tert-butyl 4-(((1-isopropyl-4-nitro-1H-benzo[d]imidazol-6-yl)oxy)methyl)piperidine-1-carboxylate | 1262957-48-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: tert-butyl 4-(((1-isopropyl-4-nitro-1H-benzo[d]imidazol-6-yl)oxy)methyl)piperidine-1-carboxylate
• CAS: 1262957-48-1
• 化学式: C₂₁H₃₀N₄O₅
• 分子量: 418.493
• InChiKey: RZKJJVHWXKIMFM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.55
• 重原子数：
  30.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  99.73
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  tert-butyl 4-(((1-isopropyl-4-nitro-1H-benzo[d]imidazol-6-yl)oxy)methyl)piperidine-1-carboxylate 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙醇 为溶剂， 23.0 ℃ 、344.75 kPa 条件下， 反应 5.0h， 生成 tert-butyl 4-(((4-amino-1-isopropyl-1H-benzo[d]imidazol-6-yl)oxy)methyl)piperidine-1-carboxylate
  参考文献：
  名称：

  Design, synthesis, and testing of an 6-O-linked series of benzimidazole based inhibitors of CDK5/p25

  摘要：

  Alzheimer's disease (AD) is a progressive neurodegenerative disease resulting in cognitive and behavioral impairment. The two classic pathological hallmarks of AD include extraneuronal deposition of amyloid beta (A beta) and intraneuronal formation of neurofibrillary tangles (NFTs). NFTs contain hyperphosphorylated tau. Tau is the major microtubule-associated protein in neurons and stabilizes microtubules (MTs). Cyclin dependent kinase 5 (CDK5), when activated by the regulatory binding protein p25, phosphorylates tau at a number of proline-directed serine/threonine residues, resulting in formation of phosphorylated tau as paired helical filaments (PHFs) then in subsequent deposition of PHFs as NFTs. Beginning with the structure of Roscovitine, a moderately selective CDK5 inhibitor, we sought to conduct structural modifications to increase inhibitory potency of CDK5 and increase selectivity over a similar enzyme, cyclin dependent kinase 2 (CDK2). The design, synthesis, and testing of a series of 1-isopropyl-4-aminobenzyl-6-ether-linked benzimidazoles is presented. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.11.022
• 作为产物：
  描述：

  1-isopropyl-4-nitro-1H-benzo[d]imidazol-6-ol 、 N-Boc-4-哌啶甲醇 在 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 tert-butyl 4-(((1-isopropyl-4-nitro-1H-benzo[d]imidazol-6-yl)oxy)methyl)piperidine-1-carboxylate
  参考文献：
  名称：

  Design, synthesis, and testing of an 6-O-linked series of benzimidazole based inhibitors of CDK5/p25

  摘要：

  Alzheimer's disease (AD) is a progressive neurodegenerative disease resulting in cognitive and behavioral impairment. The two classic pathological hallmarks of AD include extraneuronal deposition of amyloid beta (A beta) and intraneuronal formation of neurofibrillary tangles (NFTs). NFTs contain hyperphosphorylated tau. Tau is the major microtubule-associated protein in neurons and stabilizes microtubules (MTs). Cyclin dependent kinase 5 (CDK5), when activated by the regulatory binding protein p25, phosphorylates tau at a number of proline-directed serine/threonine residues, resulting in formation of phosphorylated tau as paired helical filaments (PHFs) then in subsequent deposition of PHFs as NFTs. Beginning with the structure of Roscovitine, a moderately selective CDK5 inhibitor, we sought to conduct structural modifications to increase inhibitory potency of CDK5 and increase selectivity over a similar enzyme, cyclin dependent kinase 2 (CDK2). The design, synthesis, and testing of a series of 1-isopropyl-4-aminobenzyl-6-ether-linked benzimidazoles is presented. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.11.022