3-(3-bromophenyl)-5,6-dihydro-2′H,8H-spiro[imidazo[1,2-a]pyridine-7,3′-piperidin]-2′-one | 1595277-98-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-(3-bromophenyl)-5,6-dihydro-2′H,8H-spiro[imidazo[1,2-a]pyridine-7,3′-piperidin]-2′-one
• CAS: 1595277-98-7
• 化学式: C₁₇H₁₈BrN₃O
• 分子量: 360.253
• InChiKey: JSMCQSNQCNNCRY-UHFFFAOYSA-N

物化性质

• 沸点：
  637.1±50.0 °C(predicted)
• 密度：
  1.58±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.16
• 重原子数：
  22.0
• 可旋转键数：
  1.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  46.92
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  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 7-(3-aminopropyl)-3-phenyl-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