methyl 2-(4-bromophenyl)-4-(dibromomethyl)thiazole-5-carboxylate | 1313711-70-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: methyl 2-(4-bromophenyl)-4-(dibromomethyl)thiazole-5-carboxylate
• 英文别名: Methyl 2-(4-bromophenyl)-4-(dibromomethyl)-1,3-thiazole-5-carboxylate
• CAS: 1313711-70-4
• 化学式: C₁₂H₈Br₃NO₂S
• 分子量: 469.979
• InChiKey: ANTWNQLAXOKONY-UHFFFAOYSA-N

物化性质

• 熔点：
  120-122 °C
• 沸点：
  503.5±60.0 °C(predicted)
• 密度：
  2.000±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  67.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  methyl 2-(4-bromophenyl)-4-methylthiazole-5-carboxylate 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 四氯化碳 为溶剂， 反应 6.0h， 以60%的产率得到methyl 2-(4-bromophenyl)-4-(dibromomethyl)thiazole-5-carboxylate
  参考文献：
  名称：

  An investigation of phenylthiazole antiflaviviral agents

  摘要：

  Flaviviruses are one of the most clinically important pathogens and their infection rates are increasing steadily. The phenylthiazole ring system has provided a template for the design and synthesis of antiviral agents that inhibit the flaviviruses by targeting their E-protein. Unfortunately, there is a correlation between phenylthiazole antiflaviviral activity and the presence of the reactive and therefore potentially toxic mono-or dibromomethyl moieties at thiazole-C4. Adding a linear hydrophobic tail para to the phenyl ring led to a new class of phenylthiazole antiflaviviral compounds that lack the toxic dibromomethyl moiety. This led to development of a drug-like phenylthiazole 12 that had high antiflaviviral selectivity (TI = 147). (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.04.041

文献信息

• An investigation of phenylthiazole antiflaviviral agents
  作者：Abdelrahman S. Mayhoub、Mansoora Khaliq、Carolyn Botting、Ze Li、Richard J. Kuhn、Mark Cushman

  DOI：10.1016/j.bmc.2011.04.041

  日期：2011.6

  Flaviviruses are one of the most clinically important pathogens and their infection rates are increasing steadily. The phenylthiazole ring system has provided a template for the design and synthesis of antiviral agents that inhibit the flaviviruses by targeting their E-protein. Unfortunately, there is a correlation between phenylthiazole antiflaviviral activity and the presence of the reactive and therefore potentially toxic mono-or dibromomethyl moieties at thiazole-C4. Adding a linear hydrophobic tail para to the phenyl ring led to a new class of phenylthiazole antiflaviviral compounds that lack the toxic dibromomethyl moiety. This led to development of a drug-like phenylthiazole 12 that had high antiflaviviral selectivity (TI = 147). (C) 2011 Elsevier Ltd. All rights reserved.