3'-O-acetyl-N⁶-benzoyl-8-(1-N-acetylhistamino)-2'-deoxyadenosine | 151545-38-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: 3'-O-acetyl-N⁶-benzoyl-8-(1-N-acetylhistamino)-2'-deoxyadenosine
• 英文别名: [(2R,3S,5R)-5-[8-[2-(3-acetylimidazol-4-yl)ethylamino]-6-benzamidopurin-9-yl]-2-(hydroxymethyl)oxolan-3-yl] acetate
• CAS: 151545-38-9
• 化学式: C₂₆H₂₈N₈O₆
• 分子量: 548.558
• InChiKey: QJELQWIUIVIOTP-PWRODBHTSA-N

物化性质

• 密度：
  1.53±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  40
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  175
• 氢给体数：
  3
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  3'-O-acetyl-N⁶-benzoyl-8-(1-N-acetylhistamino)-2'-deoxyadenosine 在 吡啶 、 N-甲基咪唑 、 二氯乙酸 、 mesitylensulphonyl-3-nitrotriazole 、 氨 作用下， 以 甲醇 为溶剂， 反应 24.0h， 生成
  参考文献：
  名称：

  Synthesis and conformational studies of d(TpA) and r(UpA) conjugated with histamine and ethylenediamine

  摘要：

  Dinucleotides (Figure 1b-d) possessing histamino/ethylenediamino substituents at C8 of adenine have been synthesised for modelling the molecular interactions that occur at catalytic site of nucleases. These compounds have been designed for putative molecular recognition of internucleotide phosphate by a complementary group (imidazole/-NH2) in the pendant C-8 side chains. H-1 NMR spectroscopic analysis of synthesised model compounds indicate that C-8 modification leads to increase in percentage of S conformation of modified sugar while still maintaining an anti glycosyl torsion as in unmodified analog d(TpA). The C-8 side chain functionality (histamine/ethylenediamine) is probably involved in intramolecular interaction (electrostatic/ hydrogen bond) with the phosphate and/or 2'OH in (14). Such predisposition of side chain catalytic groups is important in developing appropriate models for active site of nucleases.

  DOI：

  10.1016/s0040-4020(01)89916-6
• 作为产物：
  描述：

  8-溴-2'-脱氧腺苷 在 吡啶 、 二氯乙酸 、 三甲基氯硅烷 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 24.08h， 生成 3'-O-acetyl-N⁶-benzoyl-8-(1-N-acetylhistamino)-2'-deoxyadenosine
  参考文献：
  名称：

  Synthesis and conformational studies of d(TpA) and r(UpA) conjugated with histamine and ethylenediamine

  摘要：

  Dinucleotides (Figure 1b-d) possessing histamino/ethylenediamino substituents at C8 of adenine have been synthesised for modelling the molecular interactions that occur at catalytic site of nucleases. These compounds have been designed for putative molecular recognition of internucleotide phosphate by a complementary group (imidazole/-NH2) in the pendant C-8 side chains. H-1 NMR spectroscopic analysis of synthesised model compounds indicate that C-8 modification leads to increase in percentage of S conformation of modified sugar while still maintaining an anti glycosyl torsion as in unmodified analog d(TpA). The C-8 side chain functionality (histamine/ethylenediamine) is probably involved in intramolecular interaction (electrostatic/ hydrogen bond) with the phosphate and/or 2'OH in (14). Such predisposition of side chain catalytic groups is important in developing appropriate models for active site of nucleases.

  DOI：

  10.1016/s0040-4020(01)89916-6