N-(2-Bromoethyl)-4,4-dimethyl-6-benzoyl-1,2,3,4-tetrahydroquinoline | 900865-02-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(2-Bromoethyl)-4,4-dimethyl-6-benzoyl-1,2,3,4-tetrahydroquinoline
• 英文别名: [1-(2-bromoethyl)-4,4-dimethyl-2,3-dihydroquinolin-6-yl]-phenylmethanone
• CAS: 900865-02-3
• 化学式: C₂₀H₂₂BrNO
• 分子量: 372.305
• InChiKey: VTEQDHQJIZPDOL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(2-Bromoethyl)-4,4-dimethyl-6-benzoyl-1,2,3,4-tetrahydroquinoline 、 对羟基苯甲醛 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以65%的产率得到
  参考文献：
  名称：

  4,4-Dimethyl-1,2,3,4-tetrahydroquinoline-based PPARα/γ agonists. Part I: Synthesis and pharmacological evaluation

  摘要：

  Type-2 diabetes (T2D) is a complex metabolic disease characterized by insulin resistance in the liver and peripheral tissues accompanied by a defect in pancreatic beta-cell. Since their discovery three subtypes of Peroxisomes Proliferators Activated Receptors were identified namely PPAR alpha, PPAR gamma and PPAR beta/(delta). We were interested in designing novel PPAR gamma selective agonists and/or dual PPAR alpha/gamma agonists. Based on the typical topology of synthetic PPAR agonists, we focused our design approach on 4,4-dimethyl-1,2,3,4-tetrahydroquinoline as novel cyclic tail. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.01.067
• 作为产物：
  描述：

  N-(2-Bromoethyl)-4,4-dimethyl-1,2,3,4-tetrahydroquinoline 、 苯甲酰氯 在 四氯化钛 作用下， 以 1,2-二氯乙烷 为溶剂， 以71%的产率得到N-(2-Bromoethyl)-4,4-dimethyl-6-benzoyl-1,2,3,4-tetrahydroquinoline
  参考文献：
  名称：

  4,4-Dimethyl-1,2,3,4-tetrahydroquinoline-based PPARα/γ agonists. Part I: Synthesis and pharmacological evaluation

  摘要：

  Type-2 diabetes (T2D) is a complex metabolic disease characterized by insulin resistance in the liver and peripheral tissues accompanied by a defect in pancreatic beta-cell. Since their discovery three subtypes of Peroxisomes Proliferators Activated Receptors were identified namely PPAR alpha, PPAR gamma and PPAR beta/(delta). We were interested in designing novel PPAR gamma selective agonists and/or dual PPAR alpha/gamma agonists. Based on the typical topology of synthetic PPAR agonists, we focused our design approach on 4,4-dimethyl-1,2,3,4-tetrahydroquinoline as novel cyclic tail. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.01.067

文献信息

• 4,4-Dimethyl-1,2,3,4-tetrahydroquinoline-based PPARα/γ agonists. Part. II: Synthesis and pharmacological evaluation of oxime and acidic head group structural variations
  作者：Cécile Parmenon、Jérôme Guillard、Daniel-Henri Caignard、Nathalie Hennuyer、Bart Staels、Valérie Audinot-Bouchez、Jean-Albert Boutin、Catherine Dacquet、Alain Ktorza、Marie-Claude Viaud-Massuard

  DOI：10.1016/j.bmcl.2009.03.143

  日期：2009.5

  Based on the typical topology of synthetic PPAR agonists, we focused our design approach on using 4,4-dimethyl-1,2,3,4-tetrahydroquinoline as a novel cyclic scaffold with oxime and acidic head group structural variations.

  2型糖尿病（T2D）是一种复杂的代谢性疾病，其特征是肝脏和周围组织的胰岛素抵抗伴随着胰腺β细胞的缺乏。自发现以来，已鉴定出过氧化物酶体增殖物激活的受体的三种亚型，即PPARα，PPARγ和PPARβ/（δ）。在这项研究中，我们对设计新型PPARγ选择性激动剂和/或双重PPARα/γ激动剂感兴趣。基于合成的PPAR激动剂的典型拓扑结构，我们将设计方法集中于使用4,4-二甲基-1,2,3,4-四氢喹啉作为具有肟和酸性头基结构变化的新型环状支架。
• Heterocyclic Oxime Compounds a Process for Their Preparation and Pharmaceutical Compositions Containing Them
  申请人：Parmenon Cicile

  公开号：US20090124656A1

  公开（公告）日：2009-05-14

  Compounds of formula (I): wherein: R 1 , R 2 , R 3 , R 4 and X are as defined in the description, A represents an alkylene chain as defined in the description, B represents an alkyl or alkenyl group substituted by a group or R 7 , or B represents a group or R 7 . Medicinal products containing the same which are useful as hypoglycaemic and hypolipaemic agents.

  式(I)的化合物：其中：R1、R2、R3、R4和X如描述中所定义，A表示如描述中所定义的烷基链，B表示被基团或R7取代的烷基或烯基，或者B表示基团或R7。含有上述化合物的药物，可用作降血糖和降脂药物。