6-(4-fluorophenyl)-2-methylimidazo[2,1-b]thiazol-5-carbaldehyde | 139389-29-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 6-(4-fluorophenyl)-2-methylimidazo[2,1-b]thiazol-5-carbaldehyde
• 英文别名: 6-(4-Fluorophenyl)-2-methylimidazo[2,1-b]thiazole-5-carbaldehyde；6-(4-fluorophenyl)-2-methylimidazo[2,1-b][1,3]thiazole-5-carbaldehyde
• CAS: 139389-29-0
• 化学式: C₁₃H₉FN₂OS
• 分子量: 260.292
• InChiKey: WAGPRQNGIYQHQA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  62.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-(4-fluorophenyl)-2-methylimidazo[2,1-b]thiazol-5-carbaldehyde 、 肼甲酰亚胺酰胺一氯化氢 以 乙醇 为溶剂， 生成 NSC 747107
  参考文献：
  名称：

  Imidazo[2,1-b]thiazole guanylhydrazones as RSK2 inhibitors

  摘要：

  The activity of a series of imidazo[2,1-b]thiazole guanylhydrazones as inhibitors of p90 ribosomal S6 kinase 2 (RSK2) is described. It was found that a small subset of compounds show both potent inhibition of RSK2 kinase activity and tumor cell growth in vitro. Detailed study of one of the most active compounds indicates a high degree of selectivity for inhibition of RSK2 compared to a spectrum of other related kinases. Selective inhibition of the MCF-7 breast tumor cell line compared to MCF-10A non-transformed cells, as well as selective inhibition of the biomarker GSK3 provides evidence that the compounds can affect the RSK2 target in cells. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.07.001
• 作为产物：
  描述：

  2-溴-4'-氟苯乙酮 在 盐酸 、 三氯氧磷 作用下， 以 氯仿 、 水 、 丙酮 为溶剂， 反应 1.0h， 生成 6-(4-fluorophenyl)-2-methylimidazo[2,1-b]thiazol-5-carbaldehyde
  参考文献：
  名称：

  咪唑并噻唑-查尔酮衍生物的合成作为抗癌和凋亡诱导剂

  摘要：

  合成了新型的咪唑并[2,1– b ]噻唑查尔酮衍生物，并对其抗癌活性进行了评估。这些查耳酮衍生物显示出令人鼓舞的活性，log GI 50值为-7.51至-4.00。研究了这些衍生物对MCF-7细胞系的详细生物学特性。有趣的是，这些查耳酮衍生物诱导了G 0 / G 1期细胞周期停滞，下调了G 1。细胞周期调节蛋白，如细胞周期蛋白D1和细胞周期蛋白E1，以及CDK4的上调。此外，这些化合物还引发了细胞凋亡的特征性特征，例如p53，p21和p27水平的升高，NF-κB的抑制以及caspase-9的上调。这些查耳酮衍生物之一3 d可能非常适合单独或与现有疗法组合进行详细的生物学研究。

  DOI：

  10.1002/cmdc.201000346

文献信息

• 4-Imidazo[2,1-b]thiazole-1,4-DHPs and neuroprotection: preliminary study in hits searching
  作者：Alberto Leoni、Maria Frosini、Alessandra Locatelli、Matteo Micucci、Claudio Carotenuto、Miriam Durante、Sandro Cosconati、Roberta Budriesi

  DOI：10.1016/j.ejmech.2019.02.075

  日期：2019.5

  particular the strategy adopted for designing the compounds involves the imidazo[2,1-b]thiazole nucleus. The observed properties show that substituents at C2 and C6 of the bicyclic scaffold are able to influence the cardiovascular parameters and the neuroprotective activity. In comparison to nifedipine, a set of derivatives such as compound 6, showed a neuroprotective profile of particular interest.

  在目前的工作中，我们描述了4-咪唑并[2,1 - b ]噻唑-1,4-二氢吡啶类重点文库的合成，表征和神经保护作用的评估。此外，在心脏组织和血管平滑肌中对新的二氢吡啶进行了功能性体外测定，以确定它们在抵消神经退行性变中的可能选择性。特别是，设计化合物所采用的策略涉及咪唑并[2,1- b ]噻唑核。观察到的性质表明，双环支架的C2和C6处的取代基能够影响心血管参数和神经保护活性。与硝苯地平相比，一组衍生物如化合物6表现出特别重要的神经保护作用。
• Imidazo[2,1-b]thiazole guanylhydrazones as RSK2 inhibitors
  作者：Aldo Andreani、Massimiliano Granaiola、Alberto Leoni、Alessandra Locatelli、Rita Morigi、Mirella Rambaldi、Lucilla Varoli、Deborah Lannigan、Jeff Smith、Dominic Scudiero、Sudhir Kondapaka、Robert H. Shoemaker

  DOI：10.1016/j.ejmech.2011.07.001

  日期：2011.9

  The activity of a series of imidazo[2,1-b]thiazole guanylhydrazones as inhibitors of p90 ribosomal S6 kinase 2 (RSK2) is described. It was found that a small subset of compounds show both potent inhibition of RSK2 kinase activity and tumor cell growth in vitro. Detailed study of one of the most active compounds indicates a high degree of selectivity for inhibition of RSK2 compared to a spectrum of other related kinases. Selective inhibition of the MCF-7 breast tumor cell line compared to MCF-10A non-transformed cells, as well as selective inhibition of the biomarker GSK3 provides evidence that the compounds can affect the RSK2 target in cells. (C) 2011 Elsevier Masson SAS. All rights reserved.
• Synthesis of Imidazothiazole-Chalcone Derivatives as Anticancer and Apoptosis Inducing Agents
  作者：Ahmed Kamal、D. Dastagiri、M. Janaki Ramaiah、J. Surendranadha Reddy、E. Vijaya Bharathi、Chatla Srinivas、S. N. C. V. L. Pushpavalli、Dhananjaya Pal、Manika Pal-Bhadra

  DOI：10.1002/cmdc.201000346

  日期：2010.11.8

  class of imidazo[2,1‐b]thiazole chalcone derivatives were synthesized and evaluated for their anticancer activity. These chalcone derivatives show promising activity, with log GI50 values ranging from −7.51 to −4.00. The detailed biological aspects of these derivatives toward the MCF‐7 cell line were studied. Interestingly, these chalcone derivatives induced G0/G1‐phase cell‐cycle arrest, down‐regulation

  合成了新型的咪唑并[2,1– b ]噻唑查尔酮衍生物，并对其抗癌活性进行了评估。这些查耳酮衍生物显示出令人鼓舞的活性，log GI 50值为-7.51至-4.00。研究了这些衍生物对MCF-7细胞系的详细生物学特性。有趣的是，这些查耳酮衍生物诱导了G 0 / G 1期细胞周期停滞，下调了G 1。细胞周期调节蛋白，如细胞周期蛋白D1和细胞周期蛋白E1，以及CDK4的上调。此外，这些化合物还引发了细胞凋亡的特征性特征，例如p53，p21和p27水平的升高，NF-κB的抑制以及caspase-9的上调。这些查耳酮衍生物之一3 d可能非常适合单独或与现有疗法组合进行详细的生物学研究。