N-(octa-O-acetyllactobionyl)-2-methyl-2-hydroxylaminopropionamide | 950491-34-6

• 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: N-(octa-O-acetyllactobionyl)-2-methyl-2-hydroxylaminopropionamide
• 英文别名: [(2R,3S,4S,5R,6S)-3,4,5-triacetyloxy-6-[(2R,3R,4S,5R)-1,2,4,5-tetraacetyloxy-6-[[2-(hydroxyamino)-2-methylpropyl]amino]-6-oxohexan-3-yl]oxyoxan-2-yl]methyl acetate
• CAS: 950491-34-6
• 化学式: C₃₂H₄₈N₂O₂₀
• 分子量: 780.735
• InChiKey: NKKFUECWZHDJPG-OSSOYYLPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.5
• 重原子数：
  54
• 可旋转键数：
  27
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  290
• 氢给体数：
  3
• 氢受体数：
  21

反应信息

• 作为反应物：
  描述：

  N-(4-formylbenzyl)octanamide 、 N-(octa-O-acetyllactobionyl)-2-methyl-2-hydroxylaminopropionamide 以 四氢呋喃 、 溶剂黄146 为溶剂， 生成 1-(3-methylenedecyl)-4-((7R,8S,9R,10S)-3,3,13-trimethyl-7,8,10-tris(2-methylallyl)-2,6-dimethylene-9-(((1S,2S,3S,4S,5S)-2,3,4-tris(2-methylallyl)-5-(3-methylbut-3-en-1-yl)cyclohexyl)methyl)-2l5-tetradeca-1,13-dien-1-yl)benzene
  参考文献：
  名称：

  NOVEL AMPHIPHILIC DERIVATIVES OF ALPHA-C-PHENYL-N-TERT-BUTYLNITRONE

  摘要：

  从α-C-苯基-N-叔丁基亚甲基腈衍生的化合物，其制备方法以及用于制备用于预防或治疗与氧化应激相关疾病的药物的用途。

  公开号：

  US20090306001A1
• 作为产物：
  描述：

  [(2R,3S,4S,5R,6S)-3,4,5-triacetyloxy-6-[(2R,3R,4S,5R)-1,2,4,5-tetraacetyloxy-6-[(2-methyl-2-nitropropyl)amino]-6-oxohexan-3-yl]oxyoxan-2-yl]methyl acetate 在 氯化铵 、 锌 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 N-(octa-O-acetyllactobionyl)-2-methyl-2-hydroxylaminopropionamide
  参考文献：
  名称：

  NOVEL AMPHIPHILIC DERIVATIVES OF ALPHA-C-PHENYL-N-TERT-BUTYLNITRONE

  摘要：

  从α-C-苯基-N-叔丁基亚甲基腈衍生的化合物，其制备方法以及用于制备用于预防或治疗与氧化应激相关疾病的药物的用途。

  公开号：

  US20090306001A1

文献信息

• Cholesterol-based α-phenyl-N-tert-butyl nitrone derivatives as antioxidants against light-induced retinal degeneration
  作者：Fanny Choteau、Grégory Durand、Isabelle Ranchon-Cole、Christine Cercy、Bernard Pucci

  DOI：10.1016/j.bmcl.2010.10.037

  日期：2010.12

  cholesterol-based α-phenyl-N-tert-butyl nitrone derivatives were synthesized as antioxidants against light-induced retinal degeneration. Whereas nitrone 10 significantly protected retina against bright fluorescent light exposure when injected into the vitreous at 1 mM, no protection was observed with nitrone 6. The parent compound α-phenyl-N-tert-butyl nitrone also exhibited protective activity at 9 mM

  两个基于胆固醇-α苯基ñ -叔丁基硝酮衍生物的合成作为针对光诱导的视网膜变性的抗氧化剂。当硝酮10以1 mM的剂量注入玻璃体时，可显着保护视网膜免受明亮的荧光照射，而硝酮6则未观察到保护作用。母体化合物α苯基ñ -叔丁基硝酮也为9mm表现出保护活性但不能以1毫米。这表明硝酮10可能是治疗视网膜疾病的候选药物。
• Amphiphilic Amide Nitrones: A New Class of Protective Agents Acting as Modifiers of Mitochondrial Metabolism
  作者：Grégory Durand、Burkhard Poeggeler、Stéphanie Ortial、Ange Polidori、Frederick A. Villamena、Jutta Böker、Rüdiger Hardeland、Miguel A. Pappolla、Bernard Pucci

  DOI：10.1021/jm100212x

  日期：2010.7.8

  Our group has demonstrated that the amphiphilic character of alpha-phenyl-N-tert-butyl nitrone based agents is a key feature in determining their bioactivity and protection against oxidative toxicity. In this work, we report the synthesis of a new class of amphiphilic amide nitrones. Their hydroxyl radical scavenging activity and radical reducing potency were shown using ABTS competition and ABTS(center dot+) reduction assays, respectively. Cyclic voltammetry was used to investigate their redox behavior, and the effects of the substitution of the PBN on the charge density of the nitronyl atoms, the electron affinity, and the ionization potential were computationally rationalized. The protective effects of amphiphilic amide nitrones in cell cultures exposed to oxidotoxins greatly exceeded those exerted by the parent compound PBN. They decreased electron and proton leakage as well as hydrogen peroxide formation in isolated rat brain mitochondria at nanomolar concentration. They also significantly enhanced mitochondrial membrane potential. Finally, dopamine-induced inhibition of complex I activity was antagonized by pretreatment with these agents. These findings indicate that amphiphilic amide nitrones are much more than just radical scavenging antioxidants but may act as a new class of bioenergetic agents directly on mitochondrial electron and proton transport.