((2R,3R,4S,5R)-4-(benzoyloxy)-5-(2,6-dichloro-9H-purin-9-yl)-3-fluorotetrahydrofuran-2-yl)methyl benzoate | 122654-35-7

• 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,3R,4S,5R)-4-(benzoyloxy)-5-(2,6-dichloro-9H-purin-9-yl)-3-fluorotetrahydrofuran-2-yl)methyl benzoate
• CAS: 122654-35-7
• 化学式: C₂₄H₁₇Cl₂FN₄O₅
• 分子量: 531.327
• InChiKey: XUONTVAFVCJOBB-BZSOYRFXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.45
• 重原子数：
  36.0
• 可旋转键数：
  6.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  105.43
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  ((2R,3R,4S,5R)-4-(benzoyloxy)-5-(2,6-dichloro-9H-purin-9-yl)-3-fluorotetrahydrofuran-2-yl)methyl benzoate 在 sodium methylate 作用下， 以 甲醇 、 乙醇 为溶剂， 生成 2-Chloro-3'-deoxy-3'-fluoro-N-[(3-iodophenyl)methyl]adenosine
  参考文献：
  名称：

  Design and Synthesis of A₃Adenosine Receptor Ligands, 3′-Fluoro Analogues of Cl-IB-MECA

  摘要：

  Synthesis of 3'-deoxy-3'-fluoro-N-6-substituted adenosines as bioisosteres of Cl-IB-MECA and their binding affinities to A(3) adenosine receptor are described.

  DOI：

  10.1081/ncn-120022701
• 作为产物：
  描述：

  methyl-[O³,O⁵-isopropylidene-O²-(toluene-4-sulfonyl)-α-D-xylofuranoside] 在 吡啶 、 potassium hydrogen bifluoride 、 18-冠醚-6 、 三氟甲磺酸三甲基硅酯 、 硫酸 、 sodium methylate 、 sodium fluoride 、 溶剂黄146 作用下， 以 甲醇 、 乙二醇 、 二甲基亚砜 为溶剂， 生成 ((2R,3R,4S,5R)-4-(benzoyloxy)-5-(2,6-dichloro-9H-purin-9-yl)-3-fluorotetrahydrofuran-2-yl)methyl benzoate
  参考文献：
  名称：

  Design and Synthesis of A₃Adenosine Receptor Ligands, 3′-Fluoro Analogues of Cl-IB-MECA

  摘要：

  Synthesis of 3'-deoxy-3'-fluoro-N-6-substituted adenosines as bioisosteres of Cl-IB-MECA and their binding affinities to A(3) adenosine receptor are described.

  DOI：

  10.1081/ncn-120022701

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.