N-(pyridin-4-ylmethylene)aniline oxide | 20147-42-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: N-(pyridin-4-ylmethylene)aniline oxide
• 英文别名: N-phenyl-α-(4-pyridyl)-nitrone；4-pyridyl-N-phenylnitrone；N-pyridin-4-ylmethylene-aniline N-oxide；N-phenyl-1-pyridin-4-ylmethanimine oxide
• CAS: 20147-42-6
• 化学式: C₁₂H₁₀N₂O
• mdl: MFCD00449235
• 分子量: 198.224
• InChiKey: LJAZWXXSTFVHRG-UHFFFAOYSA-N

物化性质

• 沸点：
  380.1±34.0 °C(Predicted)
• 密度：
  1.193±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  41.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(pyridin-4-ylmethylene)aniline oxide 在 sodium tetrahydroborate 、 copper(l) iodide 、 水 、 三乙胺 、 lithium hydroxide 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 31.0h， 生成 trans-3-(hydroxymethyl)-1-phenyl-4-(4-pyridyl)-2-azetidinone
  参考文献：
  名称：

  Design, synthesis and characterization of dual inhibitors against new targets FabG4 and HtdX of Mycobacterium tuberculosis

  摘要：

  Herein, we present dual inhibitors of new targets FabG4 and HtdX for the first time. In this work, eight compounds have been designed, synthesized, characterized and evaluated for bio-activities. Amongst them, six compounds have shown inhibitory activities. Three of them (12-14) demonstrate dual inhibition of both FabG4 and HtdX at low micromolar concentration. In addition, the dual inhibitors show good anti-mycobacterial properties against both planktonic growth and biofilm culture of Mycobacterium species. This study is an important addition to tuberculosis drug discovery because it explores two new enzymes as drug targets and presents their dual inhibitors as good candidates for pre-clinical trials. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.06.007
• 作为产物：
  描述：

  硝基苯 在 氯化铵 、 锌 作用下， 以 甲醇 、 水 为溶剂， 反应 12.25h， 生成 N-(pyridin-4-ylmethylene)aniline oxide
  参考文献：
  名称：

  Design, synthesis and characterization of dual inhibitors against new targets FabG4 and HtdX of Mycobacterium tuberculosis

  摘要：

  Herein, we present dual inhibitors of new targets FabG4 and HtdX for the first time. In this work, eight compounds have been designed, synthesized, characterized and evaluated for bio-activities. Amongst them, six compounds have shown inhibitory activities. Three of them (12-14) demonstrate dual inhibition of both FabG4 and HtdX at low micromolar concentration. In addition, the dual inhibitors show good anti-mycobacterial properties against both planktonic growth and biofilm culture of Mycobacterium species. This study is an important addition to tuberculosis drug discovery because it explores two new enzymes as drug targets and presents their dual inhibitors as good candidates for pre-clinical trials. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.06.007

文献信息

• A green synthesis of nitrones in glycerol
  作者：Monire Shariatipour、Masoumeh Jadidinejad、Akbar Heydari

  DOI：10.1007/s12039-019-1677-7

  日期：2019.10

  AbstractAn eco-friendly and efficient synthesis of nitrones is presented by condensation of an equimolar amount of aldehydes and N-substituted hydroxylamine hydrochlorides in glycerol as a recyclable solvent-catalyst. This novel protocol provides rapid and mild access to a series of nitrone derivatives in good to excellent yields in the absence of catalyst and base. Graphic abstractSYNOPSIS In this

  摘要通过将等摩尔量的醛和N-取代的羟胺盐酸盐在甘油中作为可循环利用的溶剂催化剂进行缩合，提出了一种环保，高效的硝酮合成方法。在没有催化剂和碱的情况下，这种新颖的方法可以快速温和地获得一系列硝酮衍生物，收率好至极好。 图形摘要提要在这项研究中，使用甘油作为溶剂催化剂的无碱方案被用于醛和N-取代的羟胺盐酸盐的缩合反应的环保合成硝酮。 醛与N-取代的羟胺盐酸盐在甘油中的缩合
• <i>α</i>-(Trifluoromethyl)amine Derivatives via Nucleophilic Trifluoromethylation of Nitrones
  作者：Derek W. Nelson、James Owens、Diana Hiraldo

  DOI：10.1021/jo000685l

  日期：2001.4.1

  (Trifluoromethyl)trimethylsilane (TMSCF(3)) reacts with nitrones to afford alpha-(trifluoromethyl)hydroxylamines protected as O-trimethylsilyl ethers. Potassium t-butoxide initiates the nucleophilic trifluoromethylation. The reaction works best with alpha,N-diaryl nitrones, and the conditions are compatible with a range of substituents on the aryl groups. Acidic deprotection of the nitrone/TMSCF(3)

  （三氟甲基）三甲基硅烷（TMSCF（3））与硝酮反应，得到保护为O-三甲基甲硅烷基醚的α-（三氟甲基）羟胺。叔丁醇钾引发亲核三氟甲基化。该反应与α，N-二芳基硝酮最有效，并且条件与芳基上的一系列取代基相容。硝酸/ TMSCF（3）加合物的酸性脱保护生成α-（三氟甲基）羟胺。加合物的催化氢化产生α-（三氟甲基）胺。在α-芳基环或杂环α-芳基上具有强吸电子基团的Nitrone / TMSCF（3）加合物经历消除/加成序列以生成α，α-双（三氟甲基）胺。烷基直接与1,3-偶极部分结合的亚硝基无法与TMSCF（3）反应，
• Synthesis of novel spiro-isoxazoline and spiro-isoxazolidine derivatives of tomentosin
  作者：Mohamed Zaki、Abdelouahd Oukhrib、Mohamed Akssira、Sabine Berteina-Raboin

  DOI：10.1039/c6ra25869g

  日期：——

  A series of novel enantiomerically pure spiro-isoxazolidines and spiro-isoxazolines were synthesized regioselectively by 1,3-dipolar cycloaddition using respectively two dipoles, nitrones and nitrile oxides, on the exocyclic double bond of the B ring of tomentosin (α-methylene-γ-butyrolactone), a sesquiterpene lactone extracted from Dittrichia viscosa.

  通过1,3-偶极环加成反应，分别在绒毛膜球蛋白B环（α-亚甲基-γ -丁内酯），一种从粘菌（Dittrichia viscosa）中提取的倍半萜烯内酯。
• Effect of substituents on spin density in benzimidazole nitronyl nitroxide radicals studied by electron spin resonance
  作者：Burak Esat、Ismail Fidan、Sumeyye Bahceci、Yusuf Yerli、Levent Sari

  DOI：10.1002/mrc.2443

  日期：2009.8

  Several novel benzimidazole‐3‐oxide‐1‐oxyl radicals with substituents at 5 and/or 6 position were synthesized. The ESR analysis of nitrogen hyperfine coupling constants (hfccs) revealed that substituents at 5 and 6‐position affect the spin density to greater extent than substituents on the phenyl ring at 2‐position. Density functional theory calculations of nitrogen hfccs were performed using several

  合成了几种在 5 和/或 6 位具有取代基的新型苯并咪唑-3-氧化物-1-氧基。氮超精细耦合常数（hfccs）的 ESR 分析表明，5 位和 6 位的取代基比 2 位苯环上的取代基对自旋密度的影响更大。氮 hfccs 的密度泛函理论计算是使用几种不同的 Pople 型基组，以及局部轨道（IGLO-II、IGLO-III）和电子顺磁共振（EPR-II、EPR- II) 基组。实验和理论 hfcc 进行了比较。版权所有 © 2009 John Wiley & Sons, Ltd.
• 1,2,4-Oxadiazole-5-ones as analogues of tamoxifen: synthesis and biological evaluation
  作者：Maria A. Chiacchio、Laura Legnani、Agata Campisi、Bottino Paola、Lanza Giuseppe、Daniela Iannazzo、Lucia Veltri、Salvatore Giofrè、Roberto Romeo

  DOI：10.1039/c9ob00651f

  日期：——

  A series of 2,3,4-triaryl-substituted 1,2,4-oxadiazole-5-ones have been prepared as fixed-ring analogues of tamoxifen (TAM), a drug inhibitor of Estradiol Receptor (ER) used in breast cancer therapy, by an efficient synthetic protocol based on a 1,3-dipolar cycloaddition of nitrones to isocyanates. Some of the newly synthesized compounds (14d-f, 14h and 14k) show a significant cytotoxic effect in a

  已经制备了一系列2,3,4-三芳基取代的1,2,4-恶二唑-5-酮作为他莫昔芬（TAM）的固定环类似物，他莫昔芬是用于乳腺癌的雌二醇受体（ER）的药物抑制剂通过基于硝酮与异氰酸酯的1,3-偶极环加成反应的高效合成方案进行治疗。一些新合成的化合物（14d-f，14h和14k）在具有50.63至31.82μM的IC50值的人乳腺癌细胞系（MCF-7）中显示出明显的细胞毒性作用。另外，化合物14d-f，14h和14k能够增加p53表达水平，也激活细胞凋亡途径。在ER的晶体结构上进行的新型化合物的分子建模研究表明，与TAM相似，与配体的芳环之间存在强烈的疏水相互作用。这些数据表明1,2，