α-(3-indolyl) N-phenyl nitrone | 84186-34-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: α-(3-indolyl) N-phenyl nitrone
• 英文别名: C-(3-indolyl)-N-phenylnitrone
• CAS: 84186-34-5
• 化学式: C₁₅H₁₂N₂O
• 分子量: 236.273
• InChiKey: PUFQWQGWOHQZDQ-UHFFFAOYSA-N

物化性质

• 熔点：
  172 °C
• 沸点：
  480.0±37.0 °C(Predicted)
• 密度：
  1.275±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.43
• 重原子数：
  18.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  41.86
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  α-(3-indolyl) N-phenyl nitrone 在 palladium 10% on activated carbon 、 甲酸铵 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 0.08h， 生成 butyl 2-hydroxy-4-(1H-indol-3-yl)butanoate
  参考文献：
  名称：

  吲哚基-异唑烷的形成和还原性开环反应：获得新型天然产物类似物和前体

  摘要：

  的区域选择性和立体选择性的1,3-偶极环加成Ç - - （3-吲哚基）ñ -phenylnitrone（2用variedly取代dipolarophiles被执行以获得）顺式- C4和C5取代的吲哚基-异恶唑烷6A-C和7A-F， 分别。通过使用各种还原剂还原获得的异恶唑烷，会导致N–O键断裂，同时伴随C–N键断裂，从而导致形成基于吲哚的新型天然产物类似物和前体。

  DOI：

  10.1016/j.tet.2015.12.032
• 作为产物：
  描述：

  硝基苯 在 氯化铵 、 锌 作用下， 以 乙醇 为溶剂， 生成 α-(3-indolyl) N-phenyl nitrone
  参考文献：
  名称：

  An Unexpected Catalytic Synthesis of Novel and Known Bis(Pyrazolyl) Methanes by the use of α-aryl-N-phenyl Nitrones in Aqueous Media

  摘要：

  在一定量的硅钨酸催化下，在 EtOH/H2O 溶液中，芳基 N-苯基硝基腈与 3-甲基-1-苯基-2-吡唑啉-5-酮反应，意外地得到了高产率的双(3-羟基-1-苯基吡唑基)芳基甲烷，而不是两种可能的 1,3-加成产物。这是首次报道通过硝基化合物和吡唑啉-5-酮反应合成双（3-羟基-1-苯基吡唑基）芳基甲烷。文中提出了这一过程的可能机理。

  DOI：

  10.3184/174751914x14114871789226

文献信息

• Formation and reductive ring opening reactions of indolyl bicyclic-isoxazolidines-II:7 access to novel natural product analogs
  作者：Gagandeep Singh、Tilak Raj、Vivek Gupta、Mohan Paul Singh Ishar

  DOI：10.1016/j.tetlet.2016.09.011

  日期：2016.10

  Attempted reductive cleavage of indolyl-bicyclic-isoxazolidines (4a,b; R = benzyl, phenyl) with ammonium formate, methanol-THF solvents, at ambient temperature, in the presence of Pd/C lead to facile synthesis of indolyl-α-hydroxy-γ-lactams (5a–b), derived from reductive cleavage of the NO bond of bicyclic-isoxazolidines, followed by intramolecular recyclization. On the other hand, reaction of 4c (R = ethyl)

  在环境温度下，在Pd / C存在下，尝试用甲酸铵，甲醇-THF溶剂还原吲哚基-双环-异恶唑烷（4a，b； R =苄基，苯基），导致容易合成吲哚基-α-羟基-γ-内酰胺（5a – b），源自双环异恶唑烷的N O键的还原性裂解，然后进行分子内环化。另一方面，在相同条件下4c（R =乙基）的反应遵循不同的过程，从而得到6，这是天然存在的海洋生物碱-皂素的类似物。提供了由DFT计算支持的观察到的反应行为的机械原理。
• Investigations on synthesis of indole based constrained mimetic scaffolds through 1,3-dipolar cycloadditions of the C-(3-indolyl)-N-phenylnitrone with a variety of olefinic and allenic dipolarophiles under microwave irradiation
  作者：Surinderjit Singh Bhella、Ajay Pal Singh Pannu、Munusamy Elango、Ashish Kapoor、Maninder Singh Hundal、Mohan Paul S. Ishar

  DOI：10.1016/j.tet.2009.05.093

  日期：2009.8

  3-dipolar cycloadditions of C-(3-indolyl)-N-phenylnitrone (19) with a number of olefinic dipolarophiles (20a–f) afford isoxazolidines (21–26) in high yields, which are conformationally constrained mimetics of indole-3-propionic acid of biological significance. Similar cycloadducts derived from addition of nitrone (19) to allenic esters (27a–c) undergo domino reorganization to afford potentially biologically

  单模微波辅助的区域选择性和立体选择性的1,3-偶极环加成Ç - （3-吲哚基） - ñ -phenylnitrone（19）具有多个烯属dipolarophiles（的20A - ˚F）得到异恶唑烷（21 - 26高）产率，其为具有生物学意义的吲哚-3-丙酸的构象约束模拟物。从另外的硝酮（衍生类似cycloadducts 19），以丙二烯酯（27A - C ^）经历多米诺重组，得到潜在生物活性双吲哚衍生物（28，29）。除其他方面外，根据HOMO-偶极-LUMO-偶极亲和物分析了观察到的区域和立体选择性，并在过渡态介入这些环加成过程中涉及了次级轨道/空间相互作用。
• Copper-Catalyzed Synthesis of Polysubstituted Pyrroles through [3+1+1] Cycloaddition Reaction of Nitrones and Isocyanides
  作者：Zhuang Tian、Jiaojiao Xu、Bingxin Liu、Qitao Tan、Bin Xu

  DOI：10.1021/acs.orglett.8b00798

  日期：2018.5.4

  An efficient, copper-catalyzed [3+1+1] cycloaddition reaction was developed for the expedient synthesis of pharmacologically interesting polysubstituted pyrroles from easily available nitrones and α-acidic isocyanides. The given approach features a new mode of cycloaddition between nitrones and isocyanides with wide substrate scope, good functional group tolerance, and operational simplicity. The operando

  开发了一种有效的铜催化的[3 + 1 + 1]环加成反应，用于从易于获得的硝酮和α-酸性异氰酸酯方便地合成药理学上有趣的多取代吡咯。给定的方法具有在硝酮和异氰酸酯之间进行环加成的新模式，具有广泛的底物范围，良好的官能团耐受性和操作简便性。操作红外光谱用于反应中间体的表征。
• The stereoselective synthesis of highly functionalized tertiary 3-aminoindoles/anilines or dihydropyrroles from C-(3-indolyl)-N-aryl and C,N-diaryl nitrones
  作者：V.S. Velezheva、V.N. Azev、A.G. Kornienko、A.S. Peregudov、I.A. Godovikov、Yu. L. Sebyakin

  DOI：10.1016/j.tetlet.2010.10.045

  日期：2010.12

  We report on the novel properties of nitrones including their transformations via reactions with sodium malonates to give functionalized stereodefined derivatives of tertiary 3-aminoindoles or anilines, as well as fully-substituted dihydropyrroles. The outcome of the reactions is dependent mainly upon the nature of the starting C-nitrone substituent and solvent used. The formation of a new carbon nitrogen bond in the obtained amines occurs via a nucleophilic 1,2-aryl/3-indolyl shift from C to the adjacent nitrogen. (C) 2010 Elsevier Ltd. All rights reserved.
• Indolyl-isoxazolidines attenuate LPS-stimulated pro-inflammatory cytokines and increase survival in a mouse model of sepsis: Identification of potent lead
  作者：Gagandeep Singh、Gurjit Singh、Rajbir Bhatti、Mehak Gupta、Ajay Kumar、Ankita Sharma、Mohan Paul Singh Ishar

  DOI：10.1016/j.ejmech.2018.04.004

  日期：2018.6

  A library of indolyl-isoxazolidines (6-9) has been synthesized by regio- and stereoselective microwave irradiated 1,3-dipolar cycloadditions of C-(3-indolyl)-N-phenylnitrone (2') with variedly substituted dipolarophiles (3'-5') and screened for their anti-inflammatory activities through inhibition of pro inflammatory cytokines such as TNF-alpha and IL-6. Amongst the evaluated compounds (6-9), bicyclic isoxazolidine (9a) was found to exhibit significant inhibitory potential against LPS induced human IL-6 and TNF-alpha in THP-1 cells. Compound 9a was further assessed for in vivo analgesic and anti-inflammatory activities via acetic acid induced writhing and carrageenan induced paw edema models in mice, respectively. The results showed that compound possesses potent anti-inflammatory-analgesic activity comparable to indomethacin and did not show toxicity up to a 2000 mg kg(-1) dose as evidenced by histopathological studies. Consequently, the most active compound 9a was also evaluated against LPS-induced septic death and exhibited a significant protection in in vivo mouse model. Taken all together, the results suggest that the compound 9a is able to attenuate pro-inflammatory cytokines such as IL-6 and TNF-alpha; accelerate resolution of inflammation, and also increased survival rate of septic mice. Therefore, these "lead" isoxazolidines can be used as promising candidate for further analgesic/anti-inflammatory drug design and development. (C) 2018 Elsevier Masson SAS. All rights reserved.