methyl 1-isopentyl-5-(3-(tritylamino)propyl)-4,5,6,7-tetrahydro-1H-benzo[d]imidazole-5-carboxylate | 1610943-00-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: methyl 1-isopentyl-5-(3-(tritylamino)propyl)-4,5,6,7-tetrahydro-1H-benzo[d]imidazole-5-carboxylate
• CAS: 1610943-00-4
• 化学式: C₃₆H₄₃N₃O₂
• 分子量: 549.756
• InChiKey: YKFXYOUCEBRABN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.94
• 重原子数：
  41.0
• 可旋转键数：
  12.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  56.15
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  methyl 1-isopentyl-5-(3-(tritylamino)propyl)-4,5,6,7-tetrahydro-1H-benzo[d]imidazole-5-carboxylate 在 盐酸 、 氨 、 三氟乙酸 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 水 、 三乙胺 为溶剂， 反应 3.66h， 生成 (5R)-5-(3-aminopropyl)-1-(3-methylbutyl)-4,5,6,7-tetrahydro-1H-benzimidazole-5-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
• 作为产物：
  描述：

  3-Amino-4-(3-methylbutylamino)benzoic acid 在 palladium on activated charcoal 、 氢气 、 palladium diacetate 、 对甲苯磺酸 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 溶剂黄146 为溶剂， 20.0~155.0 ℃ 、800.01 kPa 条件下， 反应 0.67h， 生成 methyl 1-isopentyl-5-(3-(tritylamino)propyl)-4,5,6,7-tetrahydro-1H-benzo[d]imidazole-5-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