1-deoxy-1-(6-iodo-9H-purin-9-yl)-2,3-O-isopropylidene-N-ethyl-β-D-ribofuranuronamide | 924281-79-8

• 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-iodo-9H-purin-9-yl)-2,3-O-isopropylidene-N-ethyl-β-D-ribofuranuronamide
• 英文别名: (3aS,4S,6R,6aR)-6-(6-iodo-9H-purin-9-yl)-2,2-dimethyl-tetrahydrofuro[3,4-d][1,3]dioxole-4-carboxylic acid ethylamide；(3aR,4R,6S,6aS)-N-ethyl-4-(6-iodopurin-9-yl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxole-6-carboxamide
• CAS: 924281-79-8
• 化学式: C₁₅H₁₈IN₅O₄
• 分子量: 459.244
• InChiKey: LCVJVHNNQPVPAK-QOBXEIRBSA-N

物化性质

• 密度：
  2.02±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  100
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-deoxy-1-(6-iodo-9H-purin-9-yl)-2,3-O-isopropylidene-N-ethyl-β-D-ribofuranuronamide 在 水 、 三乙胺 、 三氟乙酸 作用下， 以 乙醇 为溶剂， 反应 3.0h， 生成 1-deoxy-1-{6-[N'-(furan-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 、 亚硝酸异戊酯 作用下， 反应 1.0h， 以60%的产率得到1-deoxy-1-(6-iodo-9H-purin-9-yl)-2,3-O-isopropylidene-N-ethyl-β-D-ribofuranuronamide
  参考文献：
  名称：

  ADENOSINE A2B RECEPTOR AGONISTS

  摘要：

  本发明提供了以下式子中R1、R2、R3和n的含义如规范所述的化合物，作为腺苷A2B受体激动剂，因此可用于治疗哺乳动物中由A2B受体介导的疾病，包括但不限于感染性休克、囊性纤维化、阳痿、腹泻和心脏疾病。心脏疾病包括由高血压、动脉硬化和心脏病发作引起的增生。

  公开号：

  US20070281902A1

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.