3-((2R,3R,4S,5R)-3,4-Dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-6,7-dimethyl-3,5-dihydro-imidazo[1,2-a]purin-9-one | 577773-09-2

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 核苷和核苷酸类似物
• 英文名称: 3-((2R,3R,4S,5R)-3,4-Dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-6,7-dimethyl-3,5-dihydro-imidazo[1,2-a]purin-9-one
• 英文别名: Isowyosine；3-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6,7-dimethyl-5H-imidazo[1,2-a]purin-9-one
• CAS: 577773-09-2
• 化学式: C₁₄H₁₇N₅O₅
• 分子量: 335.319
• InChiKey: BINGDNLMMYSZFR-QYVSTXNMSA-N

物化性质

• 熔点：
  >150°C (dec.)
• 沸点：
  866.6±75.0 °C(Predicted)
• 密度：
  1.93±0.1 g/cm3(Predicted)
• 溶解度：
  DMSO（轻微、加热）、甲醇（非常轻微、加热）

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  132
• 氢给体数：
  4
• 氢受体数：
  7

制备方法与用途

7-甲基鸟苷是一种嘌呤核苷类似物，而嘌呤核苷类似物具有广泛抗肿瘤活性，特别是针对惰性淋巴系统恶性肿瘤。其抗癌机制主要依赖于抑制DNA合成和诱导细胞凋亡等过程。

反应信息

• 作为反应物：
  描述：

  3-((2R,3R,4S,5R)-3,4-Dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-6,7-dimethyl-3,5-dihydro-imidazo[1,2-a]purin-9-one 生成 Acetic acid (2R,3R,4R,5R)-4-acetoxy-5-acetoxymethyl-2-(6,7-dimethyl-9-oxo-5,9-dihydro-imidazo[1,2-a]purin-3-yl)-tetrahydro-furan-3-yl ester
  参考文献：
  名称：

  An efficient synthesis of y-nucleoside (wyosine) by regiospecific methylation of n4-desmethylwyosine using organozinc reagent

  摘要：

  DOI：

  10.1016/s0040-4039(00)95491-1
• 作为产物：
  描述：

  鸟苷 、 3-溴-2-丁酮 在 sodium hydride 作用下， 以 二甲基亚砜 为溶剂， 反应 2.0h， 以38 mg的产率得到3-((2R,3R,4S,5R)-3,4-Dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-6,7-dimethyl-3,5-dihydro-imidazo[1,2-a]purin-9-one
  参考文献：
  名称：

  Structures of two new “minimalist” modified nucleosides from archaeal tRNA

  摘要：

  The wyeosine (or wye) family of tricyclic ribonucleosides from archaeal and eukaryal tRNA(Phe) constitutes one of the most complex and interesting series of posttranscriptional RNA modifications, and has been the object of numerous studies of their chemical and biological synthesis and distribution. We report the structures of two minimally elaborated wye derivatives from archaea, raising the known number of wye nucleosides to eight: 3,4-dihydro-6-methyl-3-beta-D-ribofuranosyl-9H-imidazo[1,2-a]purine-9-one (symbol imG-14), and 3,4-dihydro-6,7-dimethyl-3-p-D-ribofuranosyl-9H-imidazo[1,2-a]purine-9-one (symbol imG2). Structures were determined primarily by mass spectrometry, and confirmed by comparison of physicochemical properties with those of chemically synthesized nucleosides. The nucleosides contain no amino acid side chains at C-7 (1H-imidazo[1,2-a]purine nomenclature) and are the only wye derivatives not methylated at N-4. These features suggest a minimal role for wye methyl groups and side chains in maintenance of anticodon stem-loop structures, and support the concept that archaeal tRNA nucleoside modification motifs are generally simpler than those of their counterparts in eukarya and bacteria. (C) 2003 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bioorg.2003.09.005

文献信息

• Structures of two new “minimalist” modified nucleosides from archaeal tRNA
  作者：Shaolian Zhou、Devarasetty Sitaramaiah、Kathleen R Noon、Rebecca Guymon、Takeshi Hashizume、James A McCloskey

  DOI：10.1016/j.bioorg.2003.09.005

  日期：2004.4

  The wyeosine (or wye) family of tricyclic ribonucleosides from archaeal and eukaryal tRNA(Phe) constitutes one of the most complex and interesting series of posttranscriptional RNA modifications, and has been the object of numerous studies of their chemical and biological synthesis and distribution. We report the structures of two minimally elaborated wye derivatives from archaea, raising the known number of wye nucleosides to eight: 3,4-dihydro-6-methyl-3-beta-D-ribofuranosyl-9H-imidazo[1,2-a]purine-9-one (symbol imG-14), and 3,4-dihydro-6,7-dimethyl-3-p-D-ribofuranosyl-9H-imidazo[1,2-a]purine-9-one (symbol imG2). Structures were determined primarily by mass spectrometry, and confirmed by comparison of physicochemical properties with those of chemically synthesized nucleosides. The nucleosides contain no amino acid side chains at C-7 (1H-imidazo[1,2-a]purine nomenclature) and are the only wye derivatives not methylated at N-4. These features suggest a minimal role for wye methyl groups and side chains in maintenance of anticodon stem-loop structures, and support the concept that archaeal tRNA nucleoside modification motifs are generally simpler than those of their counterparts in eukarya and bacteria. (C) 2003 Elsevier Inc. All rights reserved.
• An efficient synthesis of y-nucleoside (wyosine) by regiospecific methylation of n4-desmethylwyosine using organozinc reagent
  作者：H Bazin、X-X Zhou、C Glemarec、J Chattopadhyaya

  DOI：10.1016/s0040-4039(00)95491-1

  日期：1987.1