4-Chloro-5-<(4-nitrophenyl)imino>-5H-1,2,3-dithiazole

• 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-Chloro-5-<(4-nitrophenyl)imino>-5H-1,2,3-dithiazole
• 英文别名: 4-Chloro-5-<(p-nitrophenyl)imino>-5H-1,2,3-dithiazole；N-(4-chloro-5H-1,2,3-dithiazol-5-ylidene)-4-nitroaniline；5-(4-nitrophenyl)-4-chloro-5H-1,2,3-dithiazole；5-(p-nitrophenylimino)-4-chloro-1,2,3-dithiazole；4-Chloro-5-[(p-nitrophenyl)imino]-5H-1,2,3-dithiazole
• 化学式: C₈H₄ClN₃O₂S₂
• 分子量: 273.724
• InChiKey: NNWSLHUVQSYOBD-NTMALXAHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.0
• 重原子数：
  16.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  68.39
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  4-Chloro-5-<(4-nitrophenyl)imino>-5H-1,2,3-dithiazole 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 以90%的产率得到异硫代氰基4-硝基苯酯
  参考文献：
  名称：

  Besson, Thierry; Rees, Charles W., Journal of the Chemical Society. Perkin transactions I, 1995, # 13, p. 1659 - 1662

  摘要：

  DOI：
• 作为产物：
  描述：

  4-硝基苯胺 、 4,5-二氯-1,2,3-二噻唑氯化物 以 二氯甲烷 为溶剂， 反应 10.0h， 以70%的产率得到4-Chloro-5-<(4-nitrophenyl)imino>-5H-1,2,3-dithiazole
  参考文献：
  名称：

  新型6-取代的苯并噻唑-2-基吲哚[1,2- c ]喹唑啉和苯并咪唑并[1,2- c ]喹唑啉

  摘要：

  描述了合成吲哚[1,2- c ]喹唑啉（8）和苯并咪唑并[1,2- c ]喹唑啉（9）的合成途径和初步生物学评价。通过适当的二胺（例如2-（2-氨基苯基）吲哚或2-（2-氨基苯基）苯并咪唑）与2-氰基苯并噻唑的缩合获得产物。这项工作进一步证明了微波的普遍适用性，可以轻松快速地获得具有潜在药物价值的原始杂环。

  DOI：

  10.1016/s0040-4020(02)01593-4

文献信息

• Reactions of 5-arylimino-4-chloro-5H-1,2,3-dithiazoles with stable phosphoranes: Novel preparation of dithiomethylenephosphoranes
  作者：Hyi-Seung Lee、Kyongtae Kim

  DOI：10.1016/0040-4039(95)02286-4

  日期：1996.2

  reactions of 5-arylimino-4-chloro-5H-1,2,3-dithiazoles with 2 equivalents of stable phosphoranes such as carboethoxymethylene-, acetylmethylene-, 4-chlorobenzoylmethylene-, and cyanomethylenetriphenylphosphoranes in the presence of pyridine in CH2Cl2 at room temperature gave a new type of the corresponding phosphoranes with aryliminocyanomethyldithiomethylene moiety as a major product.

  5-吡啶基-4-氯-5H-1,2,3-二噻唑与2当量的稳定phosphor烷在CH 2 Cl中在吡啶存在下的反应，如碳乙氧基亚甲基，乙酰基亚甲基，4-氯苯甲酰基亚甲基和氰基亚甲基三苯基膦2在室温下得到一种新型的相应的正膦，其主要成分是芳基氨基氰基甲基二硫亚甲基。
• Novel synthesis of 1-aryl-3-chloro-3-phenylazetidin-2-one-4-spiro-5′-4′-chloro-5′H-1′,2′,3′-dithiazoles and bis(2-oxo-azetidin-4-yl) trisulfides
  作者：Moon-Kook Jeon、Kyongtae Kim、Yung Ja Park

  DOI：10.1039/b103974c

  日期：——

  Treatment of 5-arylimino-4-chloro-5H-1,2,3-dithiazoles with in situ generated (chloro)phenylketene in CH2Cl2 at rt gave azetidin-2-one-4-spiro-5′-(1′,2′,3′-dithiazoles) as major products, which reacted with primary and secondary alkylamines in CH2Cl2 at rt to afford bis(2-oxo-azetidin-4-yl) trisulfides in good to excellent yields.

  将 5-芳基亚氨基-4-氯-5H-1,2,3-二噻唑与原位生成的（氯）苯基乙烯在 CH2Cl2 中于恒温条件下进行处理，得到的主要产物是氮杂环丁烷-2-酮-4-螺-5â²-（1â²,2â²,3â²-二噻唑），这些产物与伯、仲烷基胺在 中于恒温条件下进行反应，得到双（2-氧代氮杂环丁烷-4-基）三硫化物，收率良好至极佳。
• Synthesis and evaluation of 1,2,3-dithiazole inhibitors of the nucleocapsid protein of feline immunodeficiency virus (FIV) as a model for HIV infection
  作者：Tuomo Laitinen、Theres Meili、Maria Koyioni、Panayiotis A. Koutentis、Antti Poso、Regina Hofmann-Lehmann、Christopher R.M. Asquith

  DOI：10.1016/j.bmc.2022.116834

  日期：2022.8

  We disclose a series of potent anti-viral 1,2,3-dithiazoles, accessed through a succinct synthetic approach from 4,5-dichloro-1,2,3-dithiazolium chloride (Appel’s salt). A series of small libraries of compounds were screened against feline immunodeficiency virus (FIV) infected cells as a model for HIV. This approach highlighted new structure activity relationship understanding and led to the development

  我们公开了一系列有效的抗病毒 1,2,3-二噻唑，通过 4,5-二氯-1,2,3-二噻唑氯化物（阿佩尔盐）的简洁合成方法获得。针对猫免疫缺陷病毒 (FIV) 感染的细胞筛选了一系列小型化合物库作为 HIV 模型。这种方法突出了对结构活性关系的新理解，并导致开发具有降低毒性的亚微摩尔抗病毒化合物。此外，通过先进的 QM-MM 建模可以深入了解该系统的机械进展。1,2,3-二噻唑代表一种多功能支架，具有进一步开发治疗 FIV 和 HIV 的潜力。
• English, Russell F.; Rakitin, Oleg A.; Rees, Charles W., Journal of the Chemical Society. Perkin transactions I, 1997, # 3, p. 201 - 205
  作者：English, Russell F.、Rakitin, Oleg A.、Rees, Charles W.、Vlasova, Olga G.

  DOI：——

  日期：——
• Reactions of 5-(arylimino)-4-chloro-5H-1,2,3-dithiazoles with primary and secondary alkylamines: novel synthesis of (arylimino)cyanomethyl alkylamino disulfides and their mechanisms of formation
  作者：Hyunil Lee、Kyongtae Kim

  DOI：10.1021/jo00077a017

  日期：1993.12

  Reactions of 5-(arylimino)-4-chloro-5H-1,2,3-dithiazoles with alkylamines such as isopropylamine, piperidine, pyrrolidine, and diethylamine in methylene chloride at room temperature gave (arylimino)cyanomethyl alkylamino disulfides (14-83%) along with N'-aryl-N-alkylcyanoformamidines (O-88%). The yields of the latter increase and those of the former decrease with the concentration of the amine. In addition, some of the latter compounds were independently synthesized by treatment of the former with cyclic amines such as piperidine, pyrrolidine, and morpholine in methylene chloride at room temperature (22-97%). The results indicate that the former compounds are involved as intermediates in the formation of the latter in these reactions. However, when [(p-nitrophenyl)-imino] cyanomethyl (pentane-1,5-diyl)amino disulfide was treated with sterically bulky amines such as tert-butyl- and diethylamines at reflux and room temperature, respectively, cyanoformamidines having a piperidine moiety rather than tert-butyl- and diethylamino groups were obtained as the only isolable products. Two pathways which involve initially either direct nucleophilic attack of alkylamines on the imino carbon or on the sulfur a to the amino group of (arylimino)cyanomethyl alkylamino disulfides are proposed to rationalize the results.