2-ethylthio-9-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)adenine | 173987-25-2

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: 2-ethylthio-9-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)adenine
• 英文别名: [(2R,3R,4R,5R)-5-(6-amino-2-ethylsulfanylpurin-9-yl)-3,4-dibenzoyloxyoxolan-2-yl]methyl benzoate
• CAS: 173987-25-2
• 化学式: C₃₃H₂₉N₅O₇S
• 分子量: 639.689
• InChiKey: SNIHSIYQYRZGCG-CTDWIVFPSA-N

物化性质

• 沸点：
  848.0±75.0 °C(Predicted)
• 密度：
  1.43±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  46
• 可旋转键数：
  13
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  183
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  2-ethylthio-9-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)adenine 在 吡啶 、 甲醇 、 potassium permanganate 、 氨 作用下， 以 甲醇 、 溶剂黄146 为溶剂， 反应 49.0h， 生成 海绵核苷
  参考文献：
  名称：

  A Simple Method for Synthesis of Spongosine, Azaspongosine, and Their Antiplatelet Effects

  摘要：

  Reaction of 2-ethylthioadenine (1) with protected ribose (2) in the presence of stannic chloride gave 2-ethylthioadenosine (4). Oxidation of 5 with potassium permanganate yielded the corresponding sulfone (6) which furnished spongosine (2) after treatment with sodium methoxide. Similarly, reactions of 7-amino-5-ethylthio-1,2,3-triazolo[4,5-d]pyrimidine (8) with the ribose (2) gave 8-azaspongosine (13). The compounds (4) and 2 demonstrated potent antiaggregatory effects both in human platelet-rich plasma and whole blood, whereas, the aza analog (13) showed no inhibitory activity on platelet aggregation. Both (4) and (7) inhibit platelet aggregation in the presence of adenosine deaminase, whereas, adenosine is non-inhibitory, suggesting that analogs (4) and (7) are poor substrates for adenosine deaminase.

  DOI：

  10.1080/15257779508010711
• 作为产物：
  描述：

  1-乙酰基-三-苄氧基-罗伯糖 、 2-(乙硫基)-9H-嘌呤-6-胺 以 硝基甲烷 为溶剂， 反应 18.0h， 以62.5%的产率得到2-ethylthio-9-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)adenine
  参考文献：
  名称：

  A Simple Method for Synthesis of Spongosine, Azaspongosine, and Their Antiplatelet Effects

  摘要：

  Reaction of 2-ethylthioadenine (1) with protected ribose (2) in the presence of stannic chloride gave 2-ethylthioadenosine (4). Oxidation of 5 with potassium permanganate yielded the corresponding sulfone (6) which furnished spongosine (2) after treatment with sodium methoxide. Similarly, reactions of 7-amino-5-ethylthio-1,2,3-triazolo[4,5-d]pyrimidine (8) with the ribose (2) gave 8-azaspongosine (13). The compounds (4) and 2 demonstrated potent antiaggregatory effects both in human platelet-rich plasma and whole blood, whereas, the aza analog (13) showed no inhibitory activity on platelet aggregation. Both (4) and (7) inhibit platelet aggregation in the presence of adenosine deaminase, whereas, adenosine is non-inhibitory, suggesting that analogs (4) and (7) are poor substrates for adenosine deaminase.

  DOI：

  10.1080/15257779508010711

文献信息

• A Simple Method for Synthesis of Spongosine, Azaspongosine, and Their Antiplatelet Effects
  作者：Lalit M. Ojha、Deepa Gulati、Neena Seth、Diwan S. Bhakuni、Ram Pratap、Kailash C. Agarwal

  DOI：10.1080/15257779508010711

  日期：1995.11

  Reaction of 2-ethylthioadenine (1) with protected ribose (2) in the presence of stannic chloride gave 2-ethylthioadenosine (4). Oxidation of 5 with potassium permanganate yielded the corresponding sulfone (6) which furnished spongosine (2) after treatment with sodium methoxide. Similarly, reactions of 7-amino-5-ethylthio-1,2,3-triazolo[4,5-d]pyrimidine (8) with the ribose (2) gave 8-azaspongosine (13). The compounds (4) and 2 demonstrated potent antiaggregatory effects both in human platelet-rich plasma and whole blood, whereas, the aza analog (13) showed no inhibitory activity on platelet aggregation. Both (4) and (7) inhibit platelet aggregation in the presence of adenosine deaminase, whereas, adenosine is non-inhibitory, suggesting that analogs (4) and (7) are poor substrates for adenosine deaminase.