2-((4'R,6'R)-4'-(hydroxymethyl)tetrahydrospiro[cyclopentane-1,2'-furo[3,4-d][1,3]dioxol]-6'-yl)-1,2,4-triazine-3,5(2H,4H)-dione | 93475-80-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-((4'R,6'R)-4'-(hydroxymethyl)tetrahydrospiro[cyclopentane-1,2'-furo[3,4-d][1,3]dioxol]-6'-yl)-1,2,4-triazine-3,5(2H,4H)-dione
• 英文别名: 2-(O²,O³-cyclopentylidene-β-D-ribofuranosyl)-2H-[1,2,4]triazine-3,5-dione；2',3'-O-Cyclopentyliden-6-aza-uridin
• CAS: 93475-80-0
• 化学式: C₁₃H₁₇N₃O₆
• 分子量: 311.294
• InChiKey: PFXSATVYSQWSOE-QCNRFFRDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.12
• 重原子数：
  22.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  115.67
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为产物：
  描述：

  6-氮杂尿苷 、 环戊酮 在 盐酸 、 原甲酸三乙酯 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以33%的产率得到2-((4'R,6'R)-4'-(hydroxymethyl)tetrahydrospiro[cyclopentane-1,2'-furo[3,4-d][1,3]dioxol]-6'-yl)-1,2,4-triazine-3,5(2H,4H)-dione
  参考文献：
  名称：

  Identification of Nucleoside Analogs as Inducers of Neuronal Differentiation in a Human Reporter Cell Line and Adult Stem Cells

  摘要：

  Nucleoside analogs (NSAs) were among the first chemotherapeutic agents and could also be useful for the manipulation of cell fate. To investigate the potential of NSAs for the induction of neuronal differentiation, we developed a novel phenotypic assay based on a human neuron‐committed teratocarcinoma cell line (NT2) as a model for neuronal progenitors and constructed a NT2‐based reporter cell line that expressed eGFP under the control of a neuron‐specific promoter. We tested 38 structurally related NSAs and determined their activity to induce neuronal differentiation by immunocytochemistry of neuronal marker proteins, live cell imaging, fluorometric detection and immunoblot analysis. We identified twelve NSAs, which induced neuronal differentiation to different extents. NSAs with highest activity carried a halogen substituent at their pyrimidine nucleobase and an unmodified or 2′‐O‐methyl substituted 2‐deoxy‐β‐D‐ribofuranosyl residue as glyconic moiety. Cladribine, a purine nucleoside with similar structural features and in use to treat leukemia and multiple sclerosis, induced also differentiation of adult human neural crest‐derived stem cells. Our results suggest that NSAs could be useful for the manipulation of neuronal cell fate in cell replacement therapy or treatment of neurodegenerative disorders. The data on the structure and function relationship will help to design compounds with increased activity and low toxicity.

  DOI：

  10.1111/cbdd.12488