ethyl (3-oxo-1,2,3,4-tetrahydrocarbazol-9-yl)acetate glycol ketal | 844639-50-5

• 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-oxo-1,2,3,4-tetrahydrocarbazol-9-yl)acetate glycol ketal
• 英文别名: Ethyl 2-(1,2,3,4-tetrahydrospiro[carbazole-3,2'-[1,3]dioxolan]-9-yl)acetate；ethyl 2-spiro[1,3-dioxolane-2,3'-2,4-dihydro-1H-carbazole]-9'-ylacetate
• CAS: 844639-50-5
• 化学式: C₁₈H₂₁NO₄
• 分子量: 315.369
• InChiKey: RXUIJPYBRBLVND-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  49.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl (3-oxo-1,2,3,4-tetrahydrocarbazol-9-yl)acetate glycol ketal 在 盐酸 、 lithium hydroxide 、 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 40.25h， 生成 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：

  溴乙酸乙酯 、 1,2,4,9-tetrahydrospiro[carbazole-3,2'-[1,3]dioxolane] 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 13.0h， 以88%的产率得到ethyl (3-oxo-1,2,3,4-tetrahydrocarbazol-9-yl)acetate glycol ketal
  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

• 3-(HETEROARYL-AMINO)-1,2,3,4-TETRAHYDRO-9H-CARBAZOLE DERIVATIVES AND THEIR USE AS PROSTAGLANDIN D2 RECEPTOR MODULATORS
  申请人：Aissaoui Hamed

  公开号：US20130065902A1

  公开（公告）日：2013-03-14

  The present invention relates to 3-(heteroaryl-amino)-1,2,3,4-tetrahydro-9H-carbazole derivatives of the formula (I), wherein R 1 , R 2 and R 3 are as described in the description and their use as prostaglandin receptor modulators, most particularly as prostaglandin D 2 receptor modulators, in the treatment of various prostaglandin-mediated diseases and disorders, to pharmaceutical compositions containing these compounds and to processes for their preparation.

  本发明涉及式(I)的3-(杂环芳基氨基)-1,2,3,4-四氢-9H-咔唑衍生物，其中R1、R2和R3如描述中所述，并且它们作为前列腺素受体调节剂的用途，尤其是作为前列腺素D2受体调节剂，在治疗各种前列腺素介导的疾病和紊乱中的应用，以及含有这些化合物的药物组合物和其制备方法。
• [EN] 3-(HETEROARYL-AMINO)-1,2,3,4-TETRAHYDRO-9H-CARBAZOLE DERIVATIVES AND THEIR USE AS PROSTAGLANDIN D2 RECEPTOR MODULATORS<br/>[FR] DÉRIVÉS DE 3-(HÉTÉROARYLAMINO)-1,2,3,4-TÉTRAHYDRO-9H-CARBAZOLE ET LEUR UTILISATION COMME MODULATEURS DU RÉCEPTEUR DE LA PROSTAGLANDINE D2
  申请人：ACTELION PHARMACEUTICALS LTD

  公开号：WO2011117798A1

  公开（公告）日：2011-09-29

  The present invention relates to 3-(heteroaryl-amino)-1,2,3,4-tetrahydro-9H-carbazole derivatives of the formula (I), wherein R1, R2 and R3 are as described in the description and their use as prostaglandin receptor modulators, most particularly as prostaglandin D2 receptor modulators, in the treatment of various prostaglandin-mediated diseases and disorders, to pharmaceutical compositions containing these compounds and to processes for their preparation.

  本发明涉及公式(I)所示的3-(杂环芳基氨基)-1,2,3,4-四氢-9H-咔唑衍生物，其中R1、R2和R3如描述中所述，并且它们作为前列腺素受体调节剂的用途，特别是作为前列腺素D2受体调节剂，在治疗各种前列腺素介导的疾病和紊乱中的应用，以及包含这些化合物的药物组合物和它们的制备方法。
• US8697869B2
  申请人：——

  公开号：US8697869B2

  公开（公告）日：2014-04-15
• 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.