| 1589071-47-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• CAS: 1589071-47-5
• 化学式: C₁₂H₁₂Br₂O₂
• 分子量: 348.034
• InChiKey: ZRIQKNUVCQVNOF-JXMROGBWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.79
• 重原子数：
  16.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  、 2-巯基苯并恶唑 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 以89%的产率得到(Z)-ethyl 2-((benzo[d]oxazol-2-ylthio) methyl)-3-(4-bromophenyl)acrylate
  参考文献：
  名称：

  Synthesis of thio-heterocyclic analogues from Baylis–Hillman bromides as potent cyclooxygenase-2 inhibitors

  摘要：

  A series of thio-substituted pyrimidine, benzoxazole, benzothiazole and triazole analogues were synthesized from Baylis-Hillman bromides in a clean and efficient way. The synthesized twenty new compounds were subjected to in vitro COX-1 and COX-2 inhibitory activity. Majority of compounds found to be highly selective COX-2 inhibitor. Seven compounds (16e, 16f, 16k, 16l, 16m, 16r and 16s) displayed anti-inflammatory activity at micromolar concentrations with IC50 values for COX-2 inhibition ranging from 2.93 to 5.34 mu M compared to reference drug whose IC50 is 2.66 mu M. All these seven compounds had very little COX-1 inhibition property and thus are suitable candidates for anti-inflammatory drugs with less gastrointestinal side effect. (c) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.02.073
• 作为产物：
  描述：

  丙烯酸乙酯 在 三乙烯二胺 、 硫酸 、 氢溴酸 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Synthesis of thio-heterocyclic analogues from Baylis–Hillman bromides as potent cyclooxygenase-2 inhibitors

  摘要：

  A series of thio-substituted pyrimidine, benzoxazole, benzothiazole and triazole analogues were synthesized from Baylis-Hillman bromides in a clean and efficient way. The synthesized twenty new compounds were subjected to in vitro COX-1 and COX-2 inhibitory activity. Majority of compounds found to be highly selective COX-2 inhibitor. Seven compounds (16e, 16f, 16k, 16l, 16m, 16r and 16s) displayed anti-inflammatory activity at micromolar concentrations with IC50 values for COX-2 inhibition ranging from 2.93 to 5.34 mu M compared to reference drug whose IC50 is 2.66 mu M. All these seven compounds had very little COX-1 inhibition property and thus are suitable candidates for anti-inflammatory drugs with less gastrointestinal side effect. (c) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.02.073