Ethyl 2-(3-amino-1,2,3,4-tetrahydrocarbazol-9-yl)acetate | 844639-52-7

• 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 2-(3-amino-1,2,3,4-tetrahydrocarbazol-9-yl)acetate
• CAS: 844639-52-7
• 化学式: C₁₆H₂₀N₂O₂
• 分子量: 272.347
• InChiKey: VDEXFEFTDOXAEW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Ethyl 2-(3-amino-1,2,3,4-tetrahydrocarbazol-9-yl)acetate 在 lithium hydroxide 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 17.0h， 生成 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 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 40.0h， 生成 Ethyl 2-(3-amino-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