1-(6-amino-3,4-dihydroquinolin-1(2H)-yl)ethanone | 27392-71-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 1-(6-amino-3,4-dihydroquinolin-1(2H)-yl)ethanone
• 英文别名: 1-(6-amino-1,2,3,4-tetrahydroquinolin)ethanone；1-acetyl-6-amino-1,2,3,4-tetrahydroquinoline；6-Amino-1-acetyl-1,2,3,4-tetrahydrochinolin；1-(6-amino-3,4-dihydro-2H-quinolin-1-yl)ethanone
• CAS: 27392-71-8
• 化学式: C₁₁H₁₄N₂O
• mdl: MFCD10016626
• 分子量: 190.245
• InChiKey: VORCSTVWTCFCFA-UHFFFAOYSA-N

物化性质

• 沸点：
  477.5±45.0 °C(Predicted)
• 密度：
  1.182±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.363
• 拓扑面积：
  46.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(6-amino-3,4-dihydroquinolin-1(2H)-yl)ethanone 在 sodium hydroxide 、 sodium hydride 、 potassium carbonate 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 甲醇 、 乙醇 、 1,2-二氯乙烷 为溶剂， 反应 115.83h， 生成 1-methyl-5,6,7,8-tetrahydro-1H-pyrrolo<2,3-g>quinoline
  参考文献：
  名称：

  5-Methyl-1-(3-pyridylcarbamoyl)-1,2,3,5-tetrahydropyrrolo[2,3-f]indole: A Novel 5-HT2C/5-HT2B Receptor Antagonist with Improved Affinity, Selectivity, and Oral Activity

  摘要：

  The preparation of a series of conformationally restricted analogues of indolylurea 1, namely tetrahydropyrroloindoles and tetrahydropyrroloquinolines, is described. The binding affinities of these compounds at 5-HT2A, 5-HT2B, and 5-HT2C receptors were determined. Of these compounds, the 1,2,3,5-tetrahydropyrrolo[2,3-f]indole derivative, compound 11, was found to have high affinity for the 5-HT2C (pK(I) 8.0) and 5-HT2B receptors (pA(2) 8.5), with excellent selectivity over the 5-HT2A and various other receptors (pK(I) <6). 11 is also considerably more active than 1 in both an in vitro functional model, 5-HT-stimulated phosphoinositol hydrolysis (pK(B) 8.8), and an in vivo functional model, mCPP-induced hypolocomotion (ID50 5.5 mg/kg po). 11 should therefore be of significant utility as a pharmacological tool to delineate the functional significance of blockade of 5-HT2B and 5-HT2C receptors.

  DOI：

  10.1021/jm00014a004
• 作为产物：
  描述：

  6-氨基喹啉 在 吡啶 、 sodium hydroxide 、 sodium tetrahydroborate 、 三乙胺 、 nickel dichloride 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 氯仿 为溶剂， 反应 9.5h， 生成 1-(6-amino-3,4-dihydroquinolin-1(2H)-yl)ethanone
  参考文献：
  名称：

  5-Methyl-1-(3-pyridylcarbamoyl)-1,2,3,5-tetrahydropyrrolo[2,3-f]indole: A Novel 5-HT2C/5-HT2B Receptor Antagonist with Improved Affinity, Selectivity, and Oral Activity

  摘要：

  The preparation of a series of conformationally restricted analogues of indolylurea 1, namely tetrahydropyrroloindoles and tetrahydropyrroloquinolines, is described. The binding affinities of these compounds at 5-HT2A, 5-HT2B, and 5-HT2C receptors were determined. Of these compounds, the 1,2,3,5-tetrahydropyrrolo[2,3-f]indole derivative, compound 11, was found to have high affinity for the 5-HT2C (pK(I) 8.0) and 5-HT2B receptors (pA(2) 8.5), with excellent selectivity over the 5-HT2A and various other receptors (pK(I) <6). 11 is also considerably more active than 1 in both an in vitro functional model, 5-HT-stimulated phosphoinositol hydrolysis (pK(B) 8.8), and an in vivo functional model, mCPP-induced hypolocomotion (ID50 5.5 mg/kg po). 11 should therefore be of significant utility as a pharmacological tool to delineate the functional significance of blockade of 5-HT2B and 5-HT2C receptors.

  DOI：

  10.1021/jm00014a004

文献信息

• [EN] CARBOXAMIDES AS UBIQUITIN-SPECIFIC PROTEASE INHIBITORS<br/>[FR] CARBOXAMIDES UTILISÉES EN TANT QU'INHIBITEURS DE PROTÉASE SPÉCIFIQUE DE L'UBIQUITINE
  申请人：FORMA THERAPEUTICS INC

  公开号：WO2019032863A1

  公开（公告）日：2019-02-14

  The present disclosure relates to modulators, such as inhibitors, of at least one pathway chosen from USP28 and USP25, pharmaceutical compositions comprising the inhibitors, and methods of using the inhibitors. The modulators, such as inhibitors, of at least one pathway chosen from USP28 and USP25 can be useful in the treatment of cancers, among other ailments.

  本公开涉及调节剂，如抑制剂，至少选择自USP28和USP25中的一条途径的药物组合物包括这些抑制剂，以及使用这些抑制剂的方法。这些调节剂，如抑制剂，至少选择自USP28和USP25中的一条途径，可用于治疗癌症等疾病。
• [EN] HEAT SHOCK PROTEIN 90 INHIBITORS<br/>[FR] INHIBITEURS DE LA PROTÉINE DE CHOC THERMIQUE 90
  申请人：UNIV TAIPEI MEDICAL

  公开号：WO2018171575A1

  公开（公告）日：2018-09-27

  Substituted aromatic compounds of formula (I) shown below: (formula I) The definition of each variable in formula (I) appears in the Specification. Also disclosed is a pharmaceutical composition containing one of the substituted aromatic compounds. Further disclosed is a method of using one of these compounds for treating a medical condition associated with HSP90.

  以下是公式（I）中所示的取代芳香化合物：（公式I）。公式（I）中每个变量的定义出现在规范中。还披露了含有其中一种取代芳香化合物的药物组合物。进一步披露了使用这些化合物中的一种来治疗与HSP90相关的医疗状况的方法。
• Discovery and Optimization of <i>N</i>-Acyl-6-sulfonamide-tetrahydroquinoline Derivatives as Novel Non-Steroidal Selective Glucocorticoid Receptor Modulators
  作者：Dan Li、Xiaodong Bao、Jinping Pang、Xueping Hu、Longling Wang、Jiajia Wang、Zhaoxu Yang、Lei Xu、Siyu Wang、Qinjie Weng、Sunliang Cui、Tingjun Hou

  DOI：10.1021/acs.jmedchem.2c01082

  日期：2022.12.8

  Selective glucocorticoid receptor modulators (SGRMs), which can dissociate the transactivation from the transrepression of the glucocorticoid receptor (GR), are regarded as very promising therapeutics for inflammatory and autoimmune diseases. We previously discovered a SGRM HP-19 based on the passive antagonistic conformation of GR and bioassays. In this study, we further analyzed the dynamic changes

  选择性糖皮质激素受体调节剂 (SGRM) 可以将反式激活与糖皮质激素受体 (GR) 的反式抑制分离，被认为是非常有前途的炎症和自身免疫性疾病治疗药物。我们之前发现了基于 GR 和生物测定的被动拮抗构象的SGRM HP-19 。本研究进一步分析了HP-19结合后被动拮抗状态的动态变化，通过HP-19的结构优化设计合成了62N- acyl -6-sulfonamide-tetrahydroquinoline衍生物。其中，化合物B53表现出最好的反式抑制活性 (IC 50 NF-κB= 0.009 ± 0.001 μM）与地塞米松（IC 50 NF-κB = 0.005 ± 0.001 μM）相当，并且没有反式激活活性。B53能有效降低炎症因子IL-6、IL-1β、TNF-α等的表达，不良反应较轻，对GR具有高度特异性。此外，B53能够通过口服药物干预显着缓解小鼠模型的皮炎。
• Selective Anti-Markovnikov Cyclization and Hydrofluorination Reaction in Superacid HF/SbF₅: A Tool in the Design of Nitrogen-Containing (Fluorinated) Polycyclic Systems
  作者：Guillaume Compain、Céline Bonneau、Agnès Martin-Mingot、Sébastien Thibaudeau

  DOI：10.1021/jo400398y

  日期：2013.5.3

  The selective synthesis of tetrahydroquinolines and fluorinated arylamines was performed in superacid HF/SbF5 through a superelectrophilic ammonium-carbenium activation process. This anti-Markovnikov oriented reaction was applied to the straightforward synthesis of highly valued (fluorinated) nitrogen-containing heterocyclic compounds.
• CONDENSED INDOLE DERIVATIVES AS 5HT 2C? AND 5HT 2B? ANTAGONISTS
  申请人：SMITHKLINE BEECHAM PLC

  公开号：EP0656003A1

  公开（公告）日：1995-06-07