methyl 3-(3-bromophenyl)imidazo[1,2-a]pyridine-7-carboxylate | 1595277-90-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: methyl 3-(3-bromophenyl)imidazo[1,2-a]pyridine-7-carboxylate
• 英文别名: methyl 3-(3-bromophenyl)-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine-7-carboxylate
• CAS: 1595277-90-9
• 化学式: C₁₅H₁₅BrN₂O₂
• 分子量: 335.2
• InChiKey: RQYRANCAUGCVTF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.05
• 重原子数：
  20.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  44.12
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  methyl 3-(3-bromophenyl)imidazo[1,2-a]pyridine-7-carboxylate 在 三氟乙酸 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 0.58h， 生成 3-(3-bromophenyl)-5,6-dihydro-2′H,8H-spiro[imidazo[1,2-a]pyridine-7,3′-piperidin]-2′-one
  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
• 作为产物：
  描述：

  3-溴苯乙醇 在 platinum(IV) oxide 、 氢气 、 溴 、 sodium carbonate 、 戴斯-马丁氧化剂 作用下， 以 1,4-二氧六环 、 甲醇 、 乙醚 、 乙醇 、 二氯甲烷 为溶剂， 20.0~120.0 ℃ 、800.01 kPa 条件下， 反应 23.0h， 生成 methyl 3-(3-bromophenyl)imidazo[1,2-a]pyridine-7-carboxylate
  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