9-[2-O-acetyl-3-C-azido-3-deoxy-5-(methylcarbamoyl)-β-D-ribofuranosyl]-2,6-dichloropurine | 786665-97-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 9-[2-O-acetyl-3-C-azido-3-deoxy-5-(methylcarbamoyl)-β-D-ribofuranosyl]-2,6-dichloropurine
• CAS: 786665-97-2
• 化学式: C₁₃H₁₂Cl₂N₈O₄
• 分子量: 415.195
• InChiKey: MKYGBDQMUNGCEG-ADVRJHOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.39
• 重原子数：
  27.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  156.99
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  9-[2-O-acetyl-3-C-azido-3-deoxy-5-(methylcarbamoyl)-β-D-ribofuranosyl]-2,6-dichloropurine 在 吡啶 、 氨 、 三乙胺 、 三苯基膦 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 25.5h， 生成
  参考文献：
  名称：

  Exploring human adenosine A3 receptor complementarity and activity for adenosine analogues modified in the ribose and purine moiety

  摘要：

  In this paper we investigated the influence on affinity, selectivity and intrinsic activity upon modification of the adenosine agonist scaffold at the 3- and 5'-positions of the ribofuranosyl moiety and the 2- and N-6-positions of the purine base. This resulted in the synthesis of various analogues, that is, 3-12 and 24-33, with good hA(3)AR selectivity and moderate-to-high affinities (as in 32, K-i = 27 nM). Interesting was the ability to tune the intrinsic activity depending on the substituent introduced at the 3'-position. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.11.044
• 作为产物：
  描述：

  1,2:5,6-di-O-isopropylidene-3-O-triflyl-α-D-glucofuranose 在 吡啶 、 ruthenium trichloride 、 sodium periodate 、 甲酸 、 sodium azide 、 草酰氯 、 三氟甲磺酸三甲基硅酯 、 溶剂黄146 、 N,N-二甲基甲酰胺 作用下， 以 四氯化碳 、 二氯甲烷 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 92.0h， 生成 9-[2-O-acetyl-3-C-azido-3-deoxy-5-(methylcarbamoyl)-β-D-ribofuranosyl]-2,6-dichloropurine
  参考文献：
  名称：

  Design and synthesis of 3′-ureidoadenosine-5′-uronamides: effects of the 3′-ureido group on binding to the A3 adenosine receptor

  摘要：

  On the basis of high binding affinity at the A(3) adenosine receptor of 3'-aminoadenosine derivatives with hydrogen bonding donor ability, novel 3'-ureidoadenosine analogues were synthesized from 1,2:5,6-di-O-isopropylidene-D-glucose in order to lead to stronger hydrogen bonding than the corresponding 3'-aminoadeno sine derivatives. However, the synthesized 3'-ureidoadenosine analogues were totally devoid of binding affinity, because 3'-urea moiety caused steric and electrostatic repulsions at the binding site of the A(3) adenosine receptor, leading to conformational distortion. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.07.042