1-azido-2-methyl-2-nitropropane | 183577-96-0

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: 1-azido-2-methyl-2-nitropropane
• CAS: 183577-96-0
• 化学式: C₄H₈N₄O₂
• 分子量: 144.133
• InChiKey: ZLEVKDDEHLNHSM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  60.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-azido-2-methyl-2-nitropropane 在 三苯基膦 、 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 以87%的产率得到2-甲基-2-硝基丙胺
  参考文献：
  名称：

  离子和非离子两亲性α-苯基-N-叔丁基亚硝基衍生物的合成和初步生物学评估。

  摘要：

  在这项研究中，我们报告了一系列衍生自α-苯基-N-叔丁基硝基（PBN）的新型两亲化合物的合成。硝酮官能团装配在分子的极性和非极性基团之间的核心中。极性头由乳糖酸酰胺，铵或羧酸根基团组成。疏水部分由氢或全氟化碳链组成。使用氨基甲酸酯，硫醚或酰胺键将疏水链连接到PBN衍生物的叔丁基上。研究了这些不同参数对这些化合物的亲水亲脂平衡及其自旋捕集活性的影响。各种ESR测量表明PBN的芳族和叔丁基官能团不影响其自旋阱性能。而且，

  DOI：

  10.1021/jm030873e
• 作为产物：
  描述：

  methanesulphonic acid (2-methyl-2-nitropropyl)-ester 在 sodium azide 作用下， 以 二甲基亚砜 为溶剂， 以7.4g的产率得到1-azido-2-methyl-2-nitropropane
  参考文献：
  名称：

  三功能支架衍生化合物作为胰岛素受体调节剂的文库的合成和评价

  摘要：

  我们设计了三功能支架衍生化合物的组合库，这些化合物是用30种不同的内部叠氮化物衍生化的。建议该化合物模拟胰岛素分子中与胰岛素受体（IR）结合的表位，并结合并激活该受体。这项工作使我们能够测试我们的合成和生物学方法，并证明其对于三官能支架衍生化合物的固相合成和组合文库测试的稳健性和可靠性。我们的努力导致发现了两种化合物，它们能够弱诱导IR的自磷酸化并在0.1 mM浓度下弱结合至该受体。尽管取得了这些温和的生物学结果，这些结果充分证明了调节蛋白质间相互作用的众所周知的困难，这项研究代表了针对IR的独特例子，该IR是为这一目的专门设计和合成的一组非肽化合物。我们相信这项工作可以为基于支架结构的下一代胰岛素模拟物的开发打开新的视野。

  DOI：

  10.1021/acscombsci.6b00132

文献信息

• Novel ampiphilic derivatives of alpha-c-phenyl-n-tert-butyl nitrone
  申请人：Durand Gregory

  公开号：US20060120985A1

  公开（公告）日：2006-06-08

  Novel compounds, derivatives of α-C-phenylN-tert-butyl nitrone, a method for production and use thereof for the preparation of medicaments for the prevention or treatment of diseases related to oxidative stress.

  新化合物，α-C-苯基N-叔丁基亚硝基衍生物，其制备方法及用途，用于制备预防或治疗与氧化应激相关疾病的药物。
• NOVEL AMPHIPHILIC DERIVATIVES OF ALPHA-C-PHENYL-N-TERT-BUTYLNITRONE
  申请人：Durand Grégory

  公开号：US20090306001A1

  公开（公告）日：2009-12-10

  Compounds derived from α-C-phenyl-N-tert-butylnitrone, a process for the preparation thereof and use thereof for the preparation of medicaments for use in preventing or treating oxidative stress-related diseases.

  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。
• 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.
• Synthesis of a new family of glycolipidic nitrones as potential antioxidant drugs for neurodegenerative disorders
  作者：Grégory Durand、Ange Polidori、Jean-Pierre Salles、Bernard Pucci

  DOI：10.1016/s0960-894x(02)01079-x

  日期：2003.3

  This paper deals with the synthesis of a novel series of amphiphilic glycosylated spin-traps derived from alpha-Phenyl-N-tert-butyl nitrone (PBN) and an initial characterization of their anti-caspase-3 activity. Preliminary investigation of their anti-apoptosis effect showed they dramatically inhibit the activity of caspase-3 in cultured neuronal cells following induction of apoptosis by hydrogen peroxide. (C) 2003 Elsevier Science Ltd. All rights reserved.