1-(1H-咪唑-1-基)-2-(3-硝基苯氧基)乙烷-1-酮 | 1025941-26-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1-(1H-咪唑-1-基)-2-(3-硝基苯氧基)乙烷-1-酮
• 英文名称: 1-Imidazol-1-yl-2-(3-nitrophenoxy)ethanone
• CAS: 1025941-26-7
• 化学式: C₁₁H₉N₃O₄
• 分子量: 247.21
• InChiKey: FOKPYESOHUBROG-UHFFFAOYSA-N

物化性质

• 沸点：
  477.5±51.0 °C(Predicted)
• 密度：
  1.39±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  89.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(1H-咪唑-1-基)-2-(3-硝基苯氧基)乙烷-1-酮 在 palladium on activated charcoal 氨 、 氢气 作用下， 以 四氢呋喃 、 甲醇 、 乙酸乙酯 为溶剂， 反应 7.0h， 生成 (3-aminophenoxy)acetamide
  参考文献：
  名称：

  Discovery of 1,5-Benzodiazepines with Peripheral Cholecystokinin (CCK-A) Receptor Agonist Activity (II):  Optimization of the C3 Amino Substituent

  摘要：

  Analogs of the previously reported 1,5-benzodiazepine peripheral cholecystokinin (CCK-A) receptor agonist 1 were prepared which explore substitution and/or replacement of the C-3 phenyl urea moiety. Agonist efficacy on the isolated guinea pig gallbladder (GPGB) was retained with a variety of substituted ureas and amide analogs. Three compounds were identified which were orally active in the mouse gallbladder emptying assay (MGBE). The 2-indolamide (52) and N-(carboxymethyl)-2-indolamide (54) derivatives had improved affinity for the human CCK-A receptor but reduced agonist efficacy on the GPGB. Neither indolamide was orally active in a rat feeding assay. In contrast, the (3-carboxyphenyl)urea derivative (29, GW7854) had moderately increased affinity for the human CCK-B receptor but was a potent full agonist on the GPGB and was orally active in both the MGBE and rat feeding assays. GW7854 was a full agonist (EC(50) = 60 nM) for calcium mobilization on CHO K1 cells expressing hCCK-A receptors and a potent antagonist; of CCK-8 (pA(2) = 9.1) on CHO K1 cells expressing hCCK-B receptors. GW7854 is a potent mixed CCK-A agonist/CCK-B antagonist which is orally active in two in vivo models of CCK-A-mediated agonist activity.

  DOI：

  10.1021/jm9601664
• 作为产物：
  描述：

  tert-butyl 3-nitrophenoxyacetate 在 盐酸 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 反应 5.0h， 生成 1-(1H-咪唑-1-基)-2-(3-硝基苯氧基)乙烷-1-酮
  参考文献：
  名称：

  Discovery of 1,5-Benzodiazepines with Peripheral Cholecystokinin (CCK-A) Receptor Agonist Activity (II):  Optimization of the C3 Amino Substituent

  摘要：

  Analogs of the previously reported 1,5-benzodiazepine peripheral cholecystokinin (CCK-A) receptor agonist 1 were prepared which explore substitution and/or replacement of the C-3 phenyl urea moiety. Agonist efficacy on the isolated guinea pig gallbladder (GPGB) was retained with a variety of substituted ureas and amide analogs. Three compounds were identified which were orally active in the mouse gallbladder emptying assay (MGBE). The 2-indolamide (52) and N-(carboxymethyl)-2-indolamide (54) derivatives had improved affinity for the human CCK-A receptor but reduced agonist efficacy on the GPGB. Neither indolamide was orally active in a rat feeding assay. In contrast, the (3-carboxyphenyl)urea derivative (29, GW7854) had moderately increased affinity for the human CCK-B receptor but was a potent full agonist on the GPGB and was orally active in both the MGBE and rat feeding assays. GW7854 was a full agonist (EC(50) = 60 nM) for calcium mobilization on CHO K1 cells expressing hCCK-A receptors and a potent antagonist; of CCK-8 (pA(2) = 9.1) on CHO K1 cells expressing hCCK-B receptors. GW7854 is a potent mixed CCK-A agonist/CCK-B antagonist which is orally active in two in vivo models of CCK-A-mediated agonist activity.

  DOI：

  10.1021/jm9601664

文献信息

• Discovery of 1,5-Benzodiazepines with Peripheral Cholecystokinin (CCK-A) Receptor Agonist Activity (II):  Optimization of the C3 Amino Substituent
  作者：Gavin C. Hirst、Christopher Aquino、Lawrence Birkemo、Dallas K. Croom、Milana Dezube、Robert W. Dougherty,、Gregory N. Ervin、Mary K. Grizzle、Brad Henke、Michael K. James、Michael F. Johnson、Tanya Momtahen、Kennedy L. Queen、Ronald G. Sherrill、Jerzy Szewczyk、Timothy M. Willson、Elizabeth E. Sugg

  DOI：10.1021/jm9601664

  日期：1996.1.1

  Analogs of the previously reported 1,5-benzodiazepine peripheral cholecystokinin (CCK-A) receptor agonist 1 were prepared which explore substitution and/or replacement of the C-3 phenyl urea moiety. Agonist efficacy on the isolated guinea pig gallbladder (GPGB) was retained with a variety of substituted ureas and amide analogs. Three compounds were identified which were orally active in the mouse gallbladder emptying assay (MGBE). The 2-indolamide (52) and N-(carboxymethyl)-2-indolamide (54) derivatives had improved affinity for the human CCK-A receptor but reduced agonist efficacy on the GPGB. Neither indolamide was orally active in a rat feeding assay. In contrast, the (3-carboxyphenyl)urea derivative (29, GW7854) had moderately increased affinity for the human CCK-B receptor but was a potent full agonist on the GPGB and was orally active in both the MGBE and rat feeding assays. GW7854 was a full agonist (EC(50) = 60 nM) for calcium mobilization on CHO K1 cells expressing hCCK-A receptors and a potent antagonist; of CCK-8 (pA(2) = 9.1) on CHO K1 cells expressing hCCK-B receptors. GW7854 is a potent mixed CCK-A agonist/CCK-B antagonist which is orally active in two in vivo models of CCK-A-mediated agonist activity.