(2R,3S,4S,5R)-2-(2-Chloro-6-(methylamino)-9H-purin-9-yl)-4-fluoro-5-(hydroxymethyl)tetrahydrofuran-3-ol | 122654-31-3

• 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: (2R,3S,4S,5R)-2-(2-Chloro-6-(methylamino)-9H-purin-9-yl)-4-fluoro-5-(hydroxymethyl)tetrahydrofuran-3-ol
• 英文别名: (2R,3S,4S,5R)-2-[2-chloro-6-(methylamino)purin-9-yl]-4-fluoro-5-(hydroxymethyl)oxolan-3-ol
• CAS: 122654-31-3
• 化学式: C₁₁H₁₃ClFN₅O₃
• 分子量: 317.707
• InChiKey: DUOQYMIAHQYRQT-QYYRPYCUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  105
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  methyl 5-O-benzoyl-3-deoxy-3-fluoro-β-D-ribofuranoside 在 吡啶 、 三氟甲磺酸三甲基硅酯 、 硫酸 、 sodium methylate 、 溶剂黄146 、 三乙胺 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 14.25h， 生成 (2R,3S,4S,5R)-2-(2-Chloro-6-(methylamino)-9H-purin-9-yl)-4-fluoro-5-(hydroxymethyl)tetrahydrofuran-3-ol
  参考文献：
  名称：

  Design, synthesis and binding affinity of 3′-fluoro analogues of Cl-IB-MECA as adenosine A3 receptor ligands

  摘要：

  Several 3'-fluoro analogues, la, 1b, and le of selective and potent adenosine A(3) receptor agonist, Cl-IB-MECA were synthesized from D-xylose via highly regioselective opening of lyxo-epoxides, 8a and 811 with fluoride anion. Compared to the high binding affinity of Cl-IB-MECA to the A(3) adenosine receptor, the corresponding 3-fluoro derivative showed remarkably decreased binding affinity, indicating that 3'-hydroxyl group acts as hydrogen bonding acceptor, not hydrogen bonding donor like fluorine atom in binding to the A(3) adenosine receptor. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00027-1

文献信息

• Design, synthesis and binding affinity of 3′-fluoro analogues of Cl-IB-MECA as adenosine A3 receptor ligands
  作者：Moo Hong Lim、Hea Ok Kim、Hyung Ryong Moon、Seung Jin Lee、Moon Woo Chun、Zhan-Guo Gao、Neli Melman、Kenneth A Jacobson、Joong Hyup Kim、Lak Shin Jeong

  DOI：10.1016/s0960-894x(03)00027-1

  日期：2003.3

  Several 3'-fluoro analogues, la, 1b, and le of selective and potent adenosine A(3) receptor agonist, Cl-IB-MECA were synthesized from D-xylose via highly regioselective opening of lyxo-epoxides, 8a and 811 with fluoride anion. Compared to the high binding affinity of Cl-IB-MECA to the A(3) adenosine receptor, the corresponding 3-fluoro derivative showed remarkably decreased binding affinity, indicating that 3'-hydroxyl group acts as hydrogen bonding acceptor, not hydrogen bonding donor like fluorine atom in binding to the A(3) adenosine receptor. (C) 2003 Elsevier Science Ltd. All rights reserved.