2,6-dichloro-9-[(2,3-O-isopropylidene)-4-thio-β-D-ribofuranosyl]purine | 900810-22-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: 2,6-dichloro-9-[(2,3-O-isopropylidene)-4-thio-β-D-ribofuranosyl]purine
• CAS: 900810-22-2
• 化学式: C₁₃H₁₄Cl₂N₄O₃S
• 分子量: 377.251
• InChiKey: GOEGLXDBHPMWEK-IOSLPCCCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.26
• 重原子数：
  23.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  82.29
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  2,6-dichloro-9-[(2,3-O-isopropylidene)-4-thio-β-D-ribofuranosyl]purine 在 溶剂黄146 、 三乙胺 作用下， 以 乙醇 、 水 为溶剂， 反应 12.0h， 生成 2-chloro-6-(3-iodobenzyl)amino-9-(4-thio-β-D-ribofuranosyl)purine
  参考文献：
  名称：

  Design, synthesis, and biological activity of N6-substituted-4′-thioadenosines at the human A3 adenosine receptor

  摘要：

  A large series of N-6-substituted-4'-thioadenosines were synthesized starting from D-gulonic-gamma-Iactone, and structure-activity relationships were studied at the human A(3) and other subtypes of adenosine receptors (ARs). 2-Chloro-substituted and 2-H analogues were compared. 2-Chloro-N-6-methyl-4'-thioadeno sine 19b was a highly potent and selective agonist (K-i = 0.8 +/- 0.1 nM in binding) at the A(3)AR, and displayed the same relative efficacy in receptor activation as a known full agonist, Cl-IB-MECA. Most of N6-substituted-4'-thioadenosines were less potent in binding than the corresponding N-6-substituted-adenosines or N-6-substituted-4'thioadenosine-5'-uronamides. N-6-(3-lodobenzyl) derivative 19g was demonstrated to be an A(3)AR-selective partial agonist displaying a Ki value of 3.2 nM. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.03.030
• 作为产物：
  描述：

  benzoic acid (3aS,4R,6R,6aR)-6-(2,6-dichloro-purin-9-yl)-2,2-dimethyl-tetrahydro-thieno[3,4-d][1,3]dioxol-4-ylmethyl ester 在 甲基碘化镁 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 4.0h， 以65%的产率得到2,6-dichloro-9-[(2,3-O-isopropylidene)-4-thio-β-D-ribofuranosyl]purine
  参考文献：
  名称：

  Design, synthesis, and biological activity of N6-substituted-4′-thioadenosines at the human A3 adenosine receptor

  摘要：

  A large series of N-6-substituted-4'-thioadenosines were synthesized starting from D-gulonic-gamma-Iactone, and structure-activity relationships were studied at the human A(3) and other subtypes of adenosine receptors (ARs). 2-Chloro-substituted and 2-H analogues were compared. 2-Chloro-N-6-methyl-4'-thioadeno sine 19b was a highly potent and selective agonist (K-i = 0.8 +/- 0.1 nM in binding) at the A(3)AR, and displayed the same relative efficacy in receptor activation as a known full agonist, Cl-IB-MECA. Most of N6-substituted-4'-thioadenosines were less potent in binding than the corresponding N-6-substituted-adenosines or N-6-substituted-4'thioadenosine-5'-uronamides. N-6-(3-lodobenzyl) derivative 19g was demonstrated to be an A(3)AR-selective partial agonist displaying a Ki value of 3.2 nM. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.03.030