1-deoxy-1-[6-(4-{[2-(trifluoromethyl)phenylcarbamoyl]methoxy}phenylamino)-9H-purin-9-yl]-N-ethyl-2,3-O-(1-methylethylidene)-β-D-ribofuranuronamide | 936632-71-2

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: 1-deoxy-1-[6-(4-{[2-(trifluoromethyl)phenylcarbamoyl]methoxy}phenylamino)-9H-purin-9-yl]-N-ethyl-2,3-O-(1-methylethylidene)-β-D-ribofuranuronamide
• CAS: 936632-71-2
• 化学式: C₃₀H₃₀F₃N₇O₆
• 分子量: 641.607
• InChiKey: CAQHRRVORKTYPL-GFXAMXPBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.16
• 重原子数：
  46.0
• 可旋转键数：
  9.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  150.75
• 氢给体数：
  3.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  1-deoxy-1-[6-(4-{[2-(trifluoromethyl)phenylcarbamoyl]methoxy}phenylamino)-9H-purin-9-yl]-N-ethyl-2,3-O-(1-methylethylidene)-β-D-ribofuranuronamide 在 三氟乙酸 作用下， 以 水 为溶剂， 反应 3.0h， 以55%的产率得到(2S,3S,4R,5R)-N-ethyl-3,4-dihydroxy-5-[6-[4-[2-oxo-2-[2-(trifluoromethyl)anilino]ethoxy]anilino]purin-9-yl]oxolane-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：

  邻氨基三氟甲苯 在 palladium on activated charcoal sodium tetrahydroborate 、 potassium carbonate 、 三乙胺 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 28.0h， 生成 1-deoxy-1-[6-(4-{[2-(trifluoromethyl)phenylcarbamoyl]methoxy}phenylamino)-9H-purin-9-yl]-N-ethyl-2,3-O-(1-methylethylidene)-β-D-ribofuranuronamide
  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