N-(6-fluorobenzo[d]thiazol-2-yl)benzamide | 16194-65-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: N-(6-fluorobenzo[d]thiazol-2-yl)benzamide
• 英文别名: N-(6-fluorobenzothiazol-2-yl)benzamide；N-(6-fluoro-benzothiazol-2-yl)-benzamide；N-Benzoyl-2-amino-6-fluor-benzthioazol；6-Fluor-2-benzamino-benzthiazol；N-(6-fluoro-1,3-benzothiazol-2-yl)benzamide
• CAS: 16194-65-3
• 化学式: C₁₄H₉FN₂OS
• 分子量: 272.303
• InChiKey: GPAIMYGNLZYSRN-UHFFFAOYSA-N

物化性质

• 密度：
  1.438±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 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：
  70.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  在 1,10-菲罗啉 、 copper(ll) sulfate pentahydrate 、 potassium carbonate 作用下， 以 二甲基亚砜 为溶剂， 反应 14.0h， 以82%的产率得到N-(6-fluorobenzo[d]thiazol-2-yl)benzamide
  参考文献：
  名称：

  铜促进的CS和CN交叉偶联反应：2-（N -Aryolamino）苯并噻唑和2-（N -Aryolamino）苯并咪唑的合成

  摘要：

  2-（N-芳基氨基）苯并噻唑和2-（N-芳基氨基）苯并咪唑的合成已在铜催化剂的存在下完成。这些反应涉及CS和CN交叉偶联反应。所有给电子和吸电子的取代基都容易进行反应，从而以良好或优异的产率得到目标产物。另外，该反应还以高产率批量生产目标产物。

  DOI：

  10.1016/j.tet.2019.05.006

文献信息

• On Water: Metal-Free Synthesis of Highly Functionalized Benzothiazolylidene from <i>ortho</i>-Haloanilines
  作者：Kapil Mohan Saini、Rakesh K. Saunthwal、Shiv Kumar、Akhilesh K. Verma

  DOI：10.1021/acs.joc.8b03107

  日期：2019.3.1

  An environmentally benign, transition-metal-free organic base promoted one-pot cascade synthesis of highly functionalized benzo[d]thiazol-2(3H)-ylidene benzamide in the presence of water was accomplished by three-component reaction of ortho-iodoanilines, acrylates, and aroyl isothiocyanates. The protocol involves the in situ generation of thiourea intermediate followed by triethylamine induced intramolecular

  通过邻位碘代苯胺的三组分反应，完成了在水存在下环境友好，无过渡金属的有机碱促进一锅级联合成高官能度的苯并[ d ]噻唑-2（3 H）-亚烷基苯甲酰胺。 ，丙烯酸酯和芳基异硫氰酸酯。该方案涉及原位生成硫脲中间体，然后三乙胺诱导的分子内SN Ar置换反应，随后将迈克尔加成到丙烯酸酯上，导致形成苯并[ d ]噻唑-2（3 H）-亚烷基苯甲酰胺。苯并[ b还可以使用酰胺化和分子内芳族亲核取代化学方法以高收率生成噻唑。控制实验支持所提出的机制途径。进一步的X射线晶体学研究证实了稠合的苯甲酰胺的指定结构。
• Identification of small-molecule inhibitors of the Aβ–ABAD interaction
  作者：Yuli Xie、Shixian Deng、Zhenzhang Chen、Shidu Yan、Donald W. Landry

  DOI：10.1016/j.bmcl.2006.05.099

  日期：2006.9

  The interaction of amyloid beta peptide (A beta) and A beta-binding alcohol dehydrogenase (ABAD) was recently implicated in the pathogenesis of Alzheimer's disease (AD). Using an ELISA-based screening assay, we identified frentizole, an FDA-approved immunosuppressive drug, as a novel inhibitor of the A beta-ABAD interaction. Analysis of the frentizole structure-activity relationship led to identification of a novel benzothiazole urea with a 30-fold improvement in potency. (c) 2006 Elsevier Ltd. All rights reserved.
• Benzothiazole-Based LRRK2 Inhibitors as Wnt Enhancers and Promoters of Oligodendrocytic Fate
  作者：Josefa Zaldivar-Diez、Lingling Li、Ana M. Garcia、Wen-Ning Zhao、Cristina Medina-Menendez、Stephen. J. Haggarty、Carmen Gil、Aixa V. Morales、Ana Martinez

  DOI：10.1021/acs.jmedchem.9b01752

  日期：2020.3.12

  Leucine rich repeat kinase 2 (LRRK2) is an enigmatic enzyme and a relevant target for Parkinson's disease (PD). However, despite the significant amount of research done in the past decade, the precise function of LRRK2 remains largely unknown. Moreover, the therapeutic potential of its inhibitors is in its infancy with the first clinical trial having just started. In the present work, the molecular mechanism of LRRK2 in the control of neurogenesis or gliogenesis was investigated. We designed and synthesized novel benzothiazole-based LRRK2 inhibitors and showed that they can modulate the Wnt/beta-catenin signaling pathway. Furthermore, compounds 5 and 14 were able to promote neural progenitors proliferation and drive their differentiation toward neuronal and oligodendrocytic cell fates. These results suggest potential new avenues for the application of LRRK2 inhibitors in demyelinating diseases in which oligodendrocyte cell-death is one of the pathological features.