6-氟-2,3,4,9-四氢-1H-咔唑-3-甲酸 | 907211-31-8

• 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
• 中文名称: 6-氟-2,3,4,9-四氢-1H-咔唑-3-甲酸
• 英文名称: 6-fluoro-2,3,4,9-tetrahydro-1H-carbazole-3-carboxylic acid
• CAS: 907211-31-8
• 化学式: C₁₃H₁₂FNO₂
• 分子量: 233.242
• InChiKey: FAWQZNACUZJAJY-UHFFFAOYSA-N

物化性质

• 熔点：
  183-185 °C
• 沸点：
  456.9±45.0 °C(Predicted)
• 密度：
  1.412±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  53.1
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-氟-2,3,4,9-四氢-1H-咔唑-3-甲酸 在 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 草酰氯 、 (-)-cinchonidine 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 二甲基亚砜 、 乙腈 为溶剂， 反应 6.5h， 生成 (S,S)-(6-fluoro-2,3,4,9-tetrahydro-1H-carbazol-3-ylmethyl)-(8-methyl-2,3-dihydro-[1,4]dioxino[2,3-f]quinolin-2-ylmethyl)amine
  参考文献：
  名称：

  First Scale-Up: Problems and Resolutions on the Synthesis of WAY-253752, a Novel, Dual-Acting SSRI/5HT_1A Antagonist

  摘要：

  An alternative synthesis of WAY-253752, 1, a novel, dual-acting SSRI/5HT(1A) antagonist, was developed and used for the first scale-up. Initially, the target compound was synthesized as part of a diasteromeric mixture separated by chiral preparative HPLC. The new route was designed around intermediates suitable for chiral resolution, and its conditions were successfully determined.

  DOI：

  10.1021/op700181n
• 作为产物：
  描述：

  对环己酮甲酸乙酯 在 potassium hydroxide 作用下， 以 乙醇 为溶剂， 反应 19.0h， 生成 6-氟-2,3,4,9-四氢-1H-咔唑-3-甲酸
  参考文献：
  名称：

  First Scale-Up: Problems and Resolutions on the Synthesis of WAY-253752, a Novel, Dual-Acting SSRI/5HT_1A Antagonist

  摘要：

  An alternative synthesis of WAY-253752, 1, a novel, dual-acting SSRI/5HT(1A) antagonist, was developed and used for the first scale-up. Initially, the target compound was synthesized as part of a diasteromeric mixture separated by chiral preparative HPLC. The new route was designed around intermediates suitable for chiral resolution, and its conditions were successfully determined.

  DOI：

  10.1021/op700181n

文献信息

• Novel tetrahydrocarbazole derivatives having improved biological action and improved solubility as ligands of G-protein coupled receptors (GPCRs)
  申请人：Paulini Klaus

  公开号：US20060014818A1

  公开（公告）日：2006-01-19

  The present invention provides novel tetrahydrocarbazole derivatives which have improved properties and which can be employed as inhibitors of GPCRs. This results in the possibility of using the novel compounds to treat pathological conditions whose severity depends on the pathobiochemical effect of GPCRs. The compounds of the invention act in particular via an antagonistic inhibition of the LHRH receptor. The invention further provides medicaments which comprise one or more of the novel compounds as active ingredient. The medicaments are suitable in particular to be employed in an oral dosage form for a mammal, in particular a human.

  本发明提供了新颖的四氢咔唑衍生物，具有改进的性能，并可用作GPCR的抑制剂。这导致可以利用这些新型化合物来治疗病理条件，其严重程度取决于GPCR的病理生物化学效应。本发明的化合物特别通过对LHRH受体的拮抗性抑制发挥作用。本发明还提供了包含一种或多种新型化合物作为活性成分的药物。这些药物特别适合用于口服剂型，用于哺乳动物，特别是人类。
• [EN] 3-AMINO CHOMAN AND 2-AMINO TETRALIN DERIVATIVES<br/>[FR] DERIVES 3-AMINO CHOMANE ET 2-AMINO TETRALINE
  申请人：WYETH CORP

  公开号：WO2005012291A1

  公开（公告）日：2005-02-10

  3-Amino chroman and 2-amino tetralin derivatives and compositions containing such compounds are disclosed. Methods of using the 3-amino chroman and 2-amino tetralin compounds and compositions containing such compounds in the treatment of serotonin disorders, such as depression and anxiety, are also disclosed.

  揭示了3-氨基色苷和2-氨基四氢萘衍生物以及含有这些化合物的组合物。还揭示了在治疗血清素失调症，如抑郁症和焦虑症中使用3-氨基色苷和2-氨基四氢萘化合物以及含有这些化合物的组合物的方法。
• 3-Amino chroman and 2-amino tetralin derivatives
  申请人：Hatzenbuhler Theriault Nicole

  公开号：US20050032873A1

  公开（公告）日：2005-02-10

  3-Amino chroman and 2-amino tetralin derivatives and compositions containing such compounds are disclosed. Methods of using the 3-amino chroman and 2-amino tetralin compounds and compositions containing such compounds in the treatment of serotonin disorders, such as depression and anxiety, are also disclosed.

  本文披露了3-氨基色满和2-氨基四氢萘衍生物及含有这些化合物的组合物。还披露了使用3-氨基色满和2-氨基四氢萘化合物及含有这些化合物的组合物治疗血清素失调症，如抑郁和焦虑的方法。
• Cycloalkylfused indole, benzothiophene, benzofuran and indene derivatives
  申请人：Sabb Louise Annmarie

  公开号：US20060205759A1

  公开（公告）日：2006-09-14

  The present invention provides cycloalkylfused indole, benzothiophene, benzofuran, and indene derivatives, and methods for using them to, for example, treat, prevent and/or ameliorate central nervous system diseases by antagonizing 5-HT 1A receptors and modulating serotonin levels.

  本发明提供环烷基融合吲哚、苯并噻吩、苯并呋喃和茚烯衍生物，以及使用它们的方法，例如通过拮抗5-HT1A受体和调节血清素水平来治疗、预防和/或改善中枢神经系统疾病。
• CYCLOALKYLFUSED INDOLE, BENZOTHIOPHENE, BENZOFURAN AND INDENE DERIVATIVES
  申请人：Sabb Louise Annmarie

  公开号：US20080081910A1

  公开（公告）日：2008-04-03

  The present invention provides cycloalkylfused indole, benzothiophene, benzofuran, and indene derivatives, and methods for using them to, for example, treat, prevent and/or ameliorate central nervous system diseases by antagonizing 5-HT 1A receptors and modulating serotonin levels.

  本发明提供了环烷基融合吲哚、苯并噻吩、苯并呋喃和茚烯衍生物，以及使用它们的方法，例如通过拮抗5-HT1A受体和调节血清素水平来治疗、预防和/或改善中枢神经系统疾病。