun Xie、Bingbing X. Li、Candice Broussard、Xiangshu Xiao

  DOI：10.1016/j.bmcl.2013.07.053

  日期：2013.10

  Cyclic-AMP response-element binding protein (CREB) is a stimulus-activated transcription factor. Its transcription activity requires its binding with CREB-binding protein (CBP) after CREB is phosphorylated at Ser133. The domains involved for CREB-CBP interaction are kinase-inducible domain (KID) from CREB and KID-interacting domain (KIX) from CBP. Recent studies suggest that CREB is an attractive target for novel cancer therapeutics. To identify novel chemotypes as inhibitors of KIX-KID interaction, we screened the NCI-diversity set of compounds using a split renilla luciferase assay and identified 2-[(7-nitrobenzo[ c][1,2,5]oxadiazol-4-yl)thio] pyridine 1-oxide (compound 1, NSC228155) as a potent inhibitor of KIX-KID interaction. However, compound 1 was not particularly selective against CREB-mediated gene transcription in living HEK 293T cells. Further structure-activityrelationship studies identified 4-aniline substituted nitrobenzofurazans with improved selectivity. (C) 2013 Elsevier Ltd. All rights reserved.