(4-Nitro-2,1,3-benzoxadiazol-7-yl)methanol | 1454663-35-4

• 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-Nitro-2,1,3-benzoxadiazol-7-yl)methanol
• 英文别名: (4-nitro-2,1,3-benzoxadiazol-7-yl)methanol
• CAS: 1454663-35-4
• 化学式: C₇H₅N₃O₄
• 分子量: 195.134
• InChiKey: RMUHSZULDDANER-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  105
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (4-Nitro-2,1,3-benzoxadiazol-7-yl)methanol 在 sodium chlorite 、 sodium dihydrogenphosphate 、 2-甲基-2-丁烯 、 甲基磺酰氯 、 三乙胺 、 2-碘酰基苯甲酸 作用下， 以 四氢呋喃 、 水 、 二甲基亚砜 、 正丁醇 为溶剂， 生成 N-(4-chlorophenyl)-4-nitro-2,1,3-benzoxadiazole-7-carboxamide
  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
• 作为产物：
  描述：

  2,1,3-苯并噁二唑-4-甲醇 在 硫酸 、 硝酸 作用下， 以36%的产率得到(4-Nitro-2,1,3-benzoxadiazol-7-yl)methanol
  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.