3-β-D-Ribofuranosyl-9H-9-oxo-7-(methoxycarbonyl)pyrimido<1,2-i>purine | 138694-64-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-β-D-Ribofuranosyl-9H-9-oxo-7-(methoxycarbonyl)pyrimido<1,2-i>purine
• 英文别名: 3-β-D-ribofuranosyl-9H-9-oxo-7-methoxycarbonylpyrimido<2,1-i>purine；3-β-D-Ribofuranosyl-9H-9-oxo-7-(methoxycarbonyl)pyrimido[1,2-i]purine；methyl 3-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-9-oxopyrimido[2,1-f]purine-7-carboxylate
• CAS: 138694-64-1
• 化学式: C₁₅H₁₅N₅O₇
• 分子量: 377.313
• InChiKey: GKSPIWOSDXTGQJ-FRJWGUMJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.2
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  159
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  3-β-D-Ribofuranosyl-9H-9-oxo-7-(methoxycarbonyl)pyrimido<1,2-i>purine 在 吡啶 、 氨 作用下， 反应 20.0h， 生成 6-amido-2-(1-β-D-ribofuranosyl-5-amino-4-imidazolyl)-4H-4-oxopyrimidine
  参考文献：
  名称：

  Boer, Richard F. de; Petra, Danielle G. I.; Wanner, Martin J., Heterocycles, 1995, vol. 41, # 6, p. 1197 - 1206

  摘要：

  DOI：
• 作为产物：
  描述：

  丁炔二酸二甲酯 、 腺苷 以78%的产率得到3-β-D-Ribofuranosyl-9H-9-oxo-7-(methoxycarbonyl)pyrimido<1,2-i>purine
  参考文献：
  名称：

  Synthesis of Fluorescent Adenosine Analogues1

  摘要：

  In the synthesis of a transition state inhibitor of the enzyme adenylosuccinate lyase two different [2,1-i]-pyrimido-purine derivatives are formed, of which one might be very interesting for cell biological research, due to its strong fluorescent properties.

  DOI：

  10.1080/15257779508012379

文献信息

• Reaction of nucleic acid bases with .alpha.-acetylenic esters. 5. Synthesis and properties of adenosine and cytidine derivatives
  作者：Pierre Roques、Jean Yves Le Gall、Liliane Lacombe、Martin Olomucki

  DOI：10.1021/jo00031a045

  日期：1992.2

  Alpha-Acetylenic esters are able to react under mild experimental conditions with the base moiety of adenosine and cytidine, while guanosine is unreactive. A double reaction of the triple bond and the ester group of the reagent with the NH2 group and the adjacent ring nitrogen of the base yields derivatives in which an additional pyrimidone ring is fused to the original base. These derivatives can exist in two isomeric forms. In alkaline solution, or by prolonged heating in water, the medium pyrimidine ring of adenosine derivatives opens by loss of carbon 5. If the derivatization is performed with chlorotetrolic (4-chloro-2-butynoic) acid esters, the modified nucleobases contain a chloromethyl side chain. Tests of the alkylating abilities of the latter in the two isomeric adenosine derivatives show that the chlorine can be easily substituted by a thiol in the presence of alkali; a partial Dimroth rearrangement of one of the reaction products is observed. The reaction with amines is accompanied by ring opening. Nucleic acids containing these alkylating base derivatives can be cross-linked to other macromolecules such as solid supports or contact proteins.