2,2'-disulphanediylbis(N-(pyridin-2-ylmethylene)aniline) | 40946-29-0

• 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: 2,2'-disulphanediylbis(N-(pyridin-2-ylmethylene)aniline)
• 英文别名: o,o′-(N,N′-dipicolinyldene)diazadiphenyl disulfide；2,2'-di(pyridyl-2-methyleneimine)diphenyl disulfide；o,o'-(N,N'-dipicolinylidene)diazadiphenyl disulfide；2,2′-di(pyridyl-2-methyleneimine)diphenyl disulfide；α,α'--di-2-picolin；N,N'-bis-pyridin-2-ylmethylene-2,2'-disulfanediyl-bis-aniline；N,N'-(disulfanediylbis(2,1-phenylene))bis(1-(pyridin-2-yl)methanimine)；bis{2-[(pyridin-2-ylmethylidene)amino]phenyl} disulfide；2,2'-dithiobis[N-(pyridin-2-ylmethylene)aniline]；1-pyridin-2-yl-N-[2-[[2-(pyridin-2-ylmethylideneamino)phenyl]disulfanyl]phenyl]methanimine
• CAS: 40946-29-0
• 化学式: C₂₄H₁₈N₄S₂
• 分子量: 426.566
• InChiKey: GYLATGKIEKPBSU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  101
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  双(乙腈)氯化钯(II) 、 2,2'-disulphanediylbis(N-(pyridin-2-ylmethylene)aniline) 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 以65%的产率得到[Pd(L)Cl]
  参考文献：
  名称：

  含有席夫碱配体的单核和四核钯 (II) 配合物的晶体结构、抗菌、抗氧化剂和核酸相互作用

  摘要：

  摘要 两种新的钯配合物 [Pd(dpbs)Cl] (1) 和 [Pd4(dbbs)4] (2)（其中 (dpbs)2 = o,o'-(N,N'-二吡啶甲基）二氮杂二苯基二硫化物和(dbbs)2 = N,N'-(1,1'-dithio-bis(phenylene))-bis(salicylideneimine))，已通过分析和光谱（电子、红外、1H、13C 光谱）技术合成和表征. 1 和 2 的结构已通过单晶 X 射线衍射实验得到解决，这表明 O、N 和 S 供体在钯 (II) 周围存在扭曲的方形平面配位几何结构。已经筛选了金属螯合物的抗菌和抗氧化活性，并与它们各自的配体进行了比较。已经通过电子吸收、发射光谱和粘度测量研究了复合物的结合特性。已经研究了溴化乙锭的竞争性荧光研究以及碘化物浓度对复合 DNA 系统荧光的影响。所有这些实验结果表明钯复合物与 DNA 结合，可能是通过凹槽结合。热力学参数、焓变

  DOI：

  10.1080/00958972.2016.1208818
• 作为产物：
  描述：

  2-氨基苯硫醇 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 12.0h， 生成 2,2'-disulphanediylbis(N-(pyridin-2-ylmethylene)aniline)
  参考文献：
  名称：

  使用有机-无机杂化纳米粒子对水性介质中的碘化物进行纳摩尔检测：在尿液分析中的应用。

  摘要：

  已合成并表征了亚胺联吡啶偶联（ILPC）受体。通过结合实验和理论研究了这些受体的吸收和荧光特性。将ILPC受体加工成有机纳米颗粒（ONP），然后用金纳米颗粒（AuNPs）修饰，以选择性识别碘。选择性识别行为通过荧光光谱的变化，低检测限（1.4 nM）和在水性体系中无干扰来验证。本研究代表了使用有机-无机杂化纳米颗粒（ONPs-AuNPs）在水性介质中纳摩尔检测碘化物的第一个实例。该探头已成功用于尿液样品中碘含量的检测。

  DOI：

  10.1002/cplu.201402312
• 作为试剂：
  描述：

  sodium hydroxide 、 zinc(II) perchlorate 在 2,2'-disulphanediylbis(N-(pyridin-2-ylmethylene)aniline) 作用下， 反应 8.0h， 生成 zinc(II) oxide
  参考文献：
  名称：

  在无溶剂条件下合成苯并噻唑，苯并咪唑和苯并恶唑衍生物的球磨策略

  摘要：

  通过球磨策略，使用可回收的ZnO-NP ，开发了一种方便的无溶剂合成苯并噻唑，苯并咪唑和苯并恶唑衍生物的方法。该方法提供了对环境友好的反应条件，该条件在生态规模上得分很高，而E因子却很低。该过程即使在几克规模的情况下也非常高效，并且可以轻松实现产品隔离。

  DOI：

  10.1039/c4gc01142b

文献信息

• Bovine serum albumin triggered waste-free aerobic oxidative coupling of thiols into disulphides on water: An extended synthesis of bioactive dithiobis(phenylene)bis(benzylideneimine) via sequential oxidative coupling–condensation reactions in one pot from aminothiophenol and benzaldehyde
  作者：Saima、Aditya G. Lavekar、Rajesh Kumar、Arun K. Sinha

  DOI：10.1016/j.molcatb.2015.03.008

  日期：2015.6

  formation of disulphides (SS) without using any metal/non-metal complexes, bases and additives, which renders the process environmentally benign and economically attractive with good recyclability (up to four cycles). The developed green protocol was further extended for synthesis of diallyldisulphide (DADS), an important constituent of natural occurring allicin. Among various synthesized disulphides, bis

  牛血清白蛋白（BSA）已被研究用于“水”上硫醇（芳香族，杂环以及脂肪族）的有氧氧化偶联形成二硫化物（SS）的形成，而无需使用任何金属/非金属配合物，碱和添加剂。使该工艺在环境上无害且在经济上具有吸引力，并具有良好的可回收性（最多四个循环）。已开发的绿色方案进一步扩展为合成二烯丙基二硫化物（DADS），这是天然存在的大蒜素的重要组成部分。在各种合成的二硫化物中，通过2-氨基硫酚在BSA中的氧化偶合获得的双（2-氨基苯基）二硫化物在同一罐中进一步用于与苯甲醛的缩合反应，因此易于获得具有生物活性的二硫代双（亚苯基）双（苄基亚胺）。
• Nickel(II)‐Mediated Reversible Thiolate/Disulfide Conversion as a Mimic for a Key Step of the Catalytic Cycle of Methyl‐Coenzyme M Reductase
  作者：Anirban Bhandari、Saikat Mishra、Ram Chandra Maji、Akhilesh Kumar、Marilyn M. Olmstead、Apurba K. Patra

  DOI：10.1002/anie.202001363

  日期：2020.6.2

  methanotrophic microbes. Model complexes that illustrate Ni-ion mediated reversible thiolate/disulfide transformation are unknown. In this paper we report the synthesis, crystal structure, spectroscopic properties and redox interconversions of a set of NiII complexes comprising a tridentate N2 S donor thiol and its analogous N4 S2 donor disulfide ligands. These complexes demonstrate reversible NiII -thiolate/NiII

  根据公认的机制，甲基辅酶M还原酶（MCR）涉及Ni介导的硫醇盐到二硫化物的转化，从而在甲烷营养化微生物的节能途径中维持甲烷形成的催化循环。说明Ni离子介导的可逆硫醇盐/二硫键转化的模型配合物是未知的。在本文中，我们报告了一组NiII配合物的合成，晶体结构，光谱性质和氧化还原互变，该配合物包括三齿N2 S供体硫醇及其类似的N4 S2供体二硫配体。这些配合物通过巯基和二硫化物单自由基阴离子显示出可逆的NiII-硫醇盐/ NiII-二硫化物（结合和未结合的二硫化物-S到NiII）转变，类似于MCR催化循环的第一步。
• Dhillon, Harmeet; Singh, Urvasini; Pooja, Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical and Analytical, 2008, vol. 47, # 10, p. 1508 - 1511
  作者：Dhillon, Harmeet、Singh, Urvasini、Pooja、Kumbhat, Sunita

  DOI：——

  日期：——
• Spectroscopic differences between heterocyclic benzothiazoline, -thiazole and imine containing ligands and comparison of the Co and Cu pyridine benzothiazole and imine complexes
  作者：Lauren J. Carlson、Jenna Welby、Kelly A. Zebrowski、Matthew M. Wilk、Rachel Giroux、Nicole Ciancio、Joseph M. Tanski、Amy Bradley、Laurie A. Tyler

  DOI：10.1016/j.ica.2010.09.002

  日期：2011.1

  Five heterocyclic benzothiazoline and -thiazole analogs have been synthesized and characterized by H-1 NMR and IR spectroscopy. The analogs fall into two different classes, (a) those which contain one benzothiazoline group adjacent to the heterocyclic ring system (starting with 2-pyridinecarboxaldehyde, 2-thiophenecarboxaldehyde or 2-furaldehyde), and (b) those which have two benzothiazoline substituents (starting with 2,6-pyridinecarboxaldehyde and 2,5-thiohenecarboxaldehyde). In addition, the imine containing ligands, bis-2-[(pyridin-2-ylmethylene)-imino]-benzenethiol disulfide (PyIS)(2) and bis-2-[(thiophen-2-ylmethylene)-imino]-benzenethiol disulfide(ThIS)(2), were prepared starting with the disulfide of 2-aminothiophenol. Each species has been characterized by H-1 NMR and IR spectroscopies. Ligation reactions with 2-(2-pyridyl) benzothiazoline (Py(Bt)) and Cu(OAc)(2)center dot 1H(2)O resulted in the formation of a dinuclear species containing two copper ions, two ligand frames and two acetate groups, [Cu(PyA-S)( OAc)](2) (1). Both copper ions are five-coordinate and bonded to one monodentate acetate, one ligand frame (NNS) and one bridging thiolate. Ligation reaction with 2-(2-pyridyl) benzothiazole (Py(oBt)) and CoCl2 center dot xH(2)O or Cu(BF4)(2)center dot xH(2)O resulted in the formation of a six-coordinate, octahedral Co(II) complex, cis-[Co(Py(oBt)(2)Cl-2] (2) and a five coordinate Cu(II) complex, [Cu(Py(oBt))(2)(OH2)](BF4) (3), respectively. All complexes have been characterized by X-ray crystallography as well as UV-Vis and IR spectroscopy. (C) 2010 Elsevier B.V. All rights reserved.
• Spectroscopic, electrochemical and DNA binding studies of some monomeric copper(II) complexes containing N2S(thiolate)Cu core and N4S(disulfide)Cu core
  作者：Manjuri K. Koley、Om Prakash Chouhan、Sumit Biswas、Joseph Fernandes、Arnab Banerjee、Anjan Chattopadhyay、Babu Varghese、Periakaruppan T. Manoharan、Aditya P. Koley

  DOI：10.1016/j.ica.2016.10.045

  日期：2017.2

  We report the synthesis, characterization and spectroscopic results of the Cu(II) complexes [Cu(pabt) (OH2)](ClO4) (1), [Cu(pabt)(Imz)](ClO4) (2), [Cu(Pabt)(N-Melmz)](ClO4) (3), [Cu(pabt)Cl] (4), [Cu(pma) Cl] (5), [Cu(pdta)Cl]Cl (6) and [Cu(reduced-pdta)Cl]Cl (7), (Hpabt = N-(2-mercaptophenyl)-2'-pyridyl-methylenimine, Hpma = N-(2-pyridylmethyl)-2-mercaptoaniline, pdta = 2,2'-di(pyridyl-2-methyleneimine)diphenyl disulfide, reduced-pdta = 2,2'-di(pyridyl-2-methylamine)diphenyl disulfide, Imz = imidazole, N-MeImz = N-methylimidazole). Electronic spectra of all these compounds display strong LMCT bands in the visible region mainly associated with S -> Cu(II), and consistent with TDDFT results. A four-line EPR pattern originating from the interaction of the unpaired electron with the central Cu-63/65 nucleus (I = 3/2, natural abundances: Cu-63, 69.17%; Cu-65, 30.83%) with the isotropic coupling constant (A(iso)) values of 80 +/- 1.5 G at RT for all these complexes suggests monomeric nature in solution. The redox behavior of these compounds show either nearly reversible or quasi-reversible Cu(II)/Cu(I) couple with redox potentials within the range -0.08 to -0.20 V versus Ag/AgCl. Some of these compounds show strong intercalative DNA binding and its complete cleavage. 1-3 exhibit remarkable cytotoxicity against C6 glioma cell line and human cervical cancer HeLa cell line. IC50 values of 2 and 3 for the cervical cancer HeLa cell line reveal that they exhibit higher cytotoxicity than many reported Cu(II) compounds. (C) 2016 Elsevier B.V. All rights reserved.