1-deoxy-1-{6-[N'-(5-methylthiophene-2-carbonyl)hydrazino]-9H-purin-9-yl}-2,3-O-isopropylidene-N-ethyl-β-D-ribofuranuronamide | 924281-88-9

• 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-[N'-(5-methylthiophene-2-carbonyl)hydrazino]-9H-purin-9-yl}-2,3-O-isopropylidene-N-ethyl-β-D-ribofuranuronamide
• 英文别名: (3aS,4S,6R,6aR)-2,2-dimethyl-6-{6-[N'-(5-methyl-thiophene-2-carbonyl)-hydrazino]-9H-purin-9-yl}-tetrahydrofuro[3,4-d][1,3]dioxole-4-carboxylic acid ethylamide；(3aR,4R,6S,6aS)-N-ethyl-2,2-dimethyl-4-[6-[2-(5-methylthiophene-2-carbonyl)hydrazinyl]purin-9-yl]-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxole-6-carboxamide
• CAS: 924281-88-9
• 化学式: C₂₁H₂₅N₇O₅S
• 分子量: 487.539
• InChiKey: NMIZNQDIIIMHDF-IGMJJTELSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  34
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  170
• 氢给体数：
  3
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  1-deoxy-1-{6-[N'-(5-methylthiophene-2-carbonyl)hydrazino]-9H-purin-9-yl}-2,3-O-isopropylidene-N-ethyl-β-D-ribofuranuronamide 在 水 、 三氟乙酸 作用下， 反应 3.0h， 以91%的产率得到1-deoxy-1-{6-[N'-(5-methylthiophene-2-carbonyl)hydrazino]-9H-purin-9-yl}-N-ethyl-β-D-ribofuranuronamide
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Novel 1-Deoxy-1-[6-[((hetero)arylcarbonyl)hydrazino]- 9H-purin-9-yl]-N-ethyl-β-d-ribofuranuronamide Derivatives as Useful Templates for the Development of A_2B Adenosine Receptor Agonists

  摘要：

  The lack of molecules endowed with selective and potent agonistic activity toward the hA(2B) adenosine receptors has limited the studies on this pharmacological target and consequently the evaluation of its therapeutic potential. We report the design and the synthesis of the first potent (EC50 in the nanomolar range) and selective hA(2B) adenosine receptor agonists consisting of 1-deoxy-1-[6-[((hetero)arylcarbonyl)hydrazino]-9H-purin-9-yl]-N-ethyl-beta-D-ribofuranuronamide derivatives. The concurrent effect of 6-substitution of the purine nucleus with a ((hetero)arylcarbonyl)hydrazino function and a 2-chloro substitution has been investigated in such NECA derivatives.

  DOI：

  10.1021/jm061170a
• 作为产物：
  描述：

  5'-乙基甲酰氨基-2',3'-异亚丙基腺苷 在 二碘甲烷 、 三乙胺 、 亚硝酸异戊酯 作用下， 以 乙醇 为溶剂， 反应 1.0h， 生成 1-deoxy-1-{6-[N'-(5-methylthiophene-2-carbonyl)hydrazino]-9H-purin-9-yl}-2,3-O-isopropylidene-N-ethyl-β-D-ribofuranuronamide
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Novel 1-Deoxy-1-[6-[((hetero)arylcarbonyl)hydrazino]- 9H-purin-9-yl]-N-ethyl-β-d-ribofuranuronamide Derivatives as Useful Templates for the Development of A_2B Adenosine Receptor Agonists

  摘要：

  The lack of molecules endowed with selective and potent agonistic activity toward the hA(2B) adenosine receptors has limited the studies on this pharmacological target and consequently the evaluation of its therapeutic potential. We report the design and the synthesis of the first potent (EC50 in the nanomolar range) and selective hA(2B) adenosine receptor agonists consisting of 1-deoxy-1-[6-[((hetero)arylcarbonyl)hydrazino]-9H-purin-9-yl]-N-ethyl-beta-D-ribofuranuronamide derivatives. The concurrent effect of 6-substitution of the purine nucleus with a ((hetero)arylcarbonyl)hydrazino function and a 2-chloro substitution has been investigated in such NECA derivatives.

  DOI：

  10.1021/jm061170a

文献信息

• Synthesis and Biological Evaluation of Novel 1-Deoxy-1-[6-[((hetero)arylcarbonyl)hydrazino]- 9<i>H</i>-purin-9-yl]-<i>N</i>-ethyl-β-<scp>d</scp>-ribofuranuronamide Derivatives as Useful Templates for the Development of A_2B Adenosine Receptor Agonists
  作者：Pier Giovanni Baraldi、Delia Preti、Mojgan Aghazadeh Tabrizi、Francesca Fruttarolo、Romeo Romagnoli、Maria Dora Carrion、Luisa Carlota Lopez Cara、Allan R. Moorman、Katia Varani、Pier Andrea Borea

  DOI：10.1021/jm061170a

  日期：2007.1.1

  The lack of molecules endowed with selective and potent agonistic activity toward the hA(2B) adenosine receptors has limited the studies on this pharmacological target and consequently the evaluation of its therapeutic potential. We report the design and the synthesis of the first potent (EC50 in the nanomolar range) and selective hA(2B) adenosine receptor agonists consisting of 1-deoxy-1-[6-[((hetero)arylcarbonyl)hydrazino]-9H-purin-9-yl]-N-ethyl-beta-D-ribofuranuronamide derivatives. The concurrent effect of 6-substitution of the purine nucleus with a ((hetero)arylcarbonyl)hydrazino function and a 2-chloro substitution has been investigated in such NECA derivatives.