| 215124-13-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• CAS: 215124-13-3
• 化学式: C₁₅H₉F₉O₆S
• 分子量: 488.284
• InChiKey: KBYGVGRFSYWDBH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.17
• 重原子数：
  31.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  78.9
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  在 四(三苯基膦)钯 、 三正丁基氢锡 、 lithium chloride 作用下， 反应 3.0h， 以19%的产率得到ethyl 2,6-bis(trifluoromethyl)-2H-1-benzopyran-3-carboxylate
  参考文献：
  名称：

  The novel benzopyran class of selective cyclooxygenase-2 inhibitors. Part III: The three microdose candidates

  摘要：

  In this manuscript, we report the discovery of the substituted 2-trifluoromethyl-2H-benzopyran-3-carboxylic acids as a novel series of potent and selective cyclooxygenase-2 (COX-2) inhibitors. We provide the structure-activity relationships, optimization of design, testing criteria, and human half-life data. The challenge of a surprisingly long half-life (t(1/2) = 360 h) of the first clinical candidate 1 and human t(1/2) had been difficult to predict based on allometric scaling for this class of highly ppb compounds. We used a microdose strategy which led to the discovery of clinical agents 18c-(S), 29b-(S), and 34b-(S) with human half-life of 57, 13, and 11 h. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.07.059
• 作为产物：
  描述：

  三氟甲磺酸酐 、 在 2,6-二叔丁基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 以66%的产率得到
  参考文献：
  名称：

  The novel benzopyran class of selective cyclooxygenase-2 inhibitors. Part III: The three microdose candidates

  摘要：

  In this manuscript, we report the discovery of the substituted 2-trifluoromethyl-2H-benzopyran-3-carboxylic acids as a novel series of potent and selective cyclooxygenase-2 (COX-2) inhibitors. We provide the structure-activity relationships, optimization of design, testing criteria, and human half-life data. The challenge of a surprisingly long half-life (t(1/2) = 360 h) of the first clinical candidate 1 and human t(1/2) had been difficult to predict based on allometric scaling for this class of highly ppb compounds. We used a microdose strategy which led to the discovery of clinical agents 18c-(S), 29b-(S), and 34b-(S) with human half-life of 57, 13, and 11 h. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.07.059