6-(Chloromethyl)-2-(1-β-D-ribofuranosyl-5-amino-4-imidazolyl)-4H-4-oxopyrimidine | 138694-67-4

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 咪唑核糖核苷和核糖核苷酸
• 英文名称: 6-(Chloromethyl)-2-(1-β-D-ribofuranosyl-5-amino-4-imidazolyl)-4H-4-oxopyrimidine
• 英文别名: 2-[5-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]imidazol-4-yl]-6-(chloromethyl)-1H-pyrimidin-4-one；2-[5-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]imidazol-4-yl]-4-(chloromethyl)-1H-pyrimidin-6-one
• CAS: 138694-67-4
• 化学式: C₁₃H₁₆ClN₅O₅
• 分子量: 357.754
• InChiKey: OSZKVJHNMHQQAT-ZRFIDHNTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.2
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  155
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  3-β-D-Ribofuranosyl-7H-7-oxo-9-(chloromethyl)pyrimido<1,2-i>purine 在 ammonium hydroxide 作用下， 以 甲醇 为溶剂， 以71%的产率得到6-(Chloromethyl)-2-(1-β-D-ribofuranosyl-5-amino-4-imidazolyl)-4H-4-oxopyrimidine
  参考文献：
  名称：

  Reaction of nucleic acid bases with .alpha.-acetylenic esters. 5. Synthesis and properties of adenosine and cytidine derivatives

  摘要：

  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.

  DOI：

  10.1021/jo00031a045

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.