3-甲基氨基-1,2,3,4-四氢咔唑 | 22350-03-4

• 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: 3-甲基氨基-1,2,3,4-四氢咔唑
• 英文名称: methyl-(1,2,4,9-tetrahydro-1H-carbazol-3-yl)amine
• 英文别名: N-methyl-(2,3,4,9-tetrahydro-1H-carbazol-3-yl)amine；1,2,3,4-Tetrahydro-3-methylaminocarbazol；3-(Methylamino)-1,2,3,4-tetrahydrocarbazol；methyl-(1,2,3,4-tetrahydro-carbazol-3-yl)-amine；3-(methylamino)-1,2,3,4-tetrahydrocarbazole；N-methyl-2,3,4,9-tetrahydro-1H-carbazol-3-amine
• CAS: 22350-03-4
• 化学式: C₁₃H₁₆N₂
• 分子量: 200.283
• InChiKey: GHRYJTRLPDSVOY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  27.8
• 氢给体数：
  2
• 氢受体数：
  1

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  3-甲基氨基-1,2,3,4-四氢咔唑 在 sodium hydride 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 25.0h， 生成 3-{3-[(4-Fluoro-benzenesulfonyl)-methyl-amino]-1,2,3,4-tetrahydro-carbazol-9-yl}-propionic acid ethyl ester
  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：

  1,4-环己二酮单乙二醇缩酮 在 硫酸 作用下， 以 氘代甲醇-d 、 水 为溶剂， 反应 20.0h， 生成 3-甲基氨基-1,2,3,4-四氢咔唑
  参考文献：
  名称：

  N,N-Dimethyl-[9-(arylsulfonyl)-2,3,4,9-tetrahydro-1H-carbazol-3-yl]amines as novel, potent and selective 5-HT6 receptor antagonists

  摘要：

  The design, synthesis and SAR of novel tetrahydrocarbazole derivatives having 5-HT6 receptor antagonist activity is presented. The racemic compound 15e was found to possess desirable pharmacokinetic properties, adequate brain penetration and activity in animal models of cognition. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.06.002

文献信息

• 2,3-oxidosqualene-lanosterol cyclase inhibitors
  申请人：——

  公开号：US20020045777A1

  公开（公告）日：2002-04-18

  The present invention relates to aminocyclohexanol derivatives useful for the treatment and/or prophylaxis of diseases which are associated with 2,3-oxidosqualene-lanosterol cyclase such as hypercholesterolemia, hyperlipemia, arteriosclerosis, vascular diseases, mycoses, gallstones, tumors and/or hyperproliferative disorders, and treatment and/or prophylaxis of impaired glucose tolerance and diabetes.

  本发明涉及氨基环己醇衍生物，用于治疗和/或预防与2,3-氧化甾二烯-鲨烯合酶相关的疾病，如高胆固醇血症、高脂血症、动脉硬化、血管疾病、真菌病、胆结石、肿瘤和/或增生性疾病，以及治疗和/或预防糖耐量受损和糖尿病。
• 3-Hydroxy carbazole derivatives
  申请人：Sterling Drug Inc.

  公开号：US04062864A1

  公开（公告）日：1977-12-13

  3-(Substituted-amino)-1,2,3,4-tetrahydrocarbazoles are prepared by reacting appropriate 4-substituted-aminocyclohexanones with a phenylhydrazine, by reacting a 3-(sulfonyloxy)-1,2,3,4-tetrahydrocarbazole with an appropriate substituted amine, or by reduction of an appropriate 3-(acylamino)-1,2,3,4-tetrahydrocarbazole. The 3-(substituted-amino)-1,2,3,4-tetrahydrocarbazoles of this invention have analgetic and psychotropic activities. Moreover, certain of these compounds also have antihistaminic activity.

  3-(取代氨基)-1,2,3,4-四氢咔唑烯通过将适当的4-取代氨基环己酮与苯基肼反应制备，通过将3-(磺酸酯氧基)-1,2,3,4-四氢咔唑烯与适当的取代胺反应制备，或者通过还原适当的3-(酰胺基)-1,2,3,4-四氢咔唑烯来制备。本发明的3-(取代氨基)-1,2,3,4-四氢咔唑烯具有镇痛和精神活性。此外，其中一些化合物还具有抗组胺活性。
• Substituted cyclohexane derivatives
  申请人：——

  公开号：US20030186984A1

  公开（公告）日：2003-10-02

  The present invention relates to compounds of formula (I) 1 wherein A 1 , A 2 , A 3 , A 4 , A 5 , A 6 , U, V, m, n and o are as defined in the specification, and pharmaceutically acceptable salts thereof. The compounds are useful for the treatment and/or prophylaxis of diseases which are associated with the 2,3-oxidosqualene-lanosterol cyclase biosynthetic pathway such as hypercholesterolemia and hyperlipemia.

  本发明涉及式(I)的化合物，其中A1、A2、A3、A4、A5、A6、U、V、m、n和o如规范中定义的那样，以及其药学上可接受的盐。这些化合物对于治疗和/或预防与2,3-氧化甾二烯-鲨烯合成途径相关的疾病，如高胆固醇血症和高脂血症，是有用的。
• [EN] COMPOSITIONS AND METHODS FOR G-PROTEIN-COUPLED RECEPTOR 44 DETECTION<br/>[FR] COMPOSITIONS ET PROCÉDÉS DE DÉTECTION DU RÉCEPTEUR 44 COUPLÉ À LA PROTÉINE G
  申请人：HOPE CITY

  公开号：WO2022046605A1

  公开（公告）日：2022-03-03

  Disclosed herein, inter alia, are compounds and methods for G-protein- coupled receptor 44 detection.

  本文披露了用于检测G蛋白偶联受体44的化合物和方法，其中包括其他内容。
• 3-Amino-tetrahydrocarbazoles
  申请人：Sterling Drug Inc.

  公开号：US04172834A1

  公开（公告）日：1979-10-30

  3-(Substituted-amino)-1,2,3,4-tetrahydrocarbazoles are prepared by reacting appropriate 4-substituted-aminocyclohexanones with a phenylhydrazine, by reacting a 3-(sulfonyloxy)-1,2,3,4-tetrahydrocarbazole with an appropriate substituted amine, or by reduction of an appropriate 3-(acylamino)-1,2,3,4-tetrahydrocarbazole. The 3-(substituted-amino)-1,2,3,4-tetrahydrocarbazoles of this invention have analgetic and psychotropic activities. Moreover, certain of these compounds also have antihistaminic activity.

  本发明涉及通过将适当的4-取代氨基环己酮与苯肼反应，通过将3-(磺酰氧基)-1,2,3,4-四氢咔唑与适当的取代胺反应，或通过还原适当的3-(酰胺基)-1,2,3,4-四氢咔唑来制备3-(取代氨基)-1,2,3,4-四氢咔唑。本发明的3-(取代氨基)-1,2,3,4-四氢咔唑具有镇痛和精神活性。此外，其中某些化合物还具有抗组胺活性。