2-(4-氨基苯氧基)-N-环己基乙酰胺 | 100875-61-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 2-(4-氨基苯氧基)-N-环己基乙酰胺
• 英文名称: 2-(4-aminophenoxy)-N-cyclohexylacetamide
• 英文别名: (4-amino-phenoxy)-acetic acid cyclohexylamide；(4-Amino-phenoxy)-essigsaeure-cyclohexylamid
• CAS: 100875-61-4
• 化学式: C₁₄H₂₀N₂O₂
• 分子量: 248.325
• InChiKey: RAFATNZSFWKIKW-UHFFFAOYSA-N

物化性质

• 熔点：
  87 °C(Solv: ethanol (64-17-5))
• 沸点：
  501.0±33.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  64.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(4-氨基苯氧基)-N-环己基乙酰胺 在 三乙胺 、 三氟乙酸 作用下， 以 乙醇 、 水 为溶剂， 反应 15.0h， 生成 (2S,3S,4R,5R)-5-(2-chloro-6-(4-(2-(cyclohexylamino)-2-oxoethoxy)phenylamino)-9H-purin-9-yl)-N-ethyl-3,4-dihydroxy-tetrahydrofuran-2-carboxamide
  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：

  2-氯-n-环己基-乙酰胺 在 palladium on activated charcoal sodium tetrahydroborate 、 potassium carbonate 作用下， 以 甲醇 、 水 、 丙酮 为溶剂， 反应 12.0h， 生成 2-(4-氨基苯氧基)-N-环己基乙酰胺
  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

• Shridhar, D. R.; Rao, K. Srinivasa; Singh, A. N., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1986, vol. 25, p. 1277 - 1280
  作者：Shridhar, D. R.、Rao, K. Srinivasa、Singh, A. N.、Rastogi, K.、Jain, M. L.

  DOI：——

  日期：——
• SHRIDHAR, D. R.;RAO, K. SRINIVASA;SINGH, A. N.;RASTOGI, K.;JAIN, M. L., INDIAN J. CHEM., 25,(1986) N 12, 1277-1280
  作者：SHRIDHAR, D. R.、RAO, K. SRINIVASA、SINGH, A. N.、RASTOGI, K.、JAIN, M. L.

  DOI：——

  日期：——
• 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.