tert-butyl 3-(1-(2-phenoxyethyl)-1H-benzo[d]imidazol-2-yl)piperidine-1-carboxylate | 1229000-36-5

• 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 3-(1-(2-phenoxyethyl)-1H-benzo[d]imidazol-2-yl)piperidine-1-carboxylate
• CAS: 1229000-36-5
• 化学式: C₂₅H₃₁N₃O₃
• 分子量: 421.539
• InChiKey: BEYOHSNGVYZKMH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.23
• 重原子数：
  31.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  56.59
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  tert-butyl 3-(1-(2-phenoxyethyl)-1H-benzo[d]imidazol-2-yl)piperidine-1-carboxylate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 1-(2-Phenoxyethyl)-2-piperidin-3-ylbenzimidazole
  参考文献：
  名称：

  The discovery and structure–activity relationships of 2-(piperidin-3-yl)-1H-benzimidazoles as selective, CNS penetrating H1-antihistamines for insomnia

  摘要：

  A series of 2-(3-aminopiperidine)-benzimidazoles were identified as selective H-1-antihistamines for evaluation as potential sedative hypnotics. Representative compounds showed improved hERG selectivity over a previously identified 2-aminobenzimidazole series. While hERG activity could be modulated via manipulation of the benzimidazole N1 substituent, this approach led to a reduction in CNS exposure for the more selective compounds. One example, 9q, retained a suitable selectivity profile with CNS exposure equivalent to known centrally active H-1-antihistamines. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.03.027
• 作为产物：
  描述：

  邻苯二胺 在 potassium carbonate 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 tert-butyl 3-(1-(2-phenoxyethyl)-1H-benzo[d]imidazol-2-yl)piperidine-1-carboxylate
  参考文献：
  名称：

  Lead optimization of 2-(piperidin-3-yl)-1H-benzimidazoles: Identification of 2-morpholin- and 2-thiomorpholin-2-yl-1H-benzimidazoles as selective and CNS penetrating H1-antihistamines for insomnia

  摘要：

  The structure-activity relationships of 2-(piperidin-3-yl)-1H-benzimidazoles, 2-morpholine and 2-thiomorpholin-2-yl-1H-benzimidazoles are described. In the lead optimization process, the pK(a) and/or logP of benzimidazole analogs were reduced either by attachment of polar substituents to the piperidine nitrogen or incorporation of heteroatoms into the piperidine heterocycle. Compounds 9a and 9b in the morpholine series and 10g in the thiomorpholine series demonstrated improved selectivity and CNS profiles compared to lead compound 2 and these are potential candidates for evaluation as sedative hypnotics. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.10.115