bis[2-(4-methylphenylsulfonylamino)phenyl] diselenide

• 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: bis[2-(4-methylphenylsulfonylamino)phenyl] diselenide
• 英文别名: 4-methyl-N-[2-[[2-(p-tolylsulfonylamino)phenyl]diselanyl]phenyl]benzenesulfonamide；4-methyl-N-[2-[[2-[(4-methylphenyl)sulfonylamino]phenyl]diselanyl]phenyl]benzenesulfonamide
• 化学式: C₂₆H₂₄N₂O₄S₂Se₂
• 分子量: 650.54
• InChiKey: JMHGQKYPTKBXCO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.18
• 重原子数：
  36
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  109
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  茴香烯 、 bis[2-(4-methylphenylsulfonylamino)phenyl] diselenide 在 copper(II) bis(trifluoromethanesulfonate) 、 三乙胺 作用下， 以 氯仿 为溶剂， 反应 48.0h， 以58%的产率得到
  参考文献：
  名称：

  铜介导的一锅法将2-N-磺酰基-氨基芳基二硒化物转化为苯并[b] [1,4]硒代嗪

  摘要：

  建立了一个简单的程序，可以将2- N-甲苯磺酰基二硒化物一锅转化为苯并[ b ] [1,4]硒硒嗪。收集的数据表明，六元杂环是瞬态贫电子的邻亚氨基硒代醌（充当二烯）与富电子的烯烃（充当亲二烯体）的[4 + 2]环加成反应的结果。合成的关键步骤是在硒原子上的硒上进行1,4消除，从而导致杂二烯的生成，这需要催化量的三氟甲磺酸铜（II）才能激活硒-硒键。

  DOI：

  10.1002/adsc.201100587
• 作为产物：
  描述：

  双(2-硝基苯)二硒 在 吡啶 、 镍 、 一水合肼 作用下， 以 丙醇 为溶剂， 反应 27.0h， 生成 bis[2-(4-methylphenylsulfonylamino)phenyl] diselenide
  参考文献：
  名称：

  Functionalized alkyl and aryl diselenides as antimicrobial and antiviral agents: synthesis and properties

  摘要：

  The different dialkyl and diaryl diselenides with carbamoyl and sulfamoyl moieties 2, 3, 5 and other substituents in the ortho position of benzene ring 4, 7, 8 as well as derivatives of 1,2,4-benzoselenadiazine (6) were designed as antiviral and antimicrobial agents and synthesized. Some of them, particularly 8a and 8b, were found in the antiviral assay in vitro to be strong inhibitors of cytopathic activity encephalomyocarditis virus (EMCV). The compound 4a and 8a were found to have a broad spectrum of acivity against bacteria, yeasts and pathogenic fungi in vitro.

  DOI：

  10.1016/j.farmac.2003.08.003

文献信息

• A One-Pot Access to Benzo[b][1,4]selenazines from 2-Aminoaryl Diselenides
  作者：Stefano Menichetti、Antonella Capperucci、Damiano Tanini、Antonio L. Braga、Giancarlo V. Botteselle、Caterina Viglianisi

  DOI：10.1002/ejoc.201600351

  日期：2016.6

  Different 2-sulfonylaminoaryl diselenides substituted with electron-withdrawing or -donating groups are transformed in one pot into benzo[b][1,4]selenazines. The reaction uses a substoichiometric amount of Cu(OTf)2, and the mechanism involves a base-mediated 1,4-elimination at selenium with the generation of an o-iminoselenoquinone and a 2-sulfonylaminoselenolate anion. The former is a dienic species

  不同的被吸电子或给电子基团取代的 2-磺酰氨基芳基二硒化物在一锅中转化为苯并[b][1,4]硒嗪。该反应使用亚化学计量的 Cu(OTf)2，其机制涉及碱介导的 1,4-硒消除，同时生成 o-亚氨基硒代醌和 2-磺酰氨基硒代阴离子。前者是一种二烯类物质，可以与富电子亲二烯体反应生成目标环加合物。后者被空气氧化回起始的二硒化物，使其完全消耗。还描述了对选定硒嗪的 GPx 样活性的初步研究。
• Evaluation of selenide, diselenide and selenoheterocycle derivatives as carbonic anhydrase I, II, IV, VII and IX inhibitors
  作者：Andrea Angeli、Damiano Tanini、Caterina Viglianisi、Lucia Panzella、Antonella Capperucci、Stefano Menichetti、Claudiu T. Supuran

  DOI：10.1016/j.bmc.2017.03.013

  日期：2017.4

  A series of selenides, diselenides and organoselenoheterocycles were evaluated as carbonic anhydrase (CA, EC 4.2.1.1) inhibitors against the human (h) isoforms hCA I, II, IV, VII and IX, involved in a variety of diseases among which glaucoma, retinitis pigmentosa, epilepsy, arthritis and tumors etc. These investigated compounds showed inhibitory action against these isoforms and some of them were selective

  一系列硒化物，二硒化物和有机硒杂环化合物被评估为碳酸酐酶（CA，EC 4.2.1.1）抑制剂，可抵抗人类（h）亚型hCA I，II，IV，VII和IX，涉及多种疾病，其中青光眼，这些研究的化合物显示出对这些同工型的抑制作用，其中一些对膜结合同工型具有抑制胞质的选择性，因此使它们成为开发同工型选择性抑制剂的有趣线索。
• Copper‐Mediated One‐Pot Transformation of 2‐<i>N</i>‐Sulfonyl‐ aminoaryl Diselenides into Benzo[<i>b</i>][1,4]selenazines
  作者：Caterina Viglianisi、Lavinia Simone、Stefano Menichetti

  DOI：10.1002/adsc.201100587

  日期：2012.1

  for the one‐pot transformation of 2‐N‐tosylamino diselenides into benzo[b][1,4]selenazines has been established. The data collected indicate that the six‐membered heterocyclic ring is the result of a [4+2] cycloaddition reaction of a transient electron‐poor o‐iminoselenoquinone, acting as diene, with an electron‐rich alkene, performing as dienophile. The key step of the synthesis is a 1,4‐elimination

  建立了一个简单的程序，可以将2- N-甲苯磺酰基二硒化物一锅转化为苯并[ b ] [1,4]硒硒嗪。收集的数据表明，六元杂环是瞬态贫电子的邻亚氨基硒代醌（充当二烯）与富电子的烯烃（充当亲二烯体）的[4 + 2]环加成反应的结果。合成的关键步骤是在硒原子上的硒上进行1,4消除，从而导致杂二烯的生成，这需要催化量的三氟甲磺酸铜（II）才能激活硒-硒键。
• Functionalized alkyl and aryl diselenides as antimicrobial and antiviral agents: synthesis and properties
  作者：H Wójtowicz、M Chojnacka、J Młochowski、J Palus、L Syper、D Hudecova、M Uher、E Piasecki、M Rybka

  DOI：10.1016/j.farmac.2003.08.003

  日期：2003.12

  The different dialkyl and diaryl diselenides with carbamoyl and sulfamoyl moieties 2, 3, 5 and other substituents in the ortho position of benzene ring 4, 7, 8 as well as derivatives of 1,2,4-benzoselenadiazine (6) were designed as antiviral and antimicrobial agents and synthesized. Some of them, particularly 8a and 8b, were found in the antiviral assay in vitro to be strong inhibitors of cytopathic activity encephalomyocarditis virus (EMCV). The compound 4a and 8a were found to have a broad spectrum of acivity against bacteria, yeasts and pathogenic fungi in vitro.