(2Z,5Z)-5-benzylidene-3-phenyl-2-(phenylimino)thiazolidin-4-one

• 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: (2Z,5Z)-5-benzylidene-3-phenyl-2-(phenylimino)thiazolidin-4-one
• 英文别名: (Z)-5-benzylidene-3-phenyl-2-phenylimino-thiazolidin-4-one；5-benzylidene-3-phenyl-2-(phenylimino)thiazolidin-4-one；5-benzylidene-2-phenylimino-3-phenyl-thiazolidin-4-one
• 化学式: C₂₂H₁₆N₂OS
• 分子量: 356.448
• InChiKey: NUURGOCMONEDNX-GAADFGEESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  26.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  32.67
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (2Z,5Z)-5-benzylidene-3-phenyl-2-(phenylimino)thiazolidin-4-one 、 N-苯基苯羰基亚肼酰氯 在 三乙胺 作用下， 反应 0.25h， 以75%的产率得到N,1,3,4-tetraphenyl-1H-pyrazole-5-carboxamide
  参考文献：
  名称：

  1,3,4-三芳基-5- N-芳基吡唑-羧酰胺的微波辅助合成及体外抗肿瘤活性

  摘要：

  亚硝胺与5-亚芳基-2-芳基氨基-4-噻唑烷酮和2-（4-亚芳基）噻唑并[3,2 - a ]苯并咪唑-3（2 H）-的区域选择性1,3-偶极环加成反应提供了相应的1,3,4-三芳基-5- N-芳基吡唑-羧酰胺和吡唑基苯并咪唑类。所有反应均在常规热加热和/或微波辐射下进行。检查了吡唑-5-羧酰胺和吡唑基苯并咪唑对两种肿瘤细胞系Hep-2和结肠CaCo-2的体外抗肿瘤活性。大多数获得的化合物显示出对CaCo-2和Hep-2细胞系的显着活性。

  DOI：

  10.1016/j.ejmech.2010.02.026
• 作为产物：
  描述：

  N,N'-二苯基硫脲 在 sodium acetate 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 11.0h， 生成 (2Z,5Z)-5-benzylidene-3-phenyl-2-(phenylimino)thiazolidin-4-one
  参考文献：
  名称：

  Axially Chiral 2-Arylimino-3-aryl-thiazolidine-4-one Derivatives:  Enantiomeric Separation and Determination of Racemization Barriers by Chiral HPLC

  摘要：

  Axially chiral 2-arylimino-3-aryl-thiazolidine-4-ones have been synthesized as racemic mixtures, and each mixture with the exception of 2-(o-chlorophenyl)imino-3-(o-chlorophenyl)-thiazolidine-4- one has been converted to the corresponding 5-benzylidene-2-arylimino-3-aryl-thiazolidine-4-one racemates by reaction with benzaldehyde. The thermally interconvertible enantiomers of each compound have been obtained by enantioselective HPLC separation on columns Chiralpak AD-H and Chiralcel OD-H, and the barriers to racemization have been found to be 98.1-114.1 kJ/mol. The barriers determined were compared to those of structurally related compounds to provide evidence for the stereochemistry of the aryl imino bond.

  DOI：

  10.1021/jo0625554

文献信息

• Natural eutectic salts catalyzed one-pot synthesis of 5-arylidene-2-imino-4-thiazolidinones
  作者：Akbar Mobinikhaledi、Alireza Khajeh Amiri

  DOI：10.1007/s11164-012-0707-6

  日期：2013.3

  The rapid, very simple and green one-pot synthesis of 5-arylidene-2-imino-4-thiazolidinones by condensation of the thioureas with chloroacetyl chloride and an aldehyde in natural deep eutectic solvent with good to excellent yields is described.

  文中描述了一种快速、简单且环保的一锅法合成5-芳亚甲基-2-亚氨基-4-噻唑烷酮的方法，该方法通过硫脲与氯乙酰氯和一个醛在天然深共晶溶剂中缩合，产率良好至优秀。
• One-Pot Synthesis of 5-Arylidene-2-Imino-4-Thiazolidinones under Microwave Irradiation
  作者：Souad Kasmi-Mir、Ayada Djafri、Ludovic Paquin、Jack Hamelin、Mustapha Rahmouni

  DOI：10.3390/11080597

  日期：——

  A rapid and easy solvent free one-pot synthesis of 5-arylidene-2-imino-4-thiazolidinones by condensation of the thioureas with chloroacetic acid and an aldehyde under microwave-irradiation is described.

  描述了一种快速简便的无溶剂一锅法合成 5-亚芳基-2-亚氨基-4-噻唑烷酮，方法是在微波辐射下将硫脲与氯乙酸和醛缩合。
• Substituted 2-imino-1,3-thiazolidin-4-ones as N-arachidonoylethanolamine cellular uptake inhibitors
  申请人：UNIVERSITAT BERN

  公开号：US10155754B2

  公开（公告）日：2018-12-18

  The invention relates to a compound comprising the following general formula (1): and said compound for use as a medicament, in particular for use in the treatment psychiatric or neurological disorders and inflammation, in particular neuroinflammation: (formula 1) wherein each of R1, R2 and R3 are selected independently from each other from alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl, aryl, heterocycle, or heteroaryl.

  本发明涉及一种由以下通式 (1) 组成的化合物： 式 1）其中 R1、R2 和 R3 各自独立地选自烷基、烷氧基、烯基、炔基、环烷基、芳基、杂环或杂芳基。
• Phosphine-Catalyzed Construction of Sulfur Heterocycles
  作者：Sandra Gabillet、Delphine Lecerclé,、Olivier Loreau、Michael Carboni、Sophie Dézard、Jean-Marie Gomis、Frédéric Taran

  DOI：10.1021/ol701563e

  日期：2007.9.1

  A simple and efficient method for constructing sulfur heterocycles was developed using a phosphine-catalyzed tandem umpolung addition and intramolecular cyclization of bifunctional sulfur pronucleophiles on arylpropiolates. The reaction offers a promising route to synthetically useful as well as biologically active heterocycles under neutral conditions.
• Satam, Vijay; Bandi, Ravi Kumar; Behera, Ajaya Kumar, Letters in drug design and discovery, 2011, vol. 8, # 9, p. 704 - 708
  作者：Satam, Vijay、Bandi, Ravi Kumar、Behera, Ajaya Kumar、Mishra, Bijay Kumar、Brockway, Olivia、Tzou, Samuel、Zeller, Matthias、Lee, Moses、Pati, Hari

  DOI：——

  日期：——