5'-O-[N-(N-Boc-L-alanyl)sulfamoyl]-3'-O-(tertbutyldimethylsilyl)-2'-deoxy-2'-fluoroadennosine triethylamine salt | 1030372-05-4

• 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: 5'-O-[N-(N-Boc-L-alanyl)sulfamoyl]-3'-O-(tertbutyldimethylsilyl)-2'-deoxy-2'-fluoroadennosine triethylamine salt
• CAS: 1030372-05-4
• 化学式: C₆H₁₅N*C₂₄H₄₀FN₇O₈SSi
• 分子量: 734.965
• InChiKey: RJXCYYMJNYYMQJ-MWORYHAZSA-N

反应信息

• 作为反应物：
  描述：

  5'-O-[N-(N-Boc-L-alanyl)sulfamoyl]-3'-O-(tertbutyldimethylsilyl)-2'-deoxy-2'-fluoroadennosine triethylamine salt 在 三氟乙酸 作用下， 以 水 为溶剂， 反应 5.0h， 以46%的产率得到5'-O-[N-(L-alanyl)sulfamoyl]-2'-deoxy-2'-fluoroadenosine
  参考文献：
  名称：

  Aminoacyl-tRNA Synthetase Inhibitors as Potent and Synergistic Immunosuppressants

  摘要：

  The aminoacyl-tRNA synthetase family of enzymes is the target of many antibacterials and inhibitors of eukaryotic hyperproliferation. In screening analogues of 5'-O-(N-L-aminoacyl)-sulfamoyladenosine containing all 20 proteinogenic amino acids, we found these compounds to have potent immunosuppressive activity. Also, we found that combinations of these compounds inhibited the immune response synergistically. Based on these data, analogues with modifications at the aminoacyl and ribose moieties were designed and evaluated, and several of these showed high immunosuppressive potency, with one compound having an IC(50) of 80 nM, when tested in a cellular mixed lymphocyte reaction assay. Apart from showing the potential of aminoacyl-tRNA synthetase inhibitors as immunosuppressants, the current study also provides arguments for careful evaluation of the immunosuppressive activity of developmental antibacterials that target these enzymes.

  DOI：

  10.1021/jm8000746