N-(3-methyl-4-phenylthiazol-2(3H)-ylidene)furan-2-carboxamide | 1120313-02-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃
• 英文名称: N-(3-methyl-4-phenylthiazol-2(3H)-ylidene)furan-2-carboxamide
• 英文别名: N-(3-methyl-4-phenyl-1,3-thiazol-2-ylidene)furan-2-carboxamide
• CAS: 1120313-02-1
• 化学式: C₁₅H₁₂N₂O₂S
• 分子量: 284.338
• InChiKey: IJXMZSVJHOZOCO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-异硫氰酸呋喃酯 在 溶剂黄146 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 N-(3-methyl-4-phenylthiazol-2(3H)-ylidene)furan-2-carboxamide
  参考文献：
  名称：

  Synthesis of 2-amino-5-benzoyl-4-(2-furyl)thiazoles as adenosine A2A receptor antagonists

  摘要：

  The discovery and synthesis of a series of 2-amino-5-benzoyl-4-(2-furyl)thiazoles as adenosine A(2A) receptor antagonists from a small-molecule combinatorial library using a high-throughput radioligand-binding assay is described. Antagonists were further characterized in the A(2A) binding assay and an A(1) selectivity assay. Selected examples exhibited excellent affinity for A(2A) and good selectivity versus the A(1) receptor. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.11.066

文献信息

• Discovery of a Series of Thiazole Derivatives as Novel Inhibitors of Metastatic Cancer Cell Migration and Invasion
  作者：Shilong Zheng、Qiu Zhong、Quan Jiang、Madhusoodanan Mottamal、Qiang Zhang、Naijue Zhu、Matthew E. Burow、Rebecca A. Worthylake、Guangdi Wang

  DOI：10.1021/ml300322n

  日期：2013.2.14

  Effective inhibitors of cancer cell migration and invasion can potentially lead to clinical applications as therapy to block tumor metastasis, the primary cause of death in cancer patients. To this end we have designed and synthesized a series of thiazole derivatives that showed potent efficacy against cell migration and invasion in metastatic cancer cells. The most effective compound, 5k, was found

  癌细胞迁移和侵袭的有效抑制剂有可能导致临床应用作为阻断肿瘤转移的疗法，而肿瘤转移是癌症患者死亡的主要原因。为此，我们设计并合成了一系列噻唑衍生物，它们在转移癌细胞中显示出有效的抗细胞迁移和侵袭能力。在MDA-MB-231细胞的剂量依赖性跨孔迁移测定中，发现最有效的化合物5k的IC50值为176 nM。在10μM的剂量下，5k还阻止了HeLa和A549细胞中约80％的迁移以及MDA-MB-231细胞中60％的侵袭。重要的是，大多数衍生物在克隆形成测定中没有表现出明显的细胞毒性。这些抗迁移衍生物的低至微不足道的细胞增殖抑制作用是其理想的性能，因为它们有望对作为潜在治疗剂的健康细胞具有低毒性。通过显微镜分析肌动蛋白细胞骨架的机理研究表明，化合物5k大大减少了细胞内的肌动蛋白，并阻止了fascin定位于富含肌动蛋白的膜突起。这些结果表明，抗迁移活性可能是由驱动迁移所必需的突起中的肌动蛋白结构受损引起的。
• Synthesis of 2-amino-5-benzoyl-4-(2-furyl)thiazoles as adenosine A2A receptor antagonists
  作者：Andrew G. Cole、Tara M. Stauffer、Laura L. Rokosz、Axel Metzger、Lawrence W. Dillard、Wenguang Zeng、Ian Henderson

  DOI：10.1016/j.bmcl.2008.11.066

  日期：2009.1

  The discovery and synthesis of a series of 2-amino-5-benzoyl-4-(2-furyl)thiazoles as adenosine A(2A) receptor antagonists from a small-molecule combinatorial library using a high-throughput radioligand-binding assay is described. Antagonists were further characterized in the A(2A) binding assay and an A(1) selectivity assay. Selected examples exhibited excellent affinity for A(2A) and good selectivity versus the A(1) receptor. (C) 2008 Elsevier Ltd. All rights reserved.