2-chloro-N⁶-(2-methylbenzyl)-9-(3-C-(methylcarbamoyl)-3-deoxy-β-D-ribofuranosyl)adenine | 1108175-17-2

• 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-N⁶-(2-methylbenzyl)-9-(3-C-(methylcarbamoyl)-3-deoxy-β-D-ribofuranosyl)adenine
• 英文别名: (2S,3S,4R,5R)-5-[2-chloro-6-[(2-methylphenyl)methylamino]purin-9-yl]-4-hydroxy-2-(hydroxymethyl)-N-methyloxolane-3-carboxamide
• CAS: 1108175-17-2
• 化学式: C₂₀H₂₃ClN₆O₄
• 分子量: 446.893
• InChiKey: JAQDVCVCUMSQET-DZDCQFRTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  134
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  methyl (2S,3R,4R,5R)-4-(benzoyloxy)-2-((benzoyloxy)methyl)-5-(2-chloro-6-((2-methylbenzyl)amino)-9H-purin-9-yl)tetrahydrofuran-3-carboxylate 、 甲胺 以 四氢呋喃 、 水 为溶剂， 反应 1.0h， 以25%的产率得到2-chloro-N⁶-(2-methylbenzyl)-9-(3-C-(methylcarbamoyl)-3-deoxy-β-D-ribofuranosyl)adenine
  参考文献：
  名称：

  Synthesis of 3′-Acetamidoadenosine Derivatives as Potential A₃Adenosine Receptor Agonists

  摘要：

  On the basis of high binding affinity of 3'-aminoadenosine derivatives 2b at the human A(3) adenosine receptor (AR), 3'-acetamidoadenosine derivatives 3a-e were synthesized from 1,2:5,6-di-O-isopropylidene-D-glucose via stereoselective hydroboration as a key step. Although all synthesized compounds were totally devoid of binding affinity at the human A(3)AR, our results revealed that 3'-position of adenosine can only be tolerated with small size of a hydrogen bonding donor like hydroxyl or amino group in the binding site of human A(3)AR.

  DOI：

  10.1080/15257770801944436

文献信息

• Synthesis of 3′-Acetamidoadenosine Derivatives as Potential A₃Adenosine Receptor Agonists
  作者：Moon Woo Chun、Sung Wook Choi、Tae Kyung Kang、Won Jun Choi、Hea Ok Kim、Zhan-Guo Gao、Kenneth A. Jacobson、Lak Shin Jeong

  DOI：10.1080/15257770801944436

  日期：2008.4.4

  On the basis of high binding affinity of 3'-aminoadenosine derivatives 2b at the human A(3) adenosine receptor (AR), 3'-acetamidoadenosine derivatives 3a-e were synthesized from 1,2:5,6-di-O-isopropylidene-D-glucose via stereoselective hydroboration as a key step. Although all synthesized compounds were totally devoid of binding affinity at the human A(3)AR, our results revealed that 3'-position of adenosine can only be tolerated with small size of a hydrogen bonding donor like hydroxyl or amino group in the binding site of human A(3)AR.