5'-O-[N-(N-L-methionyl)-L-alanyl]-sulfamoyladenosine triethylamine salt | 1122490-47-4

• 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-L-methionyl)-L-alanyl]-sulfamoyladenosine triethylamine salt
• CAS: 1122490-47-4
• 化学式: C₆H₁₅N*C₁₈H₂₈N₈O₈S₂
• 分子量: 649.793
• InChiKey: XVDZDNIBBFZZSR-YNEALHHZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.66
• 重原子数：
  43.0
• 可旋转键数：
  14.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  250.14
• 氢给体数：
  6.0
• 氢受体数：
  16.0

反应信息

• 作为产物：
  描述：

  ((2R,3R,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-bis((tert-butyldimethylsilyl)oxy)tetrahydrofuran-2-yl)methyl sulfamate 在 1-羟基苯并三唑 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三氟乙酸 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 5'-O-[N-(N-L-methionyl)-L-alanyl]-sulfamoyladenosine triethylamine salt
  参考文献：
  名称：

  Antibacterial 5′-O-(N-dipeptidyl)-sulfamoyladenosines

  摘要：

  The aminoacyl-tRNA synthetase (aaRS) class of enzymes is a validated target for antimicrobial development. Aminoacyl analogues of 5'-O-(N-L-aminoacyl)-sulfamoyladenosines are known to be potent inhibitors of aaRS, but whole cell antibacterial activity of these compounds is very limited, and poor penetration into bacteria has been proposed as the main reason for this. Aiming to find derivatives that better penetrate bacteria, we developed a simple and short method to prepare dipeptidyl-derivatives of 5'-O-(N-L-aminoacyl)-sulfamoyladenosines, and used this method to prepare 18 5'-O-(N-dipeptidyl)-sulfamoyladenosines. The antibacterial activity of these derivatives and a number of reference compounds against S. aureus, E. faecalis and E. coli was determined. Several of the new derivatives showed improved antibacterial activity and an altered spectrum of antibacterial activity. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.11.054