7-bromo-2-(4-nitro-phenyl)-benzo[d]imidazo[2,1-b]thiazole | 38956-39-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 7-bromo-2-(4-nitro-phenyl)-benzo[d]imidazo[2,1-b]thiazole
• 英文别名: 6-Bromo-2-(4-nitrophenyl)imidazo[2,1-b][1,3]benzothiazole
• CAS: 38956-39-7
• 化学式: C₁₅H₈BrN₃O₂S
• 分子量: 374.217
• InChiKey: UVPIZFJKFQYQKP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  91.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  7-bromo-2-(4-nitro-phenyl)-benzo[d]imidazo[2,1-b]thiazole 在 tin(II) chloride dihdyrate 作用下， 以 乙醇 为溶剂， 反应 4.0h， 生成 2-(4-aminophenyl)-7-bromoimidazo[2,1-b]benzothiazole
  参考文献：
  名称：

  2-Arylimidazo[2,1-b]benzothiazoles: A new family of amyloid binding agents with potential for PET and SPECT imaging of Alzheimer’s brain

  摘要：

  We designed and synthesized a small series of 2-aryl-imidazo[2,1-b]benzothiazole, representing a combination of motifs from the two most potent amyloid imaging agents, PIB and IMPY. The binding affinity of the new compounds ranged from 6 to 133 nM. Among the best compounds, 3b (K-i = 6 nM) can be labeled with (CH3)-C-11 for PET imaging whereas 3j (K-i = 10.9 nM) can be labeled with I-123 for SPECT imaging. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.03.052
• 作为产物：
  描述：

  2-氨基-6-溴苯并噻唑 、 2-溴-4'-硝基苯乙酮 以 乙醇 为溶剂， 反应 18.0h， 生成 7-bromo-2-(4-nitro-phenyl)-benzo[d]imidazo[2,1-b]thiazole
  参考文献：
  名称：

  Investigations in the imidazole series

  摘要：

  DOI：

  10.1007/bf00944233

文献信息

• Identification of new aminoacid amides containing the imidazo[2,1-b]benzothiazol-2-ylphenyl moiety as inhibitors of tumorigenesis by oncogenic Met signaling
  作者：Alessandro Furlan、Francesco Colombo、Andrea Kover、Nathalie Issaly、Cristina Tintori、Lucilla Angeli、Vincent Leroux、Sébastien Letard、Mercedes Amat、Yasmine Asses、Bernard Maigret、Patrice Dubreuil、Maurizio Botta、Rosanna Dono、Joan Bosch、Oreste Piccolo、Daniele Passarella、Flavio Maina

  DOI：10.1016/j.ejmech.2011.10.051

  日期：2012.1

  The Met receptor tyrosine kinase is a promising target in anticancer therapies for its role during tumor evolution and resistance to treatment. It is characterized by an unusual structural plasticity as its active site accepts different inhibitor binding modes. Such feature can be exploited to identify distinct agents targeting tumor dependence and/or resistance by oncogenic Met. Here we report the identification of bioactive agents, featuring a new 4-(imidazo[2,1-b]benzothiazol-2-yl)phenyl moiety, targeting cancer cells dependent on oncogenic Met. One of these compounds (7c; Triflorcas) impairs survival, anchorage-independent growth, and in vivo tumorigenesis, without showing side effects. Our medicinal chemistry strategy was based on an in-house Met-focused library of aminoacid-amide derivatives enriched through structure-based computer modeling, taking into account the Met multiple-binding-mode feature. Altogether, our findings show how a rational structure-based drug design approach coupled to cell-based drug evaluation strategies can be applied in medicinal chemistry to identify new agents targeting a given oncogenic-dependency setting. (C) 2011 Elsevier Masson SAS. All rights reserved.