(4-methylsulfonylbenzylidene)phenylamine | 1239645-71-6

• 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-methylsulfonylbenzylidene)phenylamine
• 英文别名: N-(4-(methylsulfonyl)benzylidene)aniline；(E)-N-[4-(Methylsulfonyl)benzylidene]aniline；1-(4-methylsulfonylphenyl)-N-phenylmethanimine
• CAS: 1239645-71-6
• 化学式: C₁₄H₁₃NO₂S
• 分子量: 259.329
• InChiKey: ZMACKELRUXDPGN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  54.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  靛红酸酐 、 (4-methylsulfonylbenzylidene)phenylamine 以 neat (no solvent, gas phase) 为溶剂， 以81%的产率得到2-(4-methylsulfonylphenyl)-3-phenyl-1,3-benzdiazinan-4-one
  参考文献：
  名称：

  Analogue-based design, synthesis and docking of non-steroidal anti-inflammatory agents. Part 2: Methyl sulfanyl/methyl sulfonyl substituted 2,3-diaryl-2,3-dihydro-1H-quinazolin-4-ones

  摘要：

  A series of methyl sulfanyl/methyl sufonyl substituted 2,3-diaryl-2,3-dihydro-1H-quinazolin-4-one were designed using analogue-based design, scaffold hopping and shape similarity matching. The designed compounds were synthesized in 2-3 steps with simple chemistry and screened by ovine cyclooxygenases (COXs) inhibitory assay and carrageenan-induced rat paw edema assay. Among the screened compounds, two compounds exhibited 100% cyclooxygenase-2 (COX-2) inhibitory potency without showing cycloxygenase-1 (COX-1) inhibition at 20 mu M. The compounds also showed promising in vivo anti-inflammatory potential. A structure-activity relationship within the dataset was established by correlating the effect of aromatic ring substituent constants, structural variables and physico-chemical descriptors with in vivo anti-inflammatory activity. Molecular docking studies were also performed on the title compounds to study the binding interactions to COX-2 active site residues. The experimentally determined COX-2 inhibitory activity was found moderately correlating with binding modes predicted for compounds by Glide XP dock scoring function. The 2,3-diaryl-2,3-dihydro-1H-quinazolin-4-one pharmacophore reported herein should be a new lead for further development of novel non-steroidal anti-inflammatory agents. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.09.069
• 作为产物：
  描述：

  苯胺 在 potassium peroxymonosulfate 、 溶剂黄146 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 水 为溶剂， 反应 10.0h， 生成 (4-methylsulfonylbenzylidene)phenylamine
  参考文献：
  名称：

  Analogue-based design, synthesis and docking of non-steroidal anti-inflammatory agents. Part 2: Methyl sulfanyl/methyl sulfonyl substituted 2,3-diaryl-2,3-dihydro-1H-quinazolin-4-ones

  摘要：

  A series of methyl sulfanyl/methyl sufonyl substituted 2,3-diaryl-2,3-dihydro-1H-quinazolin-4-one were designed using analogue-based design, scaffold hopping and shape similarity matching. The designed compounds were synthesized in 2-3 steps with simple chemistry and screened by ovine cyclooxygenases (COXs) inhibitory assay and carrageenan-induced rat paw edema assay. Among the screened compounds, two compounds exhibited 100% cyclooxygenase-2 (COX-2) inhibitory potency without showing cycloxygenase-1 (COX-1) inhibition at 20 mu M. The compounds also showed promising in vivo anti-inflammatory potential. A structure-activity relationship within the dataset was established by correlating the effect of aromatic ring substituent constants, structural variables and physico-chemical descriptors with in vivo anti-inflammatory activity. Molecular docking studies were also performed on the title compounds to study the binding interactions to COX-2 active site residues. The experimentally determined COX-2 inhibitory activity was found moderately correlating with binding modes predicted for compounds by Glide XP dock scoring function. The 2,3-diaryl-2,3-dihydro-1H-quinazolin-4-one pharmacophore reported herein should be a new lead for further development of novel non-steroidal anti-inflammatory agents. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.09.069

文献信息

• Fe₃O₄/PEG-SO₃H as a heterogeneous and magnetically-recyclable nanocatalyst for the oxidation of sulfides to sulfones or sulfoxides
  作者：Saeideh Mirfakhraei、Malak Hekmati、Fereshteh Hosseini Eshbala、Hojat Veisi

  DOI：10.1039/c7nj02513k

  日期：——

  glycol-coated Fe3O4 nanocomposite (Fe3O4/PEG-SO3H) as a greatly effective and ecological nanocatalyst for the selective oxidation of sulfides to sulfoxides or sulfones with brilliant yields under solvent-free conditions by employing 30% hydrogen peroxide as the oxidant. A number of sulfides containing alcohol, ester, and aldehyde functional groups were fruitfully and selectively oxidized without altering the desired

  我们在下面介绍一种磺化-聚乙二醇涂层的Fe 3 O 4纳米复合材料（Fe 3 O 4 / PEG-SO 3 H），它是一种非常有效的生态纳米催化剂，用于在溶剂中将硫化物选择性氧化为亚砜或砜，并具有出色的收率。游离条件，采用30％的过氧化氢作为氧化剂。在不改变所需特性的情况下，许多含有醇，酯和醛官能团的硫化物被有效地和选择性地氧化。磁性纳米催化剂（Fe 3 O 4 / PEG-SO 3H）可以通过使用外部磁性工具方便快捷地回收，并循环使用10多次以上，而不会显着降低其催化性能。
• Design, synthesis, and biological evaluation of new 1,4‐diarylazetidin‐2‐one derivatives (β‐lactams) as selective cyclooxygenase‐2 inhibitors
  作者：Hadi Arefi、Nima Naderi、Amir B. Irani Shemirani、Mina Kiani Falavarjani、Mahsa Azami Movahed、Afshin Zarghi

  DOI：10.1002/ardp.201900293

  日期：2020.3

  A new series of 1,4‐diarylazetidin‐2‐one derivatives (β‐lactams) were designed and synthesized to evaluate their biological activities as selective cyclooxygenase‐2 (COX‐2) inhibitors. In vitro COX‐1 and COX‐2 inhibition studies showed that all compounds were selective inhibitors of the COX‐2 isozyme with IC50 values in the 0.05–0.11 µM range, and COX‐2 selectivity indexes in the range of 170–703.7

  设计并合成了一系列新的 1,4-二芳基氮杂环丁烷-2-one 衍生物（β-内酰胺类），以评估其作为选择性环氧合酶-2（COX-2）抑制剂的生物活性。体外 COX-1 和 COX-2 抑制研究表明，所有化合物都是 COX-2 同工酶的选择性抑制剂，IC50 值在 0.05-0.11 µM 范围内，COX-2 选择性指数在 170-703.7 范围内。在合成的β-内酰胺类中，3-甲氧基-4-(4-(甲基磺酰基)苯基)-1-(3,4,5-三甲氧基苯基)氮杂环丁烷-2-酮(4j)在N-1苯基上具有三甲氧基环表现出最高的 COX-2 抑制选择性和效力，甚至比参考药物塞来昔布更有效。还使用福尔马林试验测定合成化合物的镇痛活性。化合物4f在合成的分子中表现出最好的镇痛活性。分子模型研究表明，甲基磺酰基药效团可以插入到 COX-2 活性位点的二级口袋中，与 Arg513 相互作用。获得的结构-活性数据表明
• Synthesis of Polysubstituted Pyrroles via Silver-Catalyzed Oxidative Radical Addition of Cyclopropanols to Imines
  作者：Yulu Zhou、Mingchang Wu、Yi Liu、Cungui Cheng、Gangguo Zhu

  DOI：10.1021/acs.orglett.0c02735

  日期：2020.10.2

  two-atom subunit, is developed. The reaction takes place under mild conditions and produces a broad array of polysubstituted pyrroles in medium to high yields. It represents the first example of oxidative radical addition to imines, thus offering a new choice for the direct C–H functionalization of imines.

  开发了一种银催化的正式[3 + 2]环加成反应，其中环丙醇为C3亚基，亚胺为两个原子亚基。该反应在温和的条件下进行，并以中等至高产率产生各种各样的多取代的吡咯。它代表了亚胺氧化自由基加成的第一个例子，从而为亚胺直接CHH功能化提供了新的选择。
• Selective hydrogen peroxide oxidation of sulfides to sulfones with carboxylated multi-walled carbon nano tubes (MWCNTs-COOH) as heterogeneous and recyclable nanocatalysts under organic solvent-free conditions
  作者：Hojat Veisi、Fereshteh Hosseini Eshbala、Saba Hemmati、Mehdi Baghayeri

  DOI：10.1039/c4ra14964e

  日期：——

  This study deals with oxidation of sulfides to sulfones by using a heterogeneous and recyclable nanocatalyst.

  这项研究涉及使用一种异质且可回收的纳米催化剂将硫化物氧化为砜。
• A molybdenum based metallomicellar catalyst for controlled and selective sulfoxidation reactions in aqueous medium
  作者：Rajan Deepan Chakravarthy、Venkatachalam Ramkumar、Dillip Kumar Chand

  DOI：10.1039/c3gc42245c

  日期：——

  A surfactant based molybdenum system that exhibits catalytic activity for sulfoxidation reactions of various organic sulfides in aqueous medium has been developed and comprehensively characterized using IR, XRD, NMR, ESI-MS, DLS and TEM. The catalyst showcases remarkable selectivity for the preparation of both sulfoxides and sulfones in the range of good to excellent yields. Furthermore, the catalyst showed a high degree of tolerance towards various sensitive functional groups such as hydroxyl, acetal, aldehyde, amine, imine, oxime, cyano and alkene.

  一种基于表面活性剂的钼系统被开发出来，展现了在水介质中对各种有机硫化物的硫氧化反应的催化活性，并通过红外光谱（IR）、X射线衍射（XRD）、核磁共振（NMR）、电喷雾质谱（ESI-MS）、动态光散射（DLS）和透射电子显微镜（TEM）进行了全面表征。该催化剂在制备硫氧化物和硫酮方面表现出显著的选择性，产率范围从良好到优秀。此外，该催化剂对多种敏感官能团（如羟基、醛、亚胺、腈和烯烃）表现出较高的耐受性。