5'-O-[N-(N-L-phenylalanyl)-L-phenylalanyl]-sulfamoyladenosine | 1122490-04-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 5'-O-[N-(N-L-phenylalanyl)-L-phenylalanyl]-sulfamoyladenosine
• 英文别名: (1Z,2S)-N-[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxysulfonyl]-2-[[(2S)-2-azaniumyl-3-phenylpropanoyl]amino]-3-phenylpropanimidate
• CAS: 1122490-04-3
• 化学式: C₂₈H₃₂N₈O₈S
• 分子量: 640.677
• InChiKey: OKBOXHMCJGBGJQ-NHLIPTLUSA-N

物化性质

• 密度：
  1.64±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  45
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  255
• 氢给体数：
  6
• 氢受体数：
  13

反应信息

• 作为产物：
  描述：

  2',3'-di-O-(tert-butyldimethylsilyl)-5'-O-[N-[N-(N-Boc-L-phenylalanyl)-L-phenylalanyl]-sulfamoyl]adenosine triethylamine salt 在 三氟乙酸 、 三乙胺 、 triethylamine tris(hydrogen fluoride) 作用下， 以 水 、 乙醇 、 四氢呋喃 为溶剂， 反应 2.0h， 以47%的产率得到5'-O-[N-(N-L-phenylalanyl)-L-phenylalanyl]-sulfamoyladenosine
  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

文献信息

• Solid-Phase Synthesis of 5′-O-[N-(Acyl)sulfamoyl]adenosine Derivatives
  作者：Itedale Namro Redwan、Hanna Jacobson Ingemyr、Thomas Ljungdahl、Christopher P. Lawson、Morten Grøtli

  DOI：10.1002/ejoc.201200329

  日期：2012.7

  The solid-phase synthesis of 5'-O-[N-(acyl)sulfamoyl]adenosine derivatives is described. The use of a Rink amide polystyrene solid support together with an appropriately protected ribo-purine starting material allowed for the development of a highly reliable and practical route for the solid-phase synthesis of 5'-O-[N-(acyl)sulfamoyl]adenosines. The developed procedure enables the efficient parallel

  描述了 5'-O-[N-（酰基）氨磺酰基] 腺苷衍生物的固相合成。使用 Rink 酰胺聚苯乙烯固体载体和适当保护的核糖嘌呤起始材料，为 5'-O-[N-(酰基)氨磺酰基]的固相合成开发了一种高度可靠和实用的路线腺苷。开发的程序能够以高产率高效并行合成目标化合物。这些化合物是酰基腺苷酸的不可水解等排体，它们在一系列不同的代谢途径中发挥重要作用，例如核糖体和非核糖体肽合成、脂肪酸氧化或酶调节；一些形成腺苷酸的酶是潜在的药物靶点。
• Antibacterial 5′-O-(N-dipeptidyl)-sulfamoyladenosines
  作者：P. Van de Vijver、G.H.M. Vondenhoff、S. Denivelle、J. Rozenski、J. Verhaegen、A. Van Aerschot、P. Herdewijn

  DOI：10.1016/j.bmc.2008.11.054

  日期：2009.1

  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.