tert-butyl 4-amino-2-(2,2-dimethylpropyl)-6,6-dimethyl-5,7-dihydro-4H-benzimidazole-1-carboxylate | 1414357-18-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: tert-butyl 4-amino-2-(2,2-dimethylpropyl)-6,6-dimethyl-5,7-dihydro-4H-benzimidazole-1-carboxylate
• CAS: 1414357-18-8
• 化学式: C₁₉H₃₃N₃O₂
• 分子量: 335.49
• InChiKey: YYMKGXKOBZUAHQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  70.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl 4-amino-2-(2,2-dimethylpropyl)-6,6-dimethyl-5,7-dihydro-4H-benzimidazole-1-carboxylate 在 乙醇 作用下， 以 二氯甲烷 为溶剂， 生成 N-[(2S,3R)-4-[[2-(2,2-dimethylpropyl)-6,6-dimethyl-1,4,5,7-tetrahydrobenzimidazol-4-yl]amino]-3-hydroxy-1-phenylbutan-2-yl]acetamide
  参考文献：
  名称：

  Design and synthesis of potent hydroxyethylamine (HEA) BACE-1 inhibitors carrying prime side 4,5,6,7-tetrahydrobenzazole and 4,5,6,7-tetrahydropyridinoazole templates

  摘要：

  A set of low molecular weight compounds containing a hydroxyethylamine (HEA) core structure with different prime side alkyl substituted 4,5,6,7-tetrahydrobenzazoles and one 4,5,6,7-tetrahydropyridinoazole was synthesized. Striking differences were observed on potencies in the BACE-1 enzymatic and cellular assays depending on the nature of the heteroatoms in the bicyclic ring, from the low active compound 4 to inhibitor 6, displaying BACE-1 IC50 values of 44 nM (enzyme assay) and 65 nM (cell-based assay). (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.08.097
• 作为产物：
  描述：

  tert-butyl 4-azido-2-(2,2-dimethylpropyl)-6,6-dimethyl-5,7-dihydro-4H-benzimidazole-1-carboxylate 在 hydrazine hydrate 作用下， 以 乙醇 、 水 为溶剂， 生成 tert-butyl 4-amino-2-(2,2-dimethylpropyl)-6,6-dimethyl-5,7-dihydro-4H-benzimidazole-1-carboxylate
  参考文献：
  名称：

  Design and synthesis of potent hydroxyethylamine (HEA) BACE-1 inhibitors carrying prime side 4,5,6,7-tetrahydrobenzazole and 4,5,6,7-tetrahydropyridinoazole templates

  摘要：

  A set of low molecular weight compounds containing a hydroxyethylamine (HEA) core structure with different prime side alkyl substituted 4,5,6,7-tetrahydrobenzazoles and one 4,5,6,7-tetrahydropyridinoazole was synthesized. Striking differences were observed on potencies in the BACE-1 enzymatic and cellular assays depending on the nature of the heteroatoms in the bicyclic ring, from the low active compound 4 to inhibitor 6, displaying BACE-1 IC50 values of 44 nM (enzyme assay) and 65 nM (cell-based assay). (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.08.097