3-phenyl-2-phenylimino-1,3-thiazolidin-4-one | 790-04-5

• 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: 3-phenyl-2-phenylimino-1,3-thiazolidin-4-one
• 英文别名: (Z)-3-phenyl-2-(phenylimino)thiazolidin-4-one；(Z)-2-phenylimino-3-phenylthiazolidin-4-one；2-phenylimino-3-phenyl-thiazolidin-4-one；2-phenylimino-3-phenylthiazolidin-4-one；3-phenyl-2-phenylimino-thiazolidin-4-one；3-Phenyl-2-phenylimino-thiazolidin-4-on
• CAS: 790-04-5
• 化学式: C₁₅H₁₂N₂OS
• mdl: MFCD00225509
• 分子量: 268.339
• InChiKey: RAVFWIXHMXTJQU-NXVVXOECSA-N

物化性质

• 熔点：
  176 °C(Solv: ethanol (64-17-5))
• 沸点：
  411.1±28.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.45
• 重原子数：
  19.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 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：

  3-phenyl-2-phenylimino-1,3-thiazolidin-4-one 、 5-溴-2-氯苯甲醛 在 potassium carbonate 作用下， 以 乙醇 、 水 为溶剂， 反应 10.0h， 生成 (Z,Z)-5-(2-chloro-5-bromobenzylidene)-3-phenyl-2-(phenylimino)thiazolidin-4-one
  参考文献：
  名称：

  Satam, Vijay; Bandi, Ravi Kumar; Behera, Ajaya Kumar, Letters in drug design and discovery, 2011, vol. 8, # 9, p. 704 - 708

  摘要：

  DOI：
• 作为产物：
  描述：

  溴乙酸 、 N,N'-二苯基硫脲 在 sodium acetate 作用下， 以 乙醇 为溶剂， 反应 6.0h， 以44.8%的产率得到3-phenyl-2-phenylimino-1,3-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

• Green and Highly Efficient One-Pot Synthesis of Some New Bis Thiazolidinones
  作者：Akbar Mobinikhaledi、Alireza Amiri

  DOI：10.2174/157017861131000059

  日期：2013.11

  A high efficient and environmentally friendly procedure for the production of bis thiazolidinones has been developed. This synthetic approach involves the simple condensation of an appropriate dialdehyde and N,N'-diarylthioureas with chloroacetyl chloride in eutectic salts as a promoter and solvent at 80 °C. All products were obtained in good to excellent yields. Structures of these compounds were established on the basis of IR, 1H-NMR, 13C-NMR and by elemental analysis.

  已经开发出一种高效且环境友好的双硫脲合成方法。该合成方法涉及在共晶盐作为促进剂和溶剂的情况下，将适当的双醛和N,N'-二芳基硫脲与氯乙酰氯在80°C下简单缩合。所有产品均以良好至优异的收率获得。这些化合物的结构通过红外光谱、1H核磁共振谱、13C核磁共振谱以及元素分析确立。
• Synthesis of 2-iminothiazolidin-4-ones using guanine functionalized SBA-16 as a solid base catalyst
  作者：Radha Gupta、Devendra Deo Pathak

  DOI：10.1016/j.tetlet.2021.153497

  日期：2021.11

  a one-pot three-component tandem annulation approach is described for the synthesis of 2-iminothiazolidin-4-ones by the reaction of aromatic/aliphatic amines, aryl isothiocyanates, and ethyl bromoacetate, catalysed by guanine-functionalized SBA-16, [SBA-16@G], as an efficient and recyclable heterogeneous solid base catalyst. The methodology is simple and offers a broad-substrate scope under mild reaction

  描述了一锅三组分串联环化方法的第一个例子，用于通过芳族/脂肪胺、异硫氰酸芳基酯和溴乙酸乙酯的反应合成 2-iminothiazolidin-4-ones，由鸟嘌呤官能化 SBA-催化16，[SBA-16@G]，作为一种高效且可回收的多相固体碱催化剂。该方法简单，在温和的反应条件下提供了广泛的底物范围。
• A highly efficient one-pot method for the synthesis of thioureas and 2-imino-4-thiazolidinones under microwave conditions
  作者：Chi-Min Chau、Tzu-Jung Chuan、Kuan-Miao Liu

  DOI：10.1039/c3ra46270f

  日期：——

  A one-pot synthesis of symmetrical and unsymmetrical substituted thioureas and 2-imino-4-thiazolidinones from simple starting materials under microwave irradiation and solventless conditions without base additives is presented. Various di- and trisubstituted thioureas are obtained in good yields in a few minutes. The sequential, three-component, one-pot synthesis of 2-imino-4-thiazolidinone derivatives is also studied, with satisfactory results obtained.

  本研究介绍了在微波辐照和无溶剂、无碱添加剂的条件下，从简单的起始原料出发，一步法合成对称和不对称取代的硫脲类化合物和 2-亚氨基-4-噻唑烷酮。各种二取代和三取代的硫脲类化合物均能在几分钟内以良好的收率获得。此外，还研究了 2-亚氨基-4-噻唑烷酮衍生物的三组份顺序一锅合成法，并取得了令人满意的结果。
• Substituted 2-Imino-5-arylidenethiazolidin-4-one Inhibitors of Bacterial Type III Secretion
  作者：Toni Kline、Heather B. Felise、Kathleen C. Barry、Stona R. Jackson、Hai V. Nguyen、Samuel I. Miller

  DOI：10.1021/jm8004515

  日期：2008.11.27

  factors that help establish and maintain infection. Disruption of such secretion systems is a potentially effective therapeutic strategy. We developed a high-throughput screen and identified a tris-aryl substituted 2-imino-5-arylidenethiazolidin-4-one, compound 1, as an inhibitor of the type III secretion system. Expansion of this chemotype enabled us to define the essential pharmacophore for type III

  多种致病性革兰氏阴性细菌利用分泌系统输出各种有助于建立和维持感染的蛋白质毒素和毒力因子。破坏这种分泌系统是一种潜在的有效治疗策略。我们开发了一个高通量的筛选器，并确定了三化合物被化合物1取代的三芳基取代的2-亚氨基5-芳基内酯-硫唑烷4-1，它是III型分泌系统的抑制剂。这种化学型的扩展使我们能够定义该结构类别用于抑制III型分泌的基本药效基团。合成多样性集帮助我们将N-3鉴定为最允许的基因座，并导致设计了一组具有改善的活性和理化性质的新型N-3-二肽修饰的同类物。现在，我们报告这些化合物的合成，
• Microwave-assisted synthesis and in-vitro anti-tumor activity of 1,3,4-triaryl-5-N-arylpyrazole-carboxamides
  作者：Hatem A. Abdel-Aziz、Heba S.A. El-Zahabi、Kamal M. Dawood

  DOI：10.1016/j.ejmech.2010.02.026

  日期：2010.6

  Regioselective 1,3-dipolar cycloaddition of nitrilimines with 5-arylidene-2-arylimino-4-thiazolidinones and with 2-(4-arylidene)thiazolo[3,2-a]benzimidazol-3(2H)-ones afforded the corresponding 1,3,4-triaryl-5-N-arylpyrazole-carboxamides and pyrazolylbenzimidazoles. All reactions were carried out under conventional thermal heating and/or microwave irradiation. Both the pyrazole-5-carboxamides and

  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。