1-methyl-2,3-dihydro-1H-pyrrolo[2,3-b]quinolin-4-ylamine

• 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-methyl-2,3-dihydro-1H-pyrrolo[2,3-b]quinolin-4-ylamine
• 英文别名: 4-amino-1-methyl-2,3-dihydro-1H-pyrrolo[2,3-b] quinoline；1-Methyl-2,3-dihydropyrrolo[2,3-b]quinolin-4-amine
• 化学式: C₁₂H₁₃N₃
• 分子量: 199.255
• InChiKey: HQMPUWYVYYFFSK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  42.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  邻氨基三氟甲苯 在 sodium hexamethyldisilazane 、 三氯氧磷 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 反应 8.0h， 生成 1-methyl-2,3-dihydro-1H-pyrrolo[2,3-b]quinolin-4-ylamine
  参考文献：
  名称：

  A novel and highly efficient synthesis of the aza analogs of tacrine

  摘要：

  We describe a new and efficient synthesis of the aza analogs of tacrine based upon the chemistry of the anionically activated trifluoromethyl group. We identify four sites (A-D) which can be successfully altered to afford the desired fused tricyclic heterocycles in high yield (63-82%). The reaction is believed to proceed through the formation of a quinone methide intermediate. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)01122-3

文献信息

• Quinoline compound
  申请人：UBE INDUSTRIES, LTD.

  公开号：EP0430485A3

  公开（公告）日：1992-01-22

  There is disclosed a quinoline compound represented by the following formula (I): wherein R¹ and R² each represent a hydrogen atom, a halogen atom, a lower alkyl group, a trifluoromethyl group, a hydroxyl group, a lower alkoxy group, a lower alkanoyloxy group, a nitro group, an amino group or a lower alkanoylamino group; R³ represents a hydrogen atom, an alkyl group having 1 to 15 carbon atoms, a cycloalkyl group, an aralkyl group having 7 to 15 carbon atoms which may be substituted by a halogen atom, a lower alkyl group or a lower alkoxy group, an alkanoyl group having 2 to 15 carbon atoms, or a benzoyl group which may be substituted by a halogen atom, a lower alkyl group, a lower alkoxy group, a nitro group, a hydroxy group or an amino group; and n represents an integer of 2 to 5, and an acid addition salt thereof.

  公开了以下式(I)所表示的喹啉化合物： 其中R¹和R²分别表示氢原子、卤素原子、较低的烷基基团、三氟甲基基团、羟基、较低的烷氧基、较低的烷酰氧基、硝基、氨基或较低的烷酰氨基；R³表示氢原子、具有1至15个碳原子的烷基基团、环烷基基团、具有7至15个碳原子的芳基烷基基团，该基团可以被卤素原子、较低的烷基基团或较低的烷氧基取代，具有2至15个碳原子的烷酰基团，或者可以被卤素原子、较低的烷基基团、较低的烷氧基、硝基、羟基或氨基取代的苯甲酰基团；n表示2至5的整数，以及其酸加盐。
• Small molecule toll-like receptor (TLR) antagonists
  申请人：Lipford B. Grayson

  公开号：US20050119273A1

  公开（公告）日：2005-06-02

  The invention provides methods and compositions useful for modulating signaling through Toll-like receptors. The methods involve contacting a TLR-expressing cell with a small molecule having a core structure including at least two rings. Certain of the compounds are 4-primary amino quinolines. Many of the compounds and methods are useful specifically for inhibiting immune stimulation involving at least one of TLR9, TLR8, TLR7, and TLR3. The methods may have use in the treatment of autoimmunity, inflammation, allergy, asthma, graft rejection, graft versus host disease, infection, sepsis, cancer, and immunodeficiency.

  本发明提供了用于调节通过Toll样受体信号传导的方法和组合物。该方法涉及使用含有至少两个环的核心结构的小分子与表达TLR的细胞接触。其中某些化合物是4-主氨基喹啉。许多化合物和方法特别适用于抑制涉及至少一个TLR9、TLR8、TLR7和TLR3的免疫刺激。该方法可用于治疗自身免疫、炎症、过敏、哮喘、移植排斥、移植物抗宿主病、感染、败血症、癌症和免疫缺陷。
• TLR INHIBITOR AND BRUTON'S TYROSINE KINASE INHIBITOR COMBINATIONS
  申请人：Pharmacyclics LLC

  公开号：EP3220912A1

  公开（公告）日：2017-09-27
• JPH03220189A
  申请人：——

  公开号：JPH03220189A

  公开（公告）日：1991-09-27
• US7410975B2
  申请人：——

  公开号：US7410975B2

  公开（公告）日：2008-08-12