2-(7-nitrobenzo[c][1.2.5]oxadiazol-4-yl)thiopyridine | 1454663-34-3

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2-(7-nitrobenzo[c][1.2.5]oxadiazol-4-yl)thiopyridine
• 英文别名: 7-Nitro-4-pyridin-2-ylsulfanyl-2,1,3-benzoxadiazole；7-nitro-4-pyridin-2-ylsulfanyl-2,1,3-benzoxadiazole
• CAS: 1454663-34-3
• 化学式: C₁₁H₆N₄O₃S
• 分子量: 274.26
• InChiKey: SMYMEULFDMZQLS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  19
• 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：
  123
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  2-[(7-nitrobenzo[c][1,2,5]oxadiazol-4-yl)thio]pyridine 1-oxide 在 二甲氨基硫代甲酰氯 作用下， 以 乙腈 为溶剂， 以29%的产率得到2-(7-nitrobenzo[c][1.2.5]oxadiazol-4-yl)thiopyridine
  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

• Bem, Marioara; Radutiu, Ana Cristina; Voicescu, Mariana, Revue Roumaine de Chimie, 2018, vol. 63, # 2, p. 149 - 155
  作者：Bem, Marioara、Radutiu, Ana Cristina、Voicescu, Mariana、Caproiu, Miron T.、Draghici, Constantin、Maganu, Maria、Enache, Cristian、Constantinescu, Titus、Balaban, Alexandru T.

  DOI：——

  日期：——
• 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.