2-amino-5-aminomethyl-3,4-dihydro-7-β-D-ribofuranosyl-7H-pyrrolo<2,3-d>pyrimidin-4-one | 66048-70-2

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 吡咯并嘧啶核苷和核苷酸
• 英文名称: 2-amino-5-aminomethyl-3,4-dihydro-7-β-D-ribofuranosyl-7H-pyrrolo<2,3-d>pyrimidin-4-one
• 英文别名: 2-amino-5-aminomethyl-7-(β-D-ribofuranosyl)pyrrolo<2,3-d>pyrimidin-4-one；2-amino-5-aminomethyl-3,4-dihydro-7-β-D-ribofuranosyl-7H-pyrrolo[2,3-d]pyrimidin-4-one；7-Aminomethyl-7-deazaguanosine；2-amino-5-(aminomethyl)-7-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-3H-pyrrolo[2,3-d]pyrimidin-4-one
• CAS: 66048-70-2
• 化学式: C₁₂H₁₇N₅O₅
• 分子量: 311.297
• InChiKey: SOEYIPCQNRSIAV-IOSLPCCCSA-N

物化性质

• 熔点：
  149-151 °C
• 密度：
  2.07±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -3.6
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  168
• 氢给体数：
  6
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  5-cyano-2,4-dichloro-7-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)pyrrolo<2,3-d>pyrimidine 在 palladium on activated charcoal 二环己烷并-18-冠醚-6 、 氨 、 氢气 、 sodium nitrite 作用下， 以 盐酸 、 乙醇 、 水 为溶剂， 反应 134.0h， 生成 2-amino-5-aminomethyl-3,4-dihydro-7-β-D-ribofuranosyl-7H-pyrrolo<2,3-d>pyrimidin-4-one
  参考文献：
  名称：

  Synthesis of Pyrrolo[2,3-d]pyrimidines that are Structurally Related to Methylated Guanosines from tRNA and the Nucleoside Q Analogs, PreQ₀and PreQ₁

  摘要：

  The N-3- and N-2-methylated analogs of several 5-substituted 2-amino-7-(beta-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidin-4-ones were synthesized from 5-cyano-2,4-dichloro-7-(2,3,5-tri-(O>$) over bar under bar>-acetyl-beta-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidine (10) These compounds are analogs of nucleoside Q that are methylated in a manner similar to some of the naturally occurring methylated guanosines.

  DOI：

  10.1080/07328319708001355

文献信息

• Syntheses of hypermodified nucleoside q, and its biosynthetic precursors preq0 and preq1
  作者：Tadao Kondo、Kaoru Okamoto、Tadaaki Ohgi、Toshio Goto

  DOI：10.1016/s0040-4020(01)87419-6

  日期：——
• Synthesis of Pyrrolo[2,3-<i>d</i>]pyrimidines that are Structurally Related to Methylated Guanosines from tRNA and the Nucleoside Q Analogs, PreQ₀and PreQ₁
  作者：Chin Shu Cheng、Geoffrey C. Hoops、Robert A. Earl、Leroy B. Townsend

  DOI：10.1080/07328319708001355

  日期：1997.4

  The N-3- and N-2-methylated analogs of several 5-substituted 2-amino-7-(beta-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidin-4-ones were synthesized from 5-cyano-2,4-dichloro-7-(2,3,5-tri-(O>$) over bar under bar>-acetyl-beta-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidine (10) These compounds are analogs of nucleoside Q that are methylated in a manner similar to some of the naturally occurring methylated guanosines.