1-(2-Methoxyethyl)-3-[1-(piperidine-4-carbonyl)piperidin-4-yl]benzimidazol-2-one | 633312-94-4

• 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-(2-Methoxyethyl)-3-[1-(piperidine-4-carbonyl)piperidin-4-yl]benzimidazol-2-one
• CAS: 633312-94-4
• 化学式: C₂₁H₃₀N₄O₃
• 分子量: 386.494
• InChiKey: TZYDRZRKVURJCD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  65.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-吡啶甲醛 、 1-(2-Methoxyethyl)-3-[1-(piperidine-4-carbonyl)piperidin-4-yl]benzimidazol-2-one 在 三乙酰氧基硼氢化钠 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 生成 1-(2-methoxyethyl)-3-(1-(1-(pyridin-4-ylmethyl)piperidine-4-carbonyl)piperidin-4-yl)-1H-benzo[d]imidazol-2(3H)-one
  参考文献：
  名称：

  The synthesis and structure–activity relationship of 4-benzimidazolyl-piperidinylcarbonyl-piperidine analogs as histamine H3 antagonists

  摘要：

  A structure-activity relationship study of the lead piperazinylcarbonylpiperidine compound 3 resulted in the identification of 4-benzimidazolyl-piperidinylcarbonyl-piperidine 6h as a histamine-3 (H-3) receptor antagonist. Additional optimization of 6h led to the identification of compounds 11i-k with Ki <= 0.5 nM and good in vivo activity. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.07.052
• 作为产物：
  描述：

  在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 以100%的产率得到1-(2-Methoxyethyl)-3-[1-(piperidine-4-carbonyl)piperidin-4-yl]benzimidazol-2-one
  参考文献：
  名称：

  The synthesis and structure–activity relationship of 4-benzimidazolyl-piperidinylcarbonyl-piperidine analogs as histamine H3 antagonists

  摘要：

  A structure-activity relationship study of the lead piperazinylcarbonylpiperidine compound 3 resulted in the identification of 4-benzimidazolyl-piperidinylcarbonyl-piperidine 6h as a histamine-3 (H-3) receptor antagonist. Additional optimization of 6h led to the identification of compounds 11i-k with Ki <= 0.5 nM and good in vivo activity. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.07.052

文献信息

• [EN] 1-(4-PIPERIDINYL) BENZIMIDAZOLONES AS HISTAMINE H3 ANTAGONISTS<br/>[FR] 1-(4-PIPERIDINYL) BENZIMIDAZOLONES UTILISES EN TANT QU'ANTAGONISTES DU RECEPTEUR H3 DE L'HISTAMINE
  申请人：SCHERING CORP

  公开号：WO2003103669A1

  公开（公告）日：2003-12-18

  Disclosed are histamine H3 antagonists of the formula (I) wherein R1 is benzimidazolone derivative, M1 and M2 are optionally substituted carbon or nitrogen, R2 includes optionally substituted aryl or heteroaryl, and the remaining variables are as defined in the specification. Also disclosed are pharmaceutical compositions comprising the compounds of formula (I). Also disclosed are methods of treating various diseases or conditions, such as, for example, allergy, allergy-induced airway responses, and congestion (e.g., nasal congestion) using the compounds of Formula (I). Also disclosed are methods of treating various diseases or conditions, such as, for example, allergy, allergy-induced airway responses, and congestion (e.g., nasal congestion) using the compounds of formula (I) in combination with a H1 receptor antagonist.

  揭示了公式（I）中的组胺H3拮抗剂，其中R1是苯并咪唑酮衍生物，M1和M2是可选择地取代的碳或氮，R2包括可选择地取代的芳基或杂环基，其余变量如规范中所定义。还揭示了包括公式（I）化合物的药物组合物。还揭示了使用公式（I）化合物治疗各种疾病或症状的方法，例如过敏、过敏引起的气道反应和充血（例如，鼻塞）的方法。还揭示了使用公式（I）化合物与H1受体拮抗剂结合治疗各种疾病或症状的方法，例如过敏、过敏引起的气道反应和充血（例如，鼻塞）。
• US7220735B2
  申请人：——

  公开号：US7220735B2

  公开（公告）日：2007-05-22
• The synthesis and structure–activity relationship of 4-benzimidazolyl-piperidinylcarbonyl-piperidine analogs as histamine H3 antagonists
  作者：Pauline C. Ting、Joe F. Lee、Margaret M. Albanese、Jie Wu、Robert Aslanian、Leonard Favreau、Cymbelene Nardo、Walter A. Korfmacher、Robert E. West、Shirley M. Williams、John C. Anthes、Maria A. Rivelli、Michel R. Corboz、John A. Hey

  DOI：10.1016/j.bmcl.2010.07.052

  日期：2010.9

  A structure-activity relationship study of the lead piperazinylcarbonylpiperidine compound 3 resulted in the identification of 4-benzimidazolyl-piperidinylcarbonyl-piperidine 6h as a histamine-3 (H-3) receptor antagonist. Additional optimization of 6h led to the identification of compounds 11i-k with Ki <= 0.5 nM and good in vivo activity. (C) 2010 Elsevier Ltd. All rights reserved.