2',3'',4''-tri-O-acetyl-2'',5',6''-tri-O-benzyl-3'O-α-D-glucopyranosyl-2,6-dichloro-9-β-D-ribofuranosylpurine | 628316-75-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2',3'',4''-tri-O-acetyl-2'',5',6''-tri-O-benzyl-3'O-α-D-glucopyranosyl-2,6-dichloro-9-β-D-ribofuranosylpurine
• 英文别名: [(2R,3R,4S,5R,6R)-4-acetyloxy-6-[(2R,3R,4R,5R)-4-acetyloxy-5-(2,6-dichloropurin-9-yl)-2-(phenylmethoxymethyl)oxolan-3-yl]oxy-5-phenylmethoxy-2-(phenylmethoxymethyl)oxan-3-yl] acetate
• CAS: 628316-75-6
• 化学式: C₄₃H₄₄Cl₂N₄O₁₂
• 分子量: 879.748
• InChiKey: WLWVZJJPSISOML-URFGGMKHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  61
• 可旋转键数：
  20
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  178
• 氢给体数：
  0
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  2',3'',4''-tri-O-acetyl-2'',5',6''-tri-O-benzyl-3'O-α-D-glucopyranosyl-2,6-dichloro-9-β-D-ribofuranosylpurine 在 甲醇 、 sodium methylate 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 4.5h， 生成 2'',5',6''-tri-O-benzyl-3'O-α-D-glucopyranosyl-2-chloro-6-methylamino-9-β-D-ribofuranosylpurine
  参考文献：
  名称：

  Synthesis and Ca²⁺-Mobilizing Activity of Purine-Modified Mimics of Adenophostin A:  A Model for the Adenophostin−Ins(1,4,5)P₃ Receptor Interaction

  摘要：

  The synthesis of a series of adenophostin A analogues modified at C-6 and C-2 of adenine is described. The target compounds were synthesized by a convergent route involving a modified Vorbruggen condensation of either 6-chloropurine or 2,6-dichloropurine with a protected disaccharide, yielding two versatile intermediates capable of undergoing substitution with a range of nucleophiles. The new analogues showed a range of abilities to mobilize Ca2+ from the intracellular stores of permeabilized hepatocytes and are among the first totally synthetic compounds to approach the activity of adenophostin A. In agreement with the biological results, docking studies of adenophostin A using the recently reported X-ray crystal structure of the type 1 Ins(1,4,5)P-3 receptor binding core suggested that, in likely binding modes of adenophostin A, the area around N-6 may be relatively open, identifying this region of the adenophostin A molecule as a promising target for further elaboration. The docking results also point to specific interactions involving residues within the binding domain of the Ins(1,4,5)P-3 receptor that may be involved in the molecular recognition of the adenophostins.

  DOI：

  10.1021/jm030883f
• 作为产物：
  描述：

  2,6-二氯嘌呤 、 1,2,3',4'-Tetra-O-acetyl-2',5,6'-tri-O-benzyl-3-O-α-D-glucopyranosyl-D-ribofuranose 在 三氟甲磺酸三甲基硅酯 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以67%的产率得到2',3'',4''-tri-O-acetyl-2'',5',6''-tri-O-benzyl-3'O-α-D-glucopyranosyl-2,6-dichloro-9-β-D-ribofuranosylpurine
  参考文献：
  名称：

  Synthesis and Ca²⁺-Mobilizing Activity of Purine-Modified Mimics of Adenophostin A:  A Model for the Adenophostin−Ins(1,4,5)P₃ Receptor Interaction

  摘要：

  The synthesis of a series of adenophostin A analogues modified at C-6 and C-2 of adenine is described. The target compounds were synthesized by a convergent route involving a modified Vorbruggen condensation of either 6-chloropurine or 2,6-dichloropurine with a protected disaccharide, yielding two versatile intermediates capable of undergoing substitution with a range of nucleophiles. The new analogues showed a range of abilities to mobilize Ca2+ from the intracellular stores of permeabilized hepatocytes and are among the first totally synthetic compounds to approach the activity of adenophostin A. In agreement with the biological results, docking studies of adenophostin A using the recently reported X-ray crystal structure of the type 1 Ins(1,4,5)P-3 receptor binding core suggested that, in likely binding modes of adenophostin A, the area around N-6 may be relatively open, identifying this region of the adenophostin A molecule as a promising target for further elaboration. The docking results also point to specific interactions involving residues within the binding domain of the Ins(1,4,5)P-3 receptor that may be involved in the molecular recognition of the adenophostins.

  DOI：

  10.1021/jm030883f