Acetic acid (2R,3R,4R,5R)-4-acetoxy-5-acetoxymethyl-2-{6-chloro-2-[(E)-(3-phenyl-acryloyl)amino]-purin-9-yl}-tetrahydro-furan-3-yl ester | 686768-03-6

• 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: Acetic acid (2R,3R,4R,5R)-4-acetoxy-5-acetoxymethyl-2-{6-chloro-2-[(E)-(3-phenyl-acryloyl)amino]-purin-9-yl}-tetrahydro-furan-3-yl ester
• CAS: 686768-03-6
• 化学式: C₂₅H₂₄ClN₅O₈
• 分子量: 557.947
• InChiKey: DXUVSNKXOSFXGN-FGSUIDRYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.46
• 重原子数：
  39.0
• 可旋转键数：
  8.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  160.83
• 氢给体数：
  1.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  Acetic acid (2R,3R,4R,5R)-4-acetoxy-5-acetoxymethyl-2-{6-chloro-2-[(E)-(3-phenyl-acryloyl)amino]-purin-9-yl}-tetrahydro-furan-3-yl ester 在 氨 作用下， 以 乙醇 为溶剂， 生成 2-[(3-Phenylacryloyl)amino]adenosine
  参考文献：
  名称：

  2-(N-Acyl) and 2-N-acyl-N6-substituted analogues of adenosine and their affinity at the human adenosine receptors

  摘要：

  A series of 2-(N-acyl) and 2-(N-acyl)-N-6-alkyladenosine analogues have been synthesized from the intermediate 2-amino-6-chloroadenosine derivatives (2b and 7) and evaluated for their affinity at the human A(1), A(2A), and A(3) receptors. We found that 2-(N-acyl) derivatives of adenosine showed relatively low affinity at A(2A) and A(3) receptors, while the N-6-cyclopentyl substituent in 4h and 4i induced high potency [A(1) (K-i) = 20.7 and 31.8 nM respectively] at the A(1) receptor and resulted therefore in increased selectivity for this subtype. The general synthetic methods and their binding studies are presented herein. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.01.011
• 作为产物：
  描述：

  2',3',5'-三乙酰鸟苷 在 吡啶 、 4-二甲氨基吡啶 、 四乙基氯化铵 、 N,N-二甲基苯胺 、 三氯氧磷 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 0.17h， 生成 Acetic acid (2R,3R,4R,5R)-4-acetoxy-5-acetoxymethyl-2-{6-chloro-2-[(E)-(3-phenyl-acryloyl)amino]-purin-9-yl}-tetrahydro-furan-3-yl ester
  参考文献：
  名称：

  2-(N-Acyl) and 2-N-acyl-N6-substituted analogues of adenosine and their affinity at the human adenosine receptors

  摘要：

  A series of 2-(N-acyl) and 2-(N-acyl)-N-6-alkyladenosine analogues have been synthesized from the intermediate 2-amino-6-chloroadenosine derivatives (2b and 7) and evaluated for their affinity at the human A(1), A(2A), and A(3) receptors. We found that 2-(N-acyl) derivatives of adenosine showed relatively low affinity at A(2A) and A(3) receptors, while the N-6-cyclopentyl substituent in 4h and 4i induced high potency [A(1) (K-i) = 20.7 and 31.8 nM respectively] at the A(1) receptor and resulted therefore in increased selectivity for this subtype. The general synthetic methods and their binding studies are presented herein. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.01.011