1-[4-(2-Amino-ethyl)-1-(2-methoxy-ethoxymethyl)-1H-imidazol-2-yl]-3,3-diphenyl-propan-1-one | 876404-40-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-[4-(2-Amino-ethyl)-1-(2-methoxy-ethoxymethyl)-1H-imidazol-2-yl]-3,3-diphenyl-propan-1-one
• 英文别名: 1-[4-(2-Aminoethyl)-1-(2-methoxyethoxymethyl)imidazol-2-yl]-3,3-diphenylpropan-1-one
• CAS: 876404-40-9
• 化学式: C₂₄H₂₉N₃O₃
• 分子量: 407.513
• InChiKey: LJVBGFTYHFVYRG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  30
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  79.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-[4-(2-Amino-ethyl)-1-(2-methoxy-ethoxymethyl)-1H-imidazol-2-yl]-3,3-diphenyl-propan-1-one 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 1.5h， 以97%的产率得到1-[4-(2-Amino-ethyl)-1H-imidazol-2-yl]-3,3-diphenyl-propan-1-one; compound with GENERIC INORGANIC NEUTRAL COMPONENT
  参考文献：
  名称：

  Side-chain modified analogues of histaprodifen: Asymmetric synthesis and histamine H1-receptor activity

  摘要：

  New analogues of histaprodifen with polar side chains have been stereo selectively synthesized and evaluated as histamine H-1-receptor agonists. As a key transformation the asymmetric aminohydroxylation has been used, which was successfully realized for the first time on an imidazolyl derivative. While all chiral analogues proved to be weak H-1-receptor antagonists, an achiral keto derivative of histaprodifen turned out to be the first 2-acylated histamine congener displaying partial H-1-receptor agonism (relative potency 12%). (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.10.030
• 作为产物：
  描述：

  {2-[2-(3,3-Diphenyl-propionyl)-1-(2-methoxy-ethoxymethyl)-1H-imidazol-4-yl]-ethyl}-carbamic acid benzyl ester 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 16.0h， 以86%的产率得到1-[4-(2-Amino-ethyl)-1-(2-methoxy-ethoxymethyl)-1H-imidazol-2-yl]-3,3-diphenyl-propan-1-one
  参考文献：
  名称：

  Side-chain modified analogues of histaprodifen: Asymmetric synthesis and histamine H1-receptor activity

  摘要：

  New analogues of histaprodifen with polar side chains have been stereo selectively synthesized and evaluated as histamine H-1-receptor agonists. As a key transformation the asymmetric aminohydroxylation has been used, which was successfully realized for the first time on an imidazolyl derivative. While all chiral analogues proved to be weak H-1-receptor antagonists, an achiral keto derivative of histaprodifen turned out to be the first 2-acylated histamine congener displaying partial H-1-receptor agonism (relative potency 12%). (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.10.030

文献信息

• Side-chain modified analogues of histaprodifen: Asymmetric synthesis and histamine H1-receptor activity
  作者：Rameshwar Patil、Sigurd Elz、Oliver Reiser

  DOI：10.1016/j.bmcl.2005.10.030

  日期：2006.2

  New analogues of histaprodifen with polar side chains have been stereo selectively synthesized and evaluated as histamine H-1-receptor agonists. As a key transformation the asymmetric aminohydroxylation has been used, which was successfully realized for the first time on an imidazolyl derivative. While all chiral analogues proved to be weak H-1-receptor antagonists, an achiral keto derivative of histaprodifen turned out to be the first 2-acylated histamine congener displaying partial H-1-receptor agonism (relative potency 12%). (c) 2005 Elsevier Ltd. All rights reserved.