2-(3-bromophenyl)-4-phenylthiazole | 2227-74-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-(3-bromophenyl)-4-phenylthiazole
• 英文别名: 2-m-Bromophenyl-4-phenylthiazol；2-m-Bromophenyl-4-phenyl-thiazoll；2-(3-Bromophenyl)-4-phenyl-1,3-thiazole；2-(3-bromophenyl)-4-phenyl-1,3-thiazole
• CAS: 2227-74-9
• 化学式: C₁₅H₁₀BrNS
• mdl: MFCD16617725
• 分子量: 316.221
• InChiKey: DSZFUGCHOLVVRX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  41.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  C₁₅H₁₀BrNO₂ 在 劳森试剂 作用下， 以 氯苯 为溶剂， 以62 %的产率得到2-(3-bromophenyl)-4-phenylthiazole
  参考文献：
  名称：

  Lawesson 试剂促进吖内酯脱氧合成 2,4-二取代噻唑

  摘要：

  吖内酯和噻唑是常见的结构基序，具有多种应用。开发了一种从吖内酯高效直接合成 2,4-二取代噻唑的新方法。在没有金属或外部添加剂的情况下，通过Lawesson 试剂对二氢唑酮进行脱氧来进行反应。合成了多种 2,4-二取代噻唑，收率高达 92%。此外，克级合成也证明了这种方法的重要性。

  DOI：

  10.1039/d2ob01939f

文献信息

• Optimization of thiazole analogues of resveratrol for induction of NAD(P)H:quinone reductase 1 (QR1)
  作者：Abdelrahman S. Mayhoub、Laura Marler、Tamara P. Kondratyuk、Eun-Jung Park、John M. Pezzuto、Mark Cushman

  DOI：10.1016/j.bmc.2012.10.006

  日期：2012.12

  NAD(P)H:quinone reductase 1 (QR1) belongs to a class of enzymes called cytoprotective enzymes. It exhibits its cancer protective activity mainly by inhibiting the formation of intracellular semiquinone radicals, and by generating alpha-tocopherolhydroquinone, which acts as a free radical scavenger. It is therefore believed that QR1 inducers can act as cancer chemopreventive agents. Resveratrol (1) is a naturally occurring stilbene derivative that requires a concentration of 21 mu M to double QR1 activity (CD = 21 mu M). The stilbene double bond of resveratrol was replaced with a thiadiazole ring and the phenols were eliminated to provide a more potent and selective derivative 2 (CD = 2.1 mu M). Optimizing the substitution pattern of the two phenyl rings and the central heterocyclic linker led to a highly potent and selective QR1 inducer 9o with a CD value of 0.087 mu M. (C) 2012 Elsevier Ltd. All rights reserved.
• US9966540B2
  申请人：——

  公开号：US9966540B2

  公开（公告）日：2018-05-08
• Lawesson's reagent promoted deoxygenation of azlactones for the syntheses of 2,4-disubstituted thiazoles
  作者：Gaofeng Yin、Xiaodong Wang、Yuqing Wang、Tao Shi、Yaofu Zeng、Yuying Wang、Xue Peng、Zhen Wang

  DOI：10.1039/d2ob01939f

  日期：——

  Azlactones and thiazoles are common structural motifs and possess diverse applications. A new method for the efficient and straightforward syntheses of 2,4-disubstituted thiazoles from azlactones has been developed. The reaction proceeded via deoxygenation of azlactones by Lawesson's reagent without metal or external additives. A variety of 2,4-disubstituted thiazoles were synthesized with up to 92%

  吖内酯和噻唑是常见的结构基序，具有多种应用。开发了一种从吖内酯高效直接合成 2,4-二取代噻唑的新方法。在没有金属或外部添加剂的情况下，通过Lawesson 试剂对二氢唑酮进行脱氧来进行反应。合成了多种 2,4-二取代噻唑，收率高达 92%。此外，克级合成也证明了这种方法的重要性。