ethyl [3-(4-fluorobenzenesulfonylamino)-1,2,3,4-tetrahydrocarbazol-9-yl]acetate | 844639-54-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: ethyl [3-(4-fluorobenzenesulfonylamino)-1,2,3,4-tetrahydrocarbazol-9-yl]acetate
• 英文别名: Ethyl 2-[3-[(4-fluorophenyl)sulfonylamino]-1,2,3,4-tetrahydrocarbazol-9-yl]acetate
• CAS: 844639-54-9
• 化学式: C₂₂H₂₃FN₂O₄S
• 分子量: 430.5
• InChiKey: RTYFXDIDKMTKFL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  85.8
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl [3-(4-fluorobenzenesulfonylamino)-1,2,3,4-tetrahydrocarbazol-9-yl]acetate 在 lithium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以95%的产率得到TM30643
  参考文献：
  名称：

  Minor Structural Modifications Convert the Dual TP/CRTH2 Antagonist Ramatroban into a Highly Selective and Potent CRTH2 Antagonist

  摘要：

  Ramatroban, a thromboxane A(2) receptor (TP) antagonist with clinical efficacy in asthma and allergic rhinitis, was recently shown to also antagonize the prostaglandin D-2 receptor CRTH2. Here we report that minor structural changes to ramatroban result in a compound (13) with complete lack of activity on TP but sub-nanomolar potency toward CRTH2. This is the first selective CRTH2 antagonist described to date, and should prove highly valuable in further elucidating the biological significance of CRTH2.

  DOI：

  10.1021/jm049036i
• 作为产物：
  描述：

  ethyl (3-oxo-1,2,3,4-tetrahydrocarbazol-9-yl)acetate glycol ketal 在 盐酸 、 ammonium formate 、 sodium cyanoborohydride 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 反应 56.0h， 生成 ethyl [3-(4-fluorobenzenesulfonylamino)-1,2,3,4-tetrahydrocarbazol-9-yl]acetate
  参考文献：
  名称：

  Minor Structural Modifications Convert the Dual TP/CRTH2 Antagonist Ramatroban into a Highly Selective and Potent CRTH2 Antagonist

  摘要：

  Ramatroban, a thromboxane A(2) receptor (TP) antagonist with clinical efficacy in asthma and allergic rhinitis, was recently shown to also antagonize the prostaglandin D-2 receptor CRTH2. Here we report that minor structural changes to ramatroban result in a compound (13) with complete lack of activity on TP but sub-nanomolar potency toward CRTH2. This is the first selective CRTH2 antagonist described to date, and should prove highly valuable in further elucidating the biological significance of CRTH2.

  DOI：

  10.1021/jm049036i