(R)-tert-butyl 3-(4-((1H-benzo[d]imidazol-1-yl)methyl)benzamido)-pyrrolidine-1-carboxylate | 1087328-32-2

• 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: (R)-tert-butyl 3-(4-((1H-benzo[d]imidazol-1-yl)methyl)benzamido)-pyrrolidine-1-carboxylate
• 英文别名: tert-butyl (3R)-3-[[4-(benzimidazol-1-ylmethyl)benzoyl]amino]pyrrolidine-1-carboxylate
• CAS: 1087328-32-2
• 化学式: C₂₄H₂₈N₄O₃
• 分子量: 420.511
• InChiKey: RZWVUWIZXZQVPK-LJQANCHMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  76.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-tert-butyl 3-(4-((1H-benzo[d]imidazol-1-yl)methyl)benzamido)-pyrrolidine-1-carboxylate 在 三乙酰氧基硼氢化钠 、 sodium hydride 、 溶剂黄146 、 三氟乙酸 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 54.0h， 生成 4-(1H-benzimidazol-1-ylmethyl)-N-[(3R)-1-isopropylpyrrolidin-3-yl]-N-methylbenzamide
  参考文献：
  名称：

  Pyrrolidin-3-yl-N-methylbenzamides as potent histamine 3 receptor antagonists

  摘要：

  On the basis of the previously reported benzimidazole 1,3'-bipyrrolidine benzamides (1), a series of related pyrrolidin-3-yl-N-methylbenzamides were synthesized and evaluated as H(3) receptor antagonists. In particular, compound 32 exhibits potent H(3) receptor binding affinity, improved pharmaceutical properties and a favorable in vivo profile. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.07.061
• 作为产物：
  描述：

  methyl 4-((1H-benzo[d]imidazol-1-yl)methyl)benzoate 在 N-甲基吗啉 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 lithium hydroxide 作用下， 反应 20.0h， 生成 (R)-tert-butyl 3-(4-((1H-benzo[d]imidazol-1-yl)methyl)benzamido)-pyrrolidine-1-carboxylate
  参考文献：
  名称：

  Pyrrolidin-3-yl-N-methylbenzamides as potent histamine 3 receptor antagonists

  摘要：

  On the basis of the previously reported benzimidazole 1,3'-bipyrrolidine benzamides (1), a series of related pyrrolidin-3-yl-N-methylbenzamides were synthesized and evaluated as H(3) receptor antagonists. In particular, compound 32 exhibits potent H(3) receptor binding affinity, improved pharmaceutical properties and a favorable in vivo profile. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.07.061

文献信息

• AZACYCLYLBENZAMIDE DERIVATIVES AS HISTAMINE-3 ANTAGONISTS
  申请人：Zhou Dahui

  公开号：US20080293771A1

  公开（公告）日：2008-11-27

  The present invention provides a compound of formula I and the use thereof for the treatment of a central nervous system disorder related to or affected by the histamine-3 receptor

  本发明提供了一种I式化合物及其用于治疗与或受到组胺-3受体相关的中枢神经系统疾病的用途。
• Pyrrolidin-3-yl-N-methylbenzamides as potent histamine 3 receptor antagonists
  作者：Dahui Zhou、Jonathan L. Gross、Jean Y. Sze、Adedayo B. Adedoyin、Mark Bowlby、Li Di、Brian J. Platt、Guoming Zhang、Nicholas Brandon、Thomas A. Comery、Albert J. Robichaud

  DOI：10.1016/j.bmcl.2011.07.061

  日期：2011.10

  On the basis of the previously reported benzimidazole 1,3'-bipyrrolidine benzamides (1), a series of related pyrrolidin-3-yl-N-methylbenzamides were synthesized and evaluated as H(3) receptor antagonists. In particular, compound 32 exhibits potent H(3) receptor binding affinity, improved pharmaceutical properties and a favorable in vivo profile. (C) 2011 Elsevier Ltd. All rights reserved.