4-methylbenzyl-4-nitrophenyl ether | 92200-00-5

• 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: 4-methylbenzyl-4-nitrophenyl ether
• 英文别名: (4-Nitro-phenyl)-(4-methyl-benzyl)-ether；1-Methyl-4-[(4-nitrophenoxy)methyl]benzene
• CAS: 92200-00-5
• 化学式: C₁₄H₁₃NO₃
• 分子量: 243.262
• InChiKey: UZSVWTIBVRMWID-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  55
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-methylbenzyl-4-nitrophenyl ether 在 甲酸 、 5%-palladium/activated carbon 、 氢气 、 溶剂黄146 作用下， 以 甲醇 、 乙醇 为溶剂， -3.0~20.0 ℃ 、500.01 kPa 条件下， 反应 0.5h， 生成 6-[(4-methylbenzyl)oxy]-1,3-benzothiazol-2-amine
  参考文献：
  名称：

  1,3-Benzothiazoles as Antimicrobial Agents

  摘要：

  Starting from 2-amino-1,3-mercaptobenzothiazoles recently reported (1a, 1b, 1c, 1d, 1e, 1f, 1g, 1h), a series of the corresponding 2-mercapto-1,3-benzothiazole isosters (2a, 2b, 2c, 2d, 2e, 2f, 2g, 2h) were screened for their in vitro antibacterial and antifungal activities. Results underline that the presence of the mercapto moiety at the 2-position of the heterocyclic nucleus is crucial for activity against bacteria. The biological screening against Candida spp. identified commercial 2f as the most promising compound as antifungal against Candida albicans and tropicalis. Molecular modeling studies supported these results. Then, to enlarge structure-activity relationship (SAR) studies on series 1, newly synthesized compounds (1k, 1l, 1m, 1n, 1o, 1p) were reported. All the compounds belonging to this series and bearing a bulky substituent at the 6-position of the aryl moiety showed high antifungal activity.

  DOI：

  10.1002/jhet.2222
• 作为产物：
  描述：

  4-甲基氯苄 、 4-nitrophenol sodium salt 生成 4-methylbenzyl-4-nitrophenyl ether
  参考文献：
  名称：

  脱甲基研究。IV。烷基-和芳基-对-硝基苯醚的体外和体内裂解。

  摘要：

  DOI：

  10.1021/jm00340a001

文献信息

• Discovery of anilino-furo[2,3- d ]pyrimidine derivatives as dual inhibitors of EGFR/HER2 tyrosine kinase and their anticancer activity
  作者：Monia Hossam、Deena S. Lasheen、Nasser S.M. Ismail、Ahmed Esmat、Ahmed M. Mansour、Abdel Nasser B. Singab、Khaled A.M. Abouzid

  DOI：10.1016/j.ejmech.2017.12.022

  日期：2018.1

  the focus of this study where a series of novel 4-anilino-furo[2,3-d]pyrimidine derivatives was designed, synthesized and biologically evaluated. Modification of the solvent accessible 5-position side chain greatly affected the in-vitro EGFR/HER2 inhibitory activity. Three derivatives bearing 5-carboxylic acid side chain, namely the 3-chloroanilino derivative (8c), the 3-bromoaniline (8d) and the lapatinib

  EGFR（表皮生长因子受体）和HER2（人类表皮生长因子受体2）负责多种癌症的发生，是本研究的重点，其中一系列新颖的4-苯胺基-呋喃[2,3- d ]设计，合成并进行了嘧啶衍生物的生物学评估。溶剂可及的5位侧链的修饰极大地影响了体外EGFR / HER2抑制活性。带有5-羧酸侧链的三个衍生物，即3-氯苯胺基衍生物（8c），3-溴苯胺（8d）和拉帕替尼类似物（10）表现出最显着的亚微摩尔EGFR抑制作用。令人惊讶的是，体外酯7h及其酸类似物10的分析显示结果分别对A549细胞系（IC 50 0.5和21.4μM）的抗增殖活性与EGFR抑制活性（18％和100％）之间存在显着差异，表明7h可能对做10的前药。体内结果也证实了这一假设，其中针对EAC（艾氏腹水癌）实体瘤模型的体内抗肿瘤评估显示7h和8d（10 mg / kg剂量）的抗肿瘤活性与吉非替尼在相同剂量下的抗肿瘤活性相当，分别具有67％
• Natural Product Neopeltolide as a Cytochrome <i>bc</i>₁ Complex Inhibitor: Mechanism of Action and Structural Modification
  作者：Xiao-Lei Zhu、Rui Zhang、Qiong-You Wu、Yong-Jun Song、Yu-Xia Wang、Jing-Fang Yang、Guang-Fu Yang

  DOI：10.1021/acs.jafc.8b06195

  日期：2019.3.13

  chemical structure of neopeltolide, leading to the synthesis of a series of new neopeltolide derivatives with much simpler chemical structures. The calculated binding energies (ΔGcal) of the newly synthesized analogues correlated very well (R2 = 0.90) with their experimental binding free energies (ΔGexp), which confirmed that the computational protocol was reliable. Compound 45, bearing a diphenyl ether

  从天然新科科动物的深水海绵标本中分离出海洋天然产物新科植物内酯。新pelolide已被证明是线粒体呼吸链中细胞色素bc 1复合物的新型抑制剂。然而，其详细的抑制机制仍是未知的。另外，由于新鸟苷内酯的化学结构非常复杂，因此很难合成。在当前的工作中，通过结合分子对接，分子动力学模拟和分子力学泊松-玻尔兹曼表面积计算，首次确定了新去内酯的结合模式，这表明新去内酯是bc 1的Q o抑制剂。复杂的。然后，根据抑制剂-蛋白质相互作用分析的指导，进行了结构修饰，目的在于简化新pelolide的化学结构，从而合成了一系列具有更简单化学结构的新neopeltolide衍生物。计算出的新合成类似物的结合能（ΔG cal）与它们的实验结合自由能（ΔG exp）具有很好的相关性（R 2 = 0.90 ），这证实了该计算方案是可靠的。具有二苯醚片段的化合物45已成功设计并合成为最有效的候选物（IC 50（＝ 12n
• Dual Nickel/Photoredox‐Catalyzed Synthesis of <i>N</i>‐formyl <i>N</i>,<i>N’</i>‐Diaryl Ethylenediamines via Multiple C−N/C−C Coupling of Nitroarenes with Trimethylamine
  作者：Tongtong Zheng、Zhe Feng、Jun‐An Ma、Chi Wai Cheung

  DOI：10.1002/adsc.202300431

  日期：2023.7.18

  motifs in medicinal chemistry. Whereas the C−N formation reactions based on anilines and aryl halides are the most direct methods to access N,N’-diaryl ethylenediamines, the photocatalytic synthetic version remains undeveloped. Herein we describe the dual nickel/photoredox-catalyzed amination reaction using nitroarenes and trimethylamine as reaction substrates. This cascade transformation hinges on the

  N , N'-二芳基乙二胺是有机合成中的常见原料，也是药物化学中的重要结构基序。虽然基于苯胺和芳基卤化物的 CN-N 形成反应是获得N , N'-二芳基乙二胺的最直接方法，但光催化合成方法仍未开发。在此，我们描述了使用硝基芳烃和三甲胺作为反应底物的双镍/光氧化还原催化的胺化反应。这种级联转化取决于分别基于硝基芳烃和三甲胺衍生的氮自由基和α-氨甲基自由基的多个CN和CC耦合事件。各种N-甲酰基N , N'-二芳基乙二胺可以根据该反应方案获得。随后的水解提供N , N'-二芳基乙二胺用于进一步衍生化。
• Demethylation Studies. IV. The in vitro and in vivo Cleavage of Alkyl- and Arylalkyl-p-nitrophenyl Ethers
  作者：Robert E. McMahon、Hilman W. Culp、Jack Mills、Frederick J. Marshall

  DOI：10.1021/jm00340a001

  日期：1963.7
• 1,3-Benzothiazoles as Antimicrobial Agents
  作者：Ivana Defrenza、Alessia Catalano、Alessia Carocci、Antonio Carrieri、Marilena Muraglia、Antonio Rosato、Filomena Corbo、Carlo Franchini

  DOI：10.1002/jhet.2222

  日期：2015.11

  Starting from 2-amino-1,3-mercaptobenzothiazoles recently reported (1a, 1b, 1c, 1d, 1e, 1f, 1g, 1h), a series of the corresponding 2-mercapto-1,3-benzothiazole isosters (2a, 2b, 2c, 2d, 2e, 2f, 2g, 2h) were screened for their in vitro antibacterial and antifungal activities. Results underline that the presence of the mercapto moiety at the 2-position of the heterocyclic nucleus is crucial for activity against bacteria. The biological screening against Candida spp. identified commercial 2f as the most promising compound as antifungal against Candida albicans and tropicalis. Molecular modeling studies supported these results. Then, to enlarge structure-activity relationship (SAR) studies on series 1, newly synthesized compounds (1k, 1l, 1m, 1n, 1o, 1p) were reported. All the compounds belonging to this series and bearing a bulky substituent at the 6-position of the aryl moiety showed high antifungal activity.