tert-butyl 4-(1H-benzimidazol-2-ylmethyl)piperidine-1-carboxylate | 1193783-79-7

• 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-(1H-benzimidazol-2-ylmethyl)piperidine-1-carboxylate
• 英文别名: tert-butyl 4-[(1H-1,3-benzodiazol-2-yl)methyl]piperidine-1-carboxylate
• CAS: 1193783-79-7
• 化学式: C₁₈H₂₅N₃O₂
• 分子量: 315.415
• InChiKey: PLVBGNQFSWMSHA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  58.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tert-butyl 4-(1H-benzimidazol-2-ylmethyl)piperidine-1-carboxylate 在 盐酸 作用下， 以 乙醚 为溶剂， 以100%的产率得到2-(4-piperidinylmethyl)-1H-benzimidazole
  参考文献：
  名称：

  A new class of 5-HT2B antagonists possesses favorable potency, selectivity, and rat pharmacokinetic properties

  摘要：

  We have been exploring the potential of 5-HT2B antagonists as a therapy for chronic heart failure. To assess the potential of this therapeutic approach, we sought compounds possessing the following attributes: (a) potent and selective antagonism of the 5-HT2B receptor, (b) low impact of serum proteins on potency, and (c) desirable pharmacokinetic properties. This Letter describes our investigation of a biphenyl benzimidazole class of compounds that resulted in 5-HT2B antagonists possessing the above attributes. Improving potency in a human serum albumin shift assay proved to be the most significant SAR discovery. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.02.126
• 作为产物：
  描述：

  邻苯二胺 、 1-叔丁氧羰基-4-哌啶乙酸 在 吡啶 、 亚磷酸三苯酯 作用下， 反应 18.0h， 生成 tert-butyl 4-(1H-benzimidazol-2-ylmethyl)piperidine-1-carboxylate
  参考文献：
  名称：

  A new class of 5-HT2B antagonists possesses favorable potency, selectivity, and rat pharmacokinetic properties

  摘要：

  We have been exploring the potential of 5-HT2B antagonists as a therapy for chronic heart failure. To assess the potential of this therapeutic approach, we sought compounds possessing the following attributes: (a) potent and selective antagonism of the 5-HT2B receptor, (b) low impact of serum proteins on potency, and (c) desirable pharmacokinetic properties. This Letter describes our investigation of a biphenyl benzimidazole class of compounds that resulted in 5-HT2B antagonists possessing the above attributes. Improving potency in a human serum albumin shift assay proved to be the most significant SAR discovery. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.02.126

文献信息

• A new class of 5-HT2B antagonists possesses favorable potency, selectivity, and rat pharmacokinetic properties
  作者：Neil Moss、Younggi Choi、Derek Cogan、Adam Flegg、Andreas Kahrs、Pui Loke、Orietta Meyn、Raj Nagaraja、Spencer Napier、Ashley Parker、J. Thomas Peterson、Philip Ramsden、Christopher Sarko、Donna Skow、Josh Tomlinson、Heather Tye、Mark Whitaker

  DOI：10.1016/j.bmcl.2009.02.126

  日期：2009.4

  We have been exploring the potential of 5-HT2B antagonists as a therapy for chronic heart failure. To assess the potential of this therapeutic approach, we sought compounds possessing the following attributes: (a) potent and selective antagonism of the 5-HT2B receptor, (b) low impact of serum proteins on potency, and (c) desirable pharmacokinetic properties. This Letter describes our investigation of a biphenyl benzimidazole class of compounds that resulted in 5-HT2B antagonists possessing the above attributes. Improving potency in a human serum albumin shift assay proved to be the most significant SAR discovery. (C) 2009 Elsevier Ltd. All rights reserved.