2-MeS-nebularine | 27640-80-8

• 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-MeS-nebularine
• 英文别名: (1R)-1-(2-methylsulfanyl-purin-9-yl)-D-1,4-anhydro-ribitol；(1R)-1-(2-Methylmercapto-purin-9-yl)-D-1,4-anhydro-ribit；(2R,3S,4R,5R)-2-(hydroxymethyl)-5-(2-methylsulfanylpurin-9-yl)tetrahydrofuran-3,4-diol；(2R,3S,4R,5R)-2-(hydroxymethyl)-5-(2-methylsulfanylpurin-9-yl)oxolane-3,4-diol
• CAS: 27640-80-8
• 化学式: C₁₁H₁₄N₄O₄S
• 分子量: 298.323
• InChiKey: AQBXLSVGUYASIQ-FDDDBJFASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  139
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2-MeS-nebularine 在 oxone 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 27.0h， 生成 2-cyano-9-β-D-ribofuranosylpurine
  参考文献：
  名称：

  Sulfone of the antibiotic, nebularine: synthesis and conversion to novel analogues of nebularlne

  摘要：

  DOI：

  10.1016/s0040-4020(01)86068-3
• 作为产物：
  描述：

  2-methylmercapto-9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)purine 在 sodium methylate 、 氯化铵 作用下， 生成 2-MeS-nebularine
  参考文献：
  名称：

  Sulfone of the antibiotic, nebularine: synthesis and conversion to novel analogues of nebularlne

  摘要：

  DOI：

  10.1016/s0040-4020(01)86068-3

文献信息

• Investigations into the Origin of the Molecular Recognition of Several Adenosine Deaminase Inhibitors
  作者：Irina Gillerman、Bilha Fischer

  DOI：10.1021/jm101286g

  日期：2011.1.13

  Inhibitors of adenosine deaminase (ADA, EC 3 5 4 4) are potential therapeutic agents for the treatment of various health disorders Several highly potent inhibitors were previously identified, yet they exhibit unacceptable toxicities We performed a SAR study involving a series of C2 or C8 substituted purine-riboside analogues with a view to discover less potent inhibitors with a lesser toxicity We found that any substitution at C8 position of nebularine resulted in total loss of activity toward calf intestinal ADA However several 2-substituted-adenosine, 8-aza-adenosine, and nebularine analogues exhibited inhibitory activity Specifically, 2-Cl-purine riboside, 8-aza-2-thiohexyl adenosine, 2-thiohexyl adenosine, and 2-MeS-purine riboside were found to be competitive inhibitors of ADA with K-i values of 25, 22, 6, and 3 mu M, respectively We concluded that electronic parameters are not major recognition determinants of ADA but rather steric parameters A C2 substituent which fits ADA hydrophobic pocket and improves H-bonding with the enzyme makes a good inhibitor In addition, a gg rotamer about C4'-C5' bond is apparently an important recognition determinant
• Synthesis of Potential Anticancer Agents. XV. Ribonucleosides of 2-Substituted Purines
  作者：Howard J. Schaeffer、H. Jeanette Thomas

  DOI：10.1021/ja01551a033

  日期：1958.9
• NAIR, VASU;HETTRICK, BRIAN J., TETRAHEDRON, 44,(1988) N 23, C. 70001-7006
  作者：NAIR, VASU、HETTRICK, BRIAN J.

  DOI：——

  日期：——
• Sulfone of the antibiotic, nebularine: synthesis and conversion to novel analogues of nebularlne
  作者：Vasu Nair、Brian J. Hettrick

  DOI：10.1016/s0040-4020(01)86068-3

  日期：1988.1