2-Chloro-3'-deoxy-3'-fluoro-N-[(3-iodophenyl)methyl]adenosine | 551929-69-2

• 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: 2-Chloro-3'-deoxy-3'-fluoro-N-[(3-iodophenyl)methyl]adenosine
• 英文别名: (2R,3S,4S,5R)-2-[2-chloro-6-[(3-iodophenyl)methylamino]purin-9-yl]-4-fluoro-5-(hydroxymethyl)oxolan-3-ol
• CAS: 551929-69-2
• 化学式: C₁₇H₁₆ClFIN₅O₃
• 分子量: 519.702
• InChiKey: BFUXSXWTXVGUOA-QQHRNGFRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 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：

  Toluene-4-sulfonic acid (2R,3R,4R,5R)-5-(tert-butyl-dimethyl-silanyloxymethyl)-4-fluoro-2-methoxy-tetrahydro-furan-3-yl ester 在 18-冠醚-6 、 三氟甲磺酸三甲基硅酯 、 硫酸 、 sodium methylate 、 溶剂黄146 作用下， 以 甲醇 、 乙醇 、 二甲基亚砜 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

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.
• Design and Synthesis of A₃Adenosine Receptor Ligands, 3′-Fluoro Analogues of Cl-IB-MECA
  作者：Hea Ok Kim、Moo Hong Lim、Jae Gyu Park、Hyung Ryong Moon、Kenneth A. Jacobson、Hee-Doo Kim、Moon Woo Chun、Lak Shin Jeong

  DOI：10.1081/ncn-120022701

  日期：2003.10

  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.