2,5-dimethoxy-N-(4-chloro-5H-1,2,3-dithiazol-5-ylidene)aniline

• 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: 2,5-dimethoxy-N-(4-chloro-5H-1,2,3-dithiazol-5-ylidene)aniline
• 英文别名: 2,5-dimethoxy-N-(4-chloro-5H-dithiazol-5-ylidene)-aniline
• 化学式: C₁₀H₉ClN₂O₂S₂
• 分子量: 288.779
• InChiKey: DXMBBLQZGMHXSZ-BENRWUELSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.11
• 重原子数：
  17.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  43.71
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  2,5-dimethoxy-N-(4-chloro-5H-1,2,3-dithiazol-5-ylidene)aniline 在 sodium hydroxide 作用下， 以 甲苯 为溶剂， 反应 11.5h， 生成 4,7-二甲氧基-1,3-苯并噻唑-2-羧酸
  参考文献：
  名称：

  Synthesis and in vitro antitumour evaluation of benzothiazole-2-carbonitrile derivatives

  摘要：

  Novel benzothiazole derivatives have been synthesised via the corresponding imino-1,2,3-dithiazoles. The cytotoxicity of some of these polyheterocyclic compounds was studied. Our results show that 2-cyano derivatives exhibit a medium in vitro antitumour activity. (C) 1999 Editions scientifiques et medicales Elsevier SAS.

  DOI：

  10.1016/s0223-5234(99)00130-0
• 作为产物：
  描述：

  4,5-二氯-1,2,3-二噻唑氯化物 、 2,5-二甲氧基苯胺 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 2,5-dimethoxy-N-(4-chloro-5H-1,2,3-dithiazol-5-ylidene)aniline
  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

• Rapid Synthesis of 2-Cyanobenzothiazoles from<i>N</i>-Aryliminodithiazoles Under Microwave Irradiation
  作者：Valérie Bénéteau、Thierry Besson、Charles W. Rees

  DOI：10.1080/00397919708003382

  日期：1997.7

  Microwave irradiation of neat N-arylimino-1,2,3-dithiazoles 2 in screw-capped glass vials gives 2-cyanobenzothiazoles 3, rapidly and cleanly in good yield.
• Eco-Friendly Microwave-Assisted Scaleable Synthesis of 2-Cyanobenzothiazoles via<b><i>N</i></b>-Arylimino-1,2,3-dithiazoles
  作者：Stéphane Frère、Valérie Thiéry、Thierry Besson

  DOI：10.1081/scc-120025190

  日期：2003.11

  The cyclization procedure of N-aryl iminodithiazoles into 2-cyanobenzothiazoles was re-investigated with the aim to develop original and environmentally friendly procedures. In this article, the benefits associated with the microwave methodology are reported and the opportunity to use solvent-free procedures in order to scale up organic synthesis is studied. The result obtained show that the strong thermal effects due to graphite/microwaves interaction can be efficiently used for the synthesis of heterocyclic molecules for which traditional methods failed or are less attractive.
• Synthesis and in vitro antitumour evaluation of benzothiazole-2-carbonitrile derivatives
  作者：Valérie Bénéteau、Thierry Besson、Jérôme Guillard、Stéphane Léonce、Bruno Pfeiffer

  DOI：10.1016/s0223-5234(99)00130-0

  日期：1999.12

  Novel benzothiazole derivatives have been synthesised via the corresponding imino-1,2,3-dithiazoles. The cytotoxicity of some of these polyheterocyclic compounds was studied. Our results show that 2-cyano derivatives exhibit a medium in vitro antitumour activity. (C) 1999 Editions scientifiques et medicales Elsevier SAS.
• Novel 6-substituted benzothiazol-2-yl indolo[1,2-c]quinazolines and benzimidazo[1,2-c]quinazolines
  作者：Stéphane Frère、Valérie Thiéry、Christian Bailly、Thierry Besson

  DOI：10.1016/s0040-4020(02)01593-4

  日期：2003.2

  The synthetic route to and a preliminary biological evaluation of novel indolo[1,2-c]quinazolines (8) and benzimidazo[1,2-c]quinazolines (9) are described. The products were obtained by condensation of the appropriate diamines (e.g. 2-(2-aminophenyl)indole or 2-(2-aminophenyl)benzimidazole) with 2-cyanobenzothiazoles. This work further demonstrates the general applicability of microwaves for a facile

  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。