5-[(1R,3R)-3-(2,3-Dihydro-benzofuran-4-yl)-2,2-dimethyl-cyclopropyl]-1H-imidazol-2-ylamine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 香豆素
• 英文名称: 5-[(1R,3R)-3-(2,3-Dihydro-benzofuran-4-yl)-2,2-dimethyl-cyclopropyl]-1H-imidazol-2-ylamine
• 英文别名: 5-[(1R,3R)-3-(2,3-dihydro-1-benzofuran-4-yl)-2,2-dimethylcyclopropyl]-1H-imidazol-2-amine
• 化学式: C₁₆H₁₉N₃O
• 分子量: 269.346
• InChiKey: MDSBMBXDSJELPF-ZIAGYGMSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  63.9
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (1R,3R)-3-(2,3-dihydro-4-benzofuranyl)-2,2-dimethylcyclopropanecarboxylic acid 在 N-溴代丁二酰亚胺(NBS) 、 硫酸 、 N,N'-羰基二咪唑 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 5-[(1R,3R)-3-(2,3-Dihydro-benzofuran-4-yl)-2,2-dimethyl-cyclopropyl]-1H-imidazol-2-ylamine
  参考文献：
  名称：

  Aminoimidazoles as bioisosteres of acylguanidines: novel, potent, selective and orally bioavailable inhibitors of the sodium hydrogen exchanger isoform-1

  摘要：

  dInhibition of the sodium hydrogen exchanger isoform-1 (NHE-1) has been shown to limit damage to the myocardium under ischemic conditions in animals. While most known NHE-1 inhibitors are acylguanidines, this report describes the design and synthesis of a series of heterocyclic inhibitors of NHE-1 including aminoimidazoles with undiminished in vitro activity and oral bioavailability. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.09.066

文献信息

• US7326705B2
  申请人：——

  公开号：US7326705B2

  公开（公告）日：2008-02-05
• Aminoimidazoles as bioisosteres of acylguanidines: novel, potent, selective and orally bioavailable inhibitors of the sodium hydrogen exchanger isoform-1
  作者：Saleem Ahmad、Khehyong Ngu、Donald W Combs、Shung C Wu、David S Weinstein、Wen Liu、Bang-Chi Chen、Gamini Chandrasena、Charles R Dorso、Mark Kirby、Karnail S Atwal

  DOI：10.1016/j.bmcl.2003.09.066

  日期：2004.1

  dInhibition of the sodium hydrogen exchanger isoform-1 (NHE-1) has been shown to limit damage to the myocardium under ischemic conditions in animals. While most known NHE-1 inhibitors are acylguanidines, this report describes the design and synthesis of a series of heterocyclic inhibitors of NHE-1 including aminoimidazoles with undiminished in vitro activity and oral bioavailability. (C) 2003 Elsevier Ltd. All rights reserved.