N-(4-morpholin-4-ylphenyl)-2-(4-nitrophenoxy)acetamide | 304675-29-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 恶嗪烷类
• 英文名称: N-(4-morpholin-4-ylphenyl)-2-(4-nitrophenoxy)acetamide
• 英文别名: Cambridge id 5624718
• CAS: 304675-29-4
• 化学式: C₁₈H₁₉N₃O₅
• mdl: MFCD01071722
• 分子量: 357.366
• InChiKey: XMBBWSBKBTZWCL-UHFFFAOYSA-N

物化性质

• 熔点：
  170-172 °C(Solv: ethyl acetate (141-78-6); ethyl ether (60-29-7))
• 沸点：
  650.8±55.0 °C(Predicted)
• 密度：
  1.343±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  96.6
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-(4-morpholin-4-ylphenyl)-2-(4-nitrophenoxy)acetamide 在 palladium on activated charcoal sodium tetrahydroborate 作用下， 以 甲醇 、 水 为溶剂， 以72%的产率得到2-(4-aminophenoxy)-N-(4-morpholinophenyl)acetamide
  参考文献：
  名称：

  N6-[(Hetero)aryl/(cyclo)alkyl-carbamoyl-methoxy-phenyl]-(2-chloro)-5′-N-ethylcarboxamido-adenosines: The first example of adenosine-related structures with potent agonist activity at the human A2B adenosine receptor

  摘要：

  A new series of N-6-[(hetero)aryl/(cyclo)alkyl-carbamoyl-methoxy-phenyl]-(2-chloro)-5'-N-ethylcarboxamido-adenosines (24-43) has been synthesised and tested in binding assays at hA(1), hA(2A) and hA(3) adenosine receptors, and in a functional assay at the hA(2B) subtype. The examined compounds displayed high potency in activating A(2B) receptors with good selectivity versus A(2A) subtypes. The introduction of an unsubstituted 4-[(phenylcarbamoyl)-methoxyl-phenyI chain at the N-6 position of 5'-N-ethylcarboxamido -adenosine led us to the recognition of compound 24 as a full agonist displaying the highest efficacy of the series (EC50 hA(2B) = 7.3 nM). These compounds represent the first report about adenosine-related structures capable of activating hA2B subtype in the low nanomolar range. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.01.055
• 作为产物：
  描述：

  4-(4-吗啉基)苯胺 在 potassium carbonate 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 16.0h， 生成 N-(4-morpholin-4-ylphenyl)-2-(4-nitrophenoxy)acetamide
  参考文献：
  名称：

  N6-[(Hetero)aryl/(cyclo)alkyl-carbamoyl-methoxy-phenyl]-(2-chloro)-5′-N-ethylcarboxamido-adenosines: The first example of adenosine-related structures with potent agonist activity at the human A2B adenosine receptor

  摘要：

  A new series of N-6-[(hetero)aryl/(cyclo)alkyl-carbamoyl-methoxy-phenyl]-(2-chloro)-5'-N-ethylcarboxamido-adenosines (24-43) has been synthesised and tested in binding assays at hA(1), hA(2A) and hA(3) adenosine receptors, and in a functional assay at the hA(2B) subtype. The examined compounds displayed high potency in activating A(2B) receptors with good selectivity versus A(2A) subtypes. The introduction of an unsubstituted 4-[(phenylcarbamoyl)-methoxyl-phenyI chain at the N-6 position of 5'-N-ethylcarboxamido -adenosine led us to the recognition of compound 24 as a full agonist displaying the highest efficacy of the series (EC50 hA(2B) = 7.3 nM). These compounds represent the first report about adenosine-related structures capable of activating hA2B subtype in the low nanomolar range. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.01.055

文献信息

• N6-[(Hetero)aryl/(cyclo)alkyl-carbamoyl-methoxy-phenyl]-(2-chloro)-5′-N-ethylcarboxamido-adenosines: The first example of adenosine-related structures with potent agonist activity at the human A2B adenosine receptor
  作者：Pier Giovanni Baraldi、Delia Preti、Mojgan Aghazadeh Tabrizi、Francesca Fruttarolo、Giulia Saponaro、Stefania Baraldi、Romeo Romagnoli、Allan R. Moorman、Stefania Gessi、Katia Varani、Pier Andrea Borea

  DOI：10.1016/j.bmc.2007.01.055

  日期：2007.4

  A new series of N-6-[(hetero)aryl/(cyclo)alkyl-carbamoyl-methoxy-phenyl]-(2-chloro)-5'-N-ethylcarboxamido-adenosines (24-43) has been synthesised and tested in binding assays at hA(1), hA(2A) and hA(3) adenosine receptors, and in a functional assay at the hA(2B) subtype. The examined compounds displayed high potency in activating A(2B) receptors with good selectivity versus A(2A) subtypes. The introduction of an unsubstituted 4-[(phenylcarbamoyl)-methoxyl-phenyI chain at the N-6 position of 5'-N-ethylcarboxamido -adenosine led us to the recognition of compound 24 as a full agonist displaying the highest efficacy of the series (EC50 hA(2B) = 7.3 nM). These compounds represent the first report about adenosine-related structures capable of activating hA2B subtype in the low nanomolar range. (c) 2007 Elsevier Ltd. All rights reserved.