bis{2-[(thiophen-2-ylmethylidene)amino]phenyl} disulfide

• 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-[(thiophen-2-ylmethylidene)amino]phenyl} disulfide
• 英文别名: 1-thiophen-2-yl-N-[2-[[2-(thiophen-2-ylmethylideneamino)phenyl]disulfanyl]phenyl]methanimine
• 化学式: C₂₂H₁₆N₂S₄
• 分子量: 436.646
• InChiKey: KVGIZQJTLOIAHX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  28
• 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：
  132
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  bis{2-[(thiophen-2-ylmethylidene)amino]phenyl} disulfide 在 三氢化钐 、 四氯化钛 作用下， 以 四氢呋喃 为溶剂， 反应 0.17h， 以52%的产率得到2-(2-噻吩基)苯并噻唑
  参考文献：
  名称：

  低价钛试剂高效合成2-芳基苯并噻唑衍生物

  摘要：

  通过由 TiCl4/Sm 系统促进的双-（2-苯甲氨基苯基）二硫化物的新型还原环化，以良好的收率完成了 2-芳基苯并噻唑衍生物的新型且简便的合成。这种新方法的优点是原料容易获得，反应时间短，收率中等至良好。

  DOI：

  10.1080/00397910903227230
• 作为产物：
  描述：

  2-氨基苯硫醇 在 碘酸 作用下， 以 乙醇 为溶剂， 反应 0.5h， 生成 bis{2-[(thiophen-2-ylmethylidene)amino]phenyl} disulfide
  参考文献：
  名称：

  Synthesis and characterization of N,N′-bis(2-thenylidene)-2,2′-diaminodiphenyl disulfideag

  摘要：

  DOI：

  10.1016/s0031-6865(97)00034-4

文献信息

• DNA-BSA interaction, cytotoxicity and molecular docking of mononuclear zinc complexes with reductively cleaved N2S2 Schiff base ligands
  作者：Saeedeh Asadizadeh、Mehdi Amirnasr、Farzaneh Fadaei Tirani、Alireza Mansouri、Kurt Schenk

  DOI：10.1016/j.ica.2018.08.037

  日期：2018.11

  The synthesis of three potentially tetradentate, N2S2 Schiff-base-ligands, containing a disulfide bond, (LSSLThio)-S-Thio(L1), (LSSLBr)-S-Br(L2) and (LSSLDiMeO)-S-DiMeO (L3) are reported. These ligands undergo reductive disulfide bond scission upon reaction with PPh3 in the presence of Zn2+ ion. [(LS)-S-DiOMe](-), [(LS)-S-Thio](-) and [(LS)-S-Br](-) are the resulting bidentate thiolate-imine anions respectively, which upon reaction with Zn2+ produce three new zinc (II) complexes: [Zn((LSN)-S-Thio)(2)] (1), [Zn((LSN)-S-Br)(2)] (2) and [Zn((LSN)-S-DiOMe)(2)] (3). The structures of (L1) and 1-3 complexes were determined by X-ray diffraction. The interaction of 1-3 with CT-DNA have been investigated by absorption, emission, and CD spectroscopic methods and thermal denaturation measurements. The resulting data reveal that 1-3 show effective binding to CT-DNA (K-b = 2.2 x 10(4) to 1 x 10(5) L mol(-1)). The binding mode of DNA with 1-3 has also been investigated by molecular docking. The protein binding ability of 1-3 has been tested by monitoring the tryptophan emission intensity using BSA as a model protein. The quenching mechanism of BSA by the zinc complexes is static (k(q) = 1.66 to 3.4 x 10(13) L-1 mol s(-1)). It is remarkable that 1-3 exhibit effective cytotoxicity against two human tumour cell lines (HeLa and MCF-7). The potent cytotoxic effects of 2 and 3, with IC50 values of 19.93 and 20.11 respectively, are higher relative to clinically used cisplatin (IC50 = 23.50) against the MCF-7 cell line, indicating that 2 and 3 may have the potential to act as effective metal-based anticancer drugs.
• 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.
• Efficient Synthesis of 2-Arylbenzothiazole Derivatives with the Aid of a Low-Valent Titanium Reagent
  作者：Da-Qing Shi、Shao-Feng Rong、Guo-Lan Dou

  DOI：10.1080/00397910903227230

  日期：2010.7.12

  A novel and facile synthesis of 2-arylbenzothiazole derivatives was accomplished in good yields via the novel reductive cyclization of bis-(2-benzalaminophenyl)disulfide promoted by the TiCl4/Sm system. The advantages of this new method are the easily accessible starting materials, short reaction time, and moderate to good yields.

  通过由 TiCl4/Sm 系统促进的双-（2-苯甲氨基苯基）二硫化物的新型还原环化，以良好的收率完成了 2-芳基苯并噻唑衍生物的新型且简便的合成。这种新方法的优点是原料容易获得，反应时间短，收率中等至良好。
• Synthesis and characterization of N,N′-bis(2-thenylidene)-2,2′-diaminodiphenyl disulfideag
  作者：Semra Ĭde、Nilgün Ancin、Selma Gül Öztas、Mürşide Tüzün

  DOI：10.1016/s0031-6865(97)00034-4

  日期：1998.1