2',3'-di-O-(tert-butyldimethylsilyl)-5'-O-[N-(N-Boc-L-tryptophanyl)-sulfamoyl]adenosine triethylamine salt | 1122489-75-1

• 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',3'-di-O-(tert-butyldimethylsilyl)-5'-O-[N-(N-Boc-L-tryptophanyl)-sulfamoyl]adenosine triethylamine salt
• CAS: 1122489-75-1
• 化学式: C₆H₁₅N*C₃₈H₆₀N₈O₉SSi₂
• 分子量: 962.371
• InChiKey: TVVJRBVIVYMATE-QLCLNGSXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.43
• 重原子数：
  65.0
• 可旋转键数：
  16.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.66
• 拓扑面积：
  227.14
• 氢给体数：
  4.0
• 氢受体数：
  15.0

反应信息

• 作为反应物：
  描述：

  2',3'-di-O-(tert-butyldimethylsilyl)-5'-O-[N-(N-Boc-L-tryptophanyl)-sulfamoyl]adenosine triethylamine salt 在 1-羟基苯并三唑 、 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-[Nα-(L-lysyl)-L-tryptophanyl]-sulfamoyl]-adenosine
  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
• 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 、 BOC-L-色氨酸羟基琥珀酰亚胺酯 、 三乙胺 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 silica gel 作用下， 以 N,N-二甲基甲酰胺 、 甲醇 、 二氯甲烷 为溶剂， 以97%的产率得到2',3'-di-O-(tert-butyldimethylsilyl)-5'-O-[N-(N-Boc-L-tryptophanyl)-sulfamoyl]adenosine 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