(7R)-7-(2-aminopropyl)-3-(2',4'-dichloro-biphenyl-3-yl)-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine-7-carboxylic acid hydrochloride | 1595278-04-8

• 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: (7R)-7-(2-aminopropyl)-3-(2',4'-dichloro-biphenyl-3-yl)-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine-7-carboxylic acid hydrochloride
• 英文别名: (7R)-7-(3-aminopropyl)-3-[3-(2,4-dichlorophenyl)phenyl]-6,8-dihydro-5H-imidazo[1,2-a]pyridine-7-carboxylic acid;hydrochloride
• CAS: 1595278-04-8
• 化学式: C₂₃H₂₃Cl₂N₃O₂*ClH
• 分子量: 480.821
• InChiKey: IOOZRTSDGXVNMZ-GNAFDRTKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  81.1
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-(3-bromophenyl)-5,6-dihydro-2′H,8H-spiro[imidazo[1,2-a]pyridine-7,3′-piperidin]-2′-one 在 盐酸 、 四(三苯基膦)钯 作用下， 以 甲醇 、 乙二醇二甲醚 、 三乙胺 为溶剂， 反应 22.08h， 生成 (7R)-7-(2-aminopropyl)-3-(2',4'-dichloro-biphenyl-3-yl)-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine-7-carboxylic acid hydrochloride
  参考文献：
  名称：

  Design and synthesis of conformationally restricted inhibitors of active thrombin activatable fibrinolysis inhibitor (TAFIa)

  摘要：

  A series of 4,5,6,7-tetrahydro-1H-benzimidazole-5-carboxylic acid and 5,6,7,8-tetrahydroimidazo [1,2-a] pyridine-7-carboxylic acid derivatives designed as inhibitors of TAFIa has been prepared via a common hydrogenation-alkylation sequence starting from the appropriate benzimidazole and imidazopyridine system. We present a successful design strategy using a conformational restriction approach resulting in potent and selective inhibitors of TAFIa. The X-ray structure of compound 5 in complex with a H333Y/H335Q double mutant TAFI indicate that the conformational restriction is responsible for the observed potency increase. (c) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.02.010

文献信息

• Design and synthesis of conformationally restricted inhibitors of active thrombin activatable fibrinolysis inhibitor (TAFIa)
  作者：Mikael Brink、Anders Dahlén、Thomas Olsson、Magnus Polla、Tor Svensson

  DOI：10.1016/j.bmc.2014.02.010

  日期：2014.4

  A series of 4,5,6,7-tetrahydro-1H-benzimidazole-5-carboxylic acid and 5,6,7,8-tetrahydroimidazo [1,2-a] pyridine-7-carboxylic acid derivatives designed as inhibitors of TAFIa has been prepared via a common hydrogenation-alkylation sequence starting from the appropriate benzimidazole and imidazopyridine system. We present a successful design strategy using a conformational restriction approach resulting in potent and selective inhibitors of TAFIa. The X-ray structure of compound 5 in complex with a H333Y/H335Q double mutant TAFI indicate that the conformational restriction is responsible for the observed potency increase. (c) 2014 Elsevier Ltd. All rights reserved.