9-(3-amino-3-deoxy-β-D-ribofuranosyl)-2-iodo-N⁶-methyladenine | 879398-40-0

• 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: 9-(3-amino-3-deoxy-β-D-ribofuranosyl)-2-iodo-N⁶-methyladenine
• 英文别名: 3'-Amino-3'-deoxy-2-iodo-N-methyladenosine；(2R,3R,4S,5S)-4-amino-5-(hydroxymethyl)-2-[2-iodo-6-(methylamino)purin-9-yl]oxolan-3-ol
• CAS: 879398-40-0
• 化学式: C₁₁H₁₅IN₆O₃
• 分子量: 406.183
• InChiKey: QSMUJBJYEOFLSP-QYYRPYCUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 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：
  131
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  9-(3-amino-3-deoxy-β-D-ribofuranosyl)-2-iodo-N⁶-methyladenine 、 苯乙炔 在 bis-triphenylphosphine-palladium(II) chloride copper(l) iodide 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以81%的产率得到9-(3-amino-3-deoxy-β-D-ribofuranosyl)-N⁶-methyl-2-phenylethynyladenine
  参考文献：
  名称：

  Synthesis of hypermodified adenosine derivatives as selective adenosine A3 receptor ligands

  摘要：

  We investigated the A(3)AR affinity and selectivity of a series of 2-substituted 3'-azido and 3'-amino adenosine derivatives as well as some 5-uronamide derivatives thereof. All compounds showed high A3AR selectivity. While the 3'-azides appeared to be A3AR antagonists with moderate A3AR affinity, their 3'-amino congeners exhibit significantly improved A3AR affinity and behave as partial agonists. For both the 3'-azides and the 3'-amines, the 5'-methylcarbamoyl modification improved the overall affinity. Introduction of a 2-phenylethynyl substituent provided high affinity for the A3AR. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.09.062
• 作为产物：
  描述：

  2-氨基-6-氯嘌呤 在 copper(l) iodide N,O-双三甲硅基乙酰胺 、 二碘甲烷 、 三氟甲磺酸三甲基硅酯 、 氨 、 碘 、 sodium 、 三乙胺 、 三苯基膦 、 亚硝酸异戊酯 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 水 、 乙腈 为溶剂， 反应 54.75h， 生成 9-(3-amino-3-deoxy-β-D-ribofuranosyl)-2-iodo-N⁶-methyladenine
  参考文献：
  名称：

  Synthesis of hypermodified adenosine derivatives as selective adenosine A3 receptor ligands

  摘要：

  We investigated the A(3)AR affinity and selectivity of a series of 2-substituted 3'-azido and 3'-amino adenosine derivatives as well as some 5-uronamide derivatives thereof. All compounds showed high A3AR selectivity. While the 3'-azides appeared to be A3AR antagonists with moderate A3AR affinity, their 3'-amino congeners exhibit significantly improved A3AR affinity and behave as partial agonists. For both the 3'-azides and the 3'-amines, the 5'-methylcarbamoyl modification improved the overall affinity. Introduction of a 2-phenylethynyl substituent provided high affinity for the A3AR. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.09.062