9H-fluoren-9-ylmethyl N-[(2S)-1-[[(2R)-2,3-dinitrooxypropyl]amino]-1-oxo-3-(1-tritylimidazol-4-yl)propan-2-yl]carbamate | 1392505-91-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 9H-fluoren-9-ylmethyl N-[(2S)-1-[[(2R)-2,3-dinitrooxypropyl]amino]-1-oxo-3-(1-tritylimidazol-4-yl)propan-2-yl]carbamate
• CAS: 1392505-91-7
• 化学式: C₄₃H₃₈N₆O₉
• 分子量: 782.81
• InChiKey: JSEFVILIJIMXGI-IKCXEYKWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.9
• 重原子数：
  58
• 可旋转键数：
  16
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  195
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  9H-fluoren-9-ylmethyl N-[(2S)-1-[[(2R)-2,3-dinitrooxypropyl]amino]-1-oxo-3-(1-tritylimidazol-4-yl)propan-2-yl]carbamate 在 哌啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 [(2R)-1-[[(2S)-2-amino-3-(1-tritylimidazol-4-yl)propanoyl]amino]-3-nitrooxypropan-2-yl] nitrate
  参考文献：
  名称：

  Carnosine analogues containing NO-donor substructures: Synthesis, physico-chemical characterization and preliminary pharmacological profile

  摘要：

  The synthesis, physico-chemical, and biological characterisation of a short series of carnosine amides bearing NO-donor nitrooxy functionalities are described. The NO-donor carnosine analogues and their des-NO derivatives display carnosine-like properties, differing from the lead for their high serum stability. The newly-synthesised compounds are able to complex Cu2+ ions at physiological pH, displaying significant copper ion sequestering ability, and protect LDL from oxidation catalysed by Cu2+ ions. All products show moderately-potent HNE quenching activity. The NO-donor compounds 7c-f relaxed rat aorta strips via an NO-dependent mechanism. In vivo evaluation of organ protection in a model of cerebral ischaemia/reperfusion injury, using the selected NO-donor 7e and its des-NO analogue 7a, showed that both derivatives protect from hypoxia-induced brain damage, at lower concentrations than carnosine: 7e also decreased serum TNF-alpha levels. This class of NO-donor carnosine amides is worthy of further study as potential tools for treating a wide range of chronic vascular and neurodegenerative diseases in which NO-bioavailability is reduced. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.04.032
• 作为产物：
  描述：

  (2R)-2,3-(dinitrooxy)propan-1-ammonium nitrate 、 N-Fmoc-N'-三苯甲基-L-组氨酸 在 1-羟基苯并三唑 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 反应 0.17h， 生成 9H-fluoren-9-ylmethyl N-[(2S)-1-[[(2R)-2,3-dinitrooxypropyl]amino]-1-oxo-3-(1-tritylimidazol-4-yl)propan-2-yl]carbamate
  参考文献：
  名称：

  Carnosine analogues containing NO-donor substructures: Synthesis, physico-chemical characterization and preliminary pharmacological profile

  摘要：

  The synthesis, physico-chemical, and biological characterisation of a short series of carnosine amides bearing NO-donor nitrooxy functionalities are described. The NO-donor carnosine analogues and their des-NO derivatives display carnosine-like properties, differing from the lead for their high serum stability. The newly-synthesised compounds are able to complex Cu2+ ions at physiological pH, displaying significant copper ion sequestering ability, and protect LDL from oxidation catalysed by Cu2+ ions. All products show moderately-potent HNE quenching activity. The NO-donor compounds 7c-f relaxed rat aorta strips via an NO-dependent mechanism. In vivo evaluation of organ protection in a model of cerebral ischaemia/reperfusion injury, using the selected NO-donor 7e and its des-NO analogue 7a, showed that both derivatives protect from hypoxia-induced brain damage, at lower concentrations than carnosine: 7e also decreased serum TNF-alpha levels. This class of NO-donor carnosine amides is worthy of further study as potential tools for treating a wide range of chronic vascular and neurodegenerative diseases in which NO-bioavailability is reduced. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.04.032

文献信息

• Carnosine analogues containing NO-donor substructures: Synthesis, physico-chemical characterization and preliminary pharmacological profile
  作者：Massimo Bertinaria、Barbara Rolando、Marta Giorgis、Gabriele Montanaro、Elisabetta Marini、Massimo Collino、Elisa Benetti、Pier Giuseppe Daniele、Roberta Fruttero、Alberto Gasco

  DOI：10.1016/j.ejmech.2012.04.032

  日期：2012.8

  The synthesis, physico-chemical, and biological characterisation of a short series of carnosine amides bearing NO-donor nitrooxy functionalities are described. The NO-donor carnosine analogues and their des-NO derivatives display carnosine-like properties, differing from the lead for their high serum stability. The newly-synthesised compounds are able to complex Cu2+ ions at physiological pH, displaying significant copper ion sequestering ability, and protect LDL from oxidation catalysed by Cu2+ ions. All products show moderately-potent HNE quenching activity. The NO-donor compounds 7c-f relaxed rat aorta strips via an NO-dependent mechanism. In vivo evaluation of organ protection in a model of cerebral ischaemia/reperfusion injury, using the selected NO-donor 7e and its des-NO analogue 7a, showed that both derivatives protect from hypoxia-induced brain damage, at lower concentrations than carnosine: 7e also decreased serum TNF-alpha levels. This class of NO-donor carnosine amides is worthy of further study as potential tools for treating a wide range of chronic vascular and neurodegenerative diseases in which NO-bioavailability is reduced. (C) 2012 Elsevier Masson SAS. All rights reserved.