ethyl {3-[(4-fluorobenzenesulfonyl)methylamino]-1,2,3,4-tetrahydrocarbazol-9-yl}acetate | 844639-55-0

• 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-fluorobenzenesulfonyl)methylamino]-1,2,3,4-tetrahydrocarbazol-9-yl}acetate
• 英文别名: Ethyl 2-[3-[(4-fluorophenyl)sulfonyl-methylamino]-1,2,3,4-tetrahydrocarbazol-9-yl]acetate
• CAS: 844639-55-0
• 化学式: C₂₃H₂₅FN₂O₄S
• 分子量: 444.527
• InChiKey: LQIYAPITGJFGEX-UHFFFAOYSA-N

物化性质

• 沸点：
  604.7±65.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  31
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  77
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl {3-[(4-fluorobenzenesulfonyl)methylamino]-1,2,3,4-tetrahydrocarbazol-9-yl}acetate 在 lithium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以34%的产率得到2-[3-[（4-氟苯基）磺酰基-甲基氨基]-1,2,3,4-四氢咔唑-9-基]乙酸
  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 、 溶剂黄146 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 反应 28.25h， 生成 ethyl {3-[(4-fluorobenzenesulfonyl)methylamino]-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

文献信息

• Minor Structural Modifications Convert the Dual TP/CRTH2 Antagonist Ramatroban into a Highly Selective and Potent CRTH2 Antagonist
  作者：Trond Ulven、Evi Kostenis

  DOI：10.1021/jm049036i

  日期：2005.2.1

  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.