4-Carboxy-7-nitro-benzo-2,1,3-oxadiazol | 32863-22-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-Carboxy-7-nitro-benzo-2,1,3-oxadiazol
• 英文别名: 7-nitro-benzo[1,2,5]oxadiazole-4-carboxylic acid；7-Nitrobenzo[c][1,2,5]oxadiazole-4-carboxylic acid；4-nitro-2,1,3-benzoxadiazole-7-carboxylic acid
• CAS: 32863-22-2
• 化学式: C₇H₃N₃O₅
• 分子量: 209.118
• InChiKey: YIJGFZBRSHZSJB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  122
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  对氯苯胺 、 4-Carboxy-7-nitro-benzo-2,1,3-oxadiazol 在 甲基磺酰氯 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 以41%的产率得到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：

  苯并二唑-4-甲醛 在 sodium chlorite 、 sodium tetrahydroborate 、 sodium dihydrogenphosphate 、 2-甲基-2-丁烯 、 硫酸 、 硝酸 、 2-碘酰基苯甲酸 作用下， 以 四氢呋喃 、 甲醇 、 水 、 二甲基亚砜 、 正丁醇 为溶剂， 生成 4-Carboxy-7-nitro-benzo-2,1,3-oxadiazol
  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

• Mitochondria-Targeted Antioxidant Prodrugs and Methods of Use
  申请人：Anders Marion W.

  公开号：US20090306125A1

  公开（公告）日：2009-12-10

  The present invention is a mitochondria-targeted antioxidant prodrug useful for the prevention or treatment of diseases or conditions associated with mitochondrial dysfunction resulting from changes in the mitochondrial redox environment. Antioxidant prodrugs of the invention are produced by modifying an antioxidant to a fatty acid so that the resulting prodrug is targeted to and activated by an enzyme of mitochondrial fatty acid beta-oxidation.

  本发明是一种线粒体定位的抗氧化剂前药，可用于预防或治疗与线粒体氧化还原环境变化导致的线粒体功能障碍相关的疾病或病症。本发明的抗氧化剂前药通过将抗氧化剂修饰为脂肪酸，使得得到的前药能够定位并被线粒体脂肪酸β-氧化酶激活。
• Mitochondria-targeted antioxidant prodrugs and methods of use
  申请人：Anders Marion W.

  公开号：US20100168198A1

  公开（公告）日：2010-07-01

  The present invention is a mitochondria-targeted antioxidant prodrug useful for the prevention or treatment of diseases or conditions associated with mitochondrial dysfunction resulting from changes in the mitochondrial redox environment. Antioxidant prodrugs of the invention are produced by modifying an antioxidant to a fatty acid so that the resulting prodrug is targeted to and activated by an enzyme of mitochondrial fatty acid beta-oxidation.

  本发明是一种线粒体靶向抗氧化剂前药，用于预防或治疗与线粒体氧化还原环境变化导致的线粒体功能障碍有关的疾病或病症。该发明的抗氧化剂前药是通过将抗氧化剂改性为脂肪酸而产生的，从而使得产生的前药能够靶向并被线粒体脂肪酸β-氧化酶激活。
• MITOCHONDRIA-TARGETED ANTIOXIDANT PRODRUGS AND METHODS OF USE
  申请人：University of Rochester

  公开号：EP1954322A2

  公开（公告）日：2008-08-13
• US7470797B2
  申请人：——

  公开号：US7470797B2

  公开（公告）日：2008-12-30
• US7517904B2
  申请人：——

  公开号：US7517904B2

  公开（公告）日：2009-04-14