5-[β-D-glyceropentofuran-3'-ulos-1'-yl]-2-aminoquinazoline | 503321-54-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 5-[β-D-glyceropentofuran-3'-ulos-1'-yl]-2-aminoquinazoline
• 英文别名: (2R,5R)-5-(2-aminoquinazolin-5-yl)-2-(hydroxymethyl)oxolan-3-one
• CAS: 503321-54-8
• 化学式: C₁₃H₁₃N₃O₃
• 分子量: 259.265
• InChiKey: HQRUXIRBBYQORZ-VXGBXAGGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  98.3
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-[β-D-glyceropentofuran-3'-ulos-1'-yl]-2-aminoquinazoline 在 吡啶 、 三甲基氯硅烷 、 三乙酰氧基硼氢化钠 、 溶剂黄146 作用下， 以 乙腈 为溶剂， 反应 3.5h， 生成 N2-isobutyryl-5-[2'-deoxy-β-D-threo-pentofuranosyl]-2-aminoquinazoline
  参考文献：
  名称：

  Design of Triple Helix Forming C-Glycoside Molecules

  摘要：

  The modeling, synthesis, and characterization of oligomers containing 2-aminoquinazolin-5-yl 2'-deoxynucleotide residues are reported. The 2-arninoquinazoline residues sequence specifically bind via Hoogsteen base pairing as a third strand in the center of the major groove at TA base pair Watson-Crick duplex sequences. Evidence for the formation of a sequence specific three-stranded structure is based on thermal denaturation UV-vis and fluorescence studies. The novel 2-aminoquinazoline C-nucleoticle is a component of a system designed to overcome the homopurine requirement for triple helix structures.

  DOI：

  10.1021/ja028033x
• 作为产物：
  描述：

  2-溴-6-硝基苄溴 在 盐酸 、 palladium bis(dibenzylideneacetone)palladium⁽⁰⁾ 、 三叔丁基膦 、 硫酸 、 四丁基氟化铵 、 铁粉 、 溶剂黄146 、 三乙胺 作用下， 以 四氢呋喃 、 乙二醇乙醚 、 乙醇 为溶剂， 反应 3.51h， 生成 5-[β-D-glyceropentofuran-3'-ulos-1'-yl]-2-aminoquinazoline
  参考文献：
  名称：

  Design of Triple Helix Forming C-Glycoside Molecules

  摘要：

  The modeling, synthesis, and characterization of oligomers containing 2-aminoquinazolin-5-yl 2'-deoxynucleotide residues are reported. The 2-arninoquinazoline residues sequence specifically bind via Hoogsteen base pairing as a third strand in the center of the major groove at TA base pair Watson-Crick duplex sequences. Evidence for the formation of a sequence specific three-stranded structure is based on thermal denaturation UV-vis and fluorescence studies. The novel 2-aminoquinazoline C-nucleoticle is a component of a system designed to overcome the homopurine requirement for triple helix structures.

  DOI：

  10.1021/ja028033x

文献信息

• Design of Triple Helix Forming C-Glycoside Molecules
  作者：Jian-Sen Li、Yun-Hua Fan、Yi Zhang、Luis A. Marky、Barry Gold

  DOI：10.1021/ja028033x

  日期：2003.2.1

  The modeling, synthesis, and characterization of oligomers containing 2-aminoquinazolin-5-yl 2'-deoxynucleotide residues are reported. The 2-arninoquinazoline residues sequence specifically bind via Hoogsteen base pairing as a third strand in the center of the major groove at TA base pair Watson-Crick duplex sequences. Evidence for the formation of a sequence specific three-stranded structure is based on thermal denaturation UV-vis and fluorescence studies. The novel 2-aminoquinazoline C-nucleoticle is a component of a system designed to overcome the homopurine requirement for triple helix structures.