1-[(4-fluorophenyl)methyl]-2-[(3R)-piperidin-3-yl]benzimidazole | 1248737-39-4

• 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: 1-[(4-fluorophenyl)methyl]-2-[(3R)-piperidin-3-yl]benzimidazole
• CAS: 1248737-39-4
• 化学式: C₁₉H₂₀FN₃
• 分子量: 309.386
• InChiKey: VIEHHRQCEMIKCL-OAHLLOKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  29.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-BOC-哌啶-3-羧酸 在 potassium carbonate 、 三氟乙酸 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 1-[(4-fluorophenyl)methyl]-2-[(3R)-piperidin-3-yl]benzimidazole
  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

文献信息

• 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
  作者：Satheesh Babu Ravula、Jinghua Yu、Joe A. Tran、Melissa Arellano、Fabio C. Tucci、Wilna J. Moree、Bin-Feng Li、Robert E. Petroski、Jianyun Wen、Siobhan Malany、Samuel R.J. Hoare、Ajay Madan、Paul D. Crowe、Graham Beaton

  DOI：10.1016/j.bmcl.2011.10.115

  日期：2012.1

  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.