ethyl 4-((4-methylbenzyl)amino)benzoate | 64261-06-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ethyl 4-((4-methylbenzyl)amino)benzoate
• 英文别名: Ethyl 4-[(4-methylphenyl)methylamino]benzoate
• CAS: 64261-06-9
• 化学式: C₁₇H₁₉NO₂
• 分子量: 269.343
• InChiKey: ILWXVDRCQOLGJH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 4-((4-methylbenzyl)amino)benzoate 在 吡啶 、 4-二甲氨基吡啶 、 lithium hydroxide monohydrate 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 36.0h， 生成 4-{N-[(4-methylphenyl)methyl]-4-methylbenzenesulfonamido}benzoic acid
  参考文献：
  名称：

  Discovery of a benzenesulfonamide-based dual inhibitor of microsomal prostaglandin E2 synthase-1 and 5-lipoxygenase that favorably modulates lipid mediator biosynthesis in inflammation

  摘要：

  Leukotrienes (LTs) and prostaglandin (PG)E-2, produced by 5-lipoxygenase (5-LO) and microsomal prostaglandin E-2 synthase-1 (mPGES-1), respectively, are key players in inflammation, and pharmacological suppression of these lipid mediators (LM) represents a strategy to intervene with inflammatory disorders. Previous studies revealed that the benzenesulfonamide scaffold displays efficient 5-LO-inhibitory properties. Here, we structurally optimized benzenesulfonamides which led to an N-phenyl-benzenesulfonamide derivative (compound 47) with potent inhibitory activities (IC50 = 2.3 and 0.4 mu M for isolated 5-LO and 5-LO in intact cells, respectively). Compound 47 prevented the interaction of 5-LO with its activating protein (FLAP) at the nuclear envelope in transfected HEK293 cells as shown by in situ proximity ligation assay. Comprehensive assessment of the LM profile produced by human macrophages revealed the ability of 47 to selectively down-regulate pro-inflammatory LMs (i.e. LTs and PGE(2)) in M1 but to enhance the formation of pro-resolving LMs (i.e. resolvins and maresins) in M2 macrophages. Moreover, 47 strongly inhibited LT formation and cell infiltration in two in vivo models of acute inflammation (i.e., peritonitis and air pouch sterile inflammation in mice). Together, 47 represents a novel LT biosynthesis inhibitor with an attractive pharmacological profile as anti-inflammatory drug that also promotes the biosynthesis of pro-resolving LM. (C) 2018 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2018.07.031
• 作为产物：
  描述：

  4-((4-Methyl-benzylidene)-amino)-benzoic acid ethyl ester 在 三乙酰氧基硼氢化钠 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 18.0h， 以2.48 g的产率得到ethyl 4-((4-methylbenzyl)amino)benzoate
  参考文献：
  名称：

  Discovery of a benzenesulfonamide-based dual inhibitor of microsomal prostaglandin E2 synthase-1 and 5-lipoxygenase that favorably modulates lipid mediator biosynthesis in inflammation

  摘要：

  Leukotrienes (LTs) and prostaglandin (PG)E-2, produced by 5-lipoxygenase (5-LO) and microsomal prostaglandin E-2 synthase-1 (mPGES-1), respectively, are key players in inflammation, and pharmacological suppression of these lipid mediators (LM) represents a strategy to intervene with inflammatory disorders. Previous studies revealed that the benzenesulfonamide scaffold displays efficient 5-LO-inhibitory properties. Here, we structurally optimized benzenesulfonamides which led to an N-phenyl-benzenesulfonamide derivative (compound 47) with potent inhibitory activities (IC50 = 2.3 and 0.4 mu M for isolated 5-LO and 5-LO in intact cells, respectively). Compound 47 prevented the interaction of 5-LO with its activating protein (FLAP) at the nuclear envelope in transfected HEK293 cells as shown by in situ proximity ligation assay. Comprehensive assessment of the LM profile produced by human macrophages revealed the ability of 47 to selectively down-regulate pro-inflammatory LMs (i.e. LTs and PGE(2)) in M1 but to enhance the formation of pro-resolving LMs (i.e. resolvins and maresins) in M2 macrophages. Moreover, 47 strongly inhibited LT formation and cell infiltration in two in vivo models of acute inflammation (i.e., peritonitis and air pouch sterile inflammation in mice). Together, 47 represents a novel LT biosynthesis inhibitor with an attractive pharmacological profile as anti-inflammatory drug that also promotes the biosynthesis of pro-resolving LM. (C) 2018 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2018.07.031

文献信息

• <i>O</i>-Phenylenediamine: a privileged pharmacophore of ferrostatins for radical-trapping reactivity in blocking ferroptosis
  作者：Xie-Huang Sheng、Cheng-Cheng Cui、Chao Shan、Yu-Zhen Li、Duo-Hong Sheng、Bin Sun、De-Zhan Chen

  DOI：10.1039/c8ob00546j

  日期：——

  magnitudes of amine conjugation and improves spin delocalization in the transition state. Additionally, a classical H-bond type interaction was discovered between a radical and an o-NH group as another transition state stabilizing effect. This type of radical-trapping mechanism is novel and has not been found in diphenylamine or traditional polyphenol antioxidants. It can be said that o-phenylenediamine is

  Ferroptosis是受调节的细胞死亡的一种非凋亡的铁依赖性形式，其特征是脂质过氧化氢的积累。由于它推测参与多种神经退行性疾病，因此引起了相当大的关注。Ferrostatins是最早被鉴定为肥大症的抑制剂，它们通过有效清除脂质双层中的自由基来抑制肥大症。然而，由于对脂质过氧自由基捕获机理的了解不足，其进一步的医学应用受到了限制。在这项研究中，进行了实验和理论方法来说明可能的铁过他汀脂质过氧化氢抑制机制。结果表明，邻位来自铁抑素的-胺（-NH）部分可同时与脂质自由基相互作用，然后在过渡态形成平面的七元环，并最终呈现出更高的反应性。NBO分析表明，形成的平面七元环迫使邻胺与芳族π系统更好地对准。它显着增加了胺共轭的幅度，并改善了过渡态下的自旋离域。另外，在自由基和邻-NH基团之间发现了经典的H键型相互作用，作为另一种过渡态稳定作用。这种类型的自由基捕获机制是新颖的，尚未在二苯胺或传统的多酚抗
• Alkyl formates as reagents for reductive amination of carbonyl compounds
  作者：Oleg I. Afanasyev、Ilia Cherkashchenko、Anton Kuznetsov、Fedor Kliuev、Sergey Semenov、Olga Chusova、Gleb Denisov、Denis Chusov

  DOI：10.1016/j.mencom.2020.01.037

  日期：2020.1

  Alkyl formates in the presence of basic additives can serve as a reagent in the direct reductive amination of carbonyl compounds. The developed procedure can be applied to various aldehydes and ketones with electron donating and electron withdrawing groups.

  在碱性添加剂存在下，烷基甲酸酯可以用作羰基化合物直接还原胺化反应的试剂。所开发的方法可以用于具有给电子和吸电子基团的各种醛和酮。
• 一种具有抗菌活性的苯佐卡因单取代衍生物的合成方法和应用
  申请人：河南师范大学

  公开号：CN109206333A

  公开（公告）日：2019-01-15

  本发明公开了一种具有抗菌活性的苯佐卡因单取代衍生物的制备方法，具体步骤为将一定量的苯佐卡因溶于N,N‑二甲基甲酰胺中，配置成溶液A；把一定量的溴代化合物和三乙胺溶于N,N‑二甲基甲酰胺中，配置成溶液B；把溶液A和溶液B以一定流速通过四氟泵送入一定反应温度的碳化硅反应器中，物料在微反应器中保持一定停留时间发生取代反应，收集反应后的物料，把得到的全部反应液倒入水中，用氯仿萃取反应液，合并有机相，浓缩后经硅胶柱层析分离(PE:EA＝5:1)得到单取代衍生物。本发明的合成工艺更加经济、环保、高效、便捷，且具有良好的抗菌作用。
• Reductive amination catalyzed by iridium complexes using carbon monoxide as a reducing agent
  作者：Alexey P. Moskovets、Dmitry L. Usanov、Oleg I. Afanasyev、Vasilii A. Fastovskiy、Alexander P. Molotkov、Karim M. Muratov、Gleb L. Denisov、Semen S. Zlotskii、Alexander F. Smol'yakov、Dmitry A. Loginov、Denis Chusov

  DOI：10.1039/c7ob01005b

  日期：——

  methodologies to provide access to amines represents a goal of fundamental importance. Herein we describe a systematic study for the construction of a variety of amines catalyzed by a well-defined homogeneous iridium complex using carbon monoxide as a reducing agent. The methodology was shown to be compatible with functional groups prone to reduction by hydrogen or complex hydrides.

  开发新颖，可持续的催化方法以提供与胺的接触代表了具有根本重要性的目标。本文中，我们描述了使用一氧化碳作为还原剂，通过定义明确的均相铱络合物催化的各种胺的构建的系统研究。结果表明，该方法与易于被氢或复杂氢化物还原的官能团兼容。
• Amination of Aryl Iodides Using a Fluorous-Tagged Ammonia Equivalent
  作者：Simon Dalsgaard Nielsen、Garrick Smith、Mikael Begtrup、Jesper Langgaard Kristensen

  DOI：10.1002/ejoc.201000367

  日期：2010.7

  A fluorous-tagged ammonia equivalent for the Cu-catalyzed amination of aryl iodides is described in which N-Boc-protected anilines are produced in high overall yield and purity. All purification steps are performed using Fluorous Solid-Phase Extraction (F-SPE) greatly simplifying and speeding up the isolation of the desired products.

  描述了用于芳基碘化物的 Cu 催化胺化的氟标记氨等价物，其中 N-Boc 保护的苯胺以高总产率和纯度生产。所有纯化步骤均使用氟固相萃取 (F-SPE) 进行，大大简化并加快了所需产物的分离。