3-{[4-(1H-benzimidazol-2-yl)piperidin-1-yl]carbonyl}-6-phenylpyridin-2(1H)-one | 1159096-80-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 3-{[4-(1H-benzimidazol-2-yl)piperidin-1-yl]carbonyl}-6-phenylpyridin-2(1H)-one
• 英文别名: 3-(4-(1H-benzo[d]imidazol-2-yl)piperidine-1-carbonyl)-6-phenylpyridin-2(1H)-one；3-[4-(1H-benzimidazol-2-yl)piperidine-1-carbonyl]-6-phenyl-1H-pyridin-2-one
• CAS: 1159096-80-6
• 化学式: C₂₄H₂₂N₄O₂
• 分子量: 398.464
• InChiKey: IVLWBLYHPAQTOQ-UHFFFAOYSA-N

物化性质

• 沸点：
  787.6±60.0 °C(predicted)
• 密度：
  1.326±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  30
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  78.1
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-氧代-6-苯基-1,2-二氢-3-吡啶羧酸 、 2-(4-哌啶)-1H-苯并咪唑 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 生成 3-{[4-(1H-benzimidazol-2-yl)piperidin-1-yl]carbonyl}-6-phenylpyridin-2(1H)-one
  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

• [EN] SEROTONIN 5-HT2B RECEPTOR INHIBITORS<br/>[FR] INHIBITEURS DU RÉCEPTEUR 5-HT2B DE LA SÉROTONINE
  申请人：BOEHRINGER INGELHEIM INT

  公开号：WO2010080357A1

  公开（公告）日：2010-07-15

  Disclosed are Serotonin 5-HT2B receptor inhibitors of the formula I. Also disclosed are methods of making and methods of using these compounds.

  揭示了式I的5-HT2B受体拮抗剂。还公开了制备这些化合物的方法和使用这些化合物的方法。
• Serotonin 5-HT2B Receptor Inhibitors
  申请人：Cogan Derek

  公开号：US20110269742A1

  公开（公告）日：2011-11-03

  Disclosed are Serotonin 5-HT2B receptor inhibitors of the formula I. Also disclosed are methods of making and methods of using these compounds.

  本发明涉及公开了化学式I的血清素5-HT2B受体抑制剂。还公开了制备这些化合物的方法和使用这些化合物的方法。
• US8609696B2
  申请人：——

  公开号：US8609696B2

  公开（公告）日：2013-12-17
• 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.