3-benzyl-5-[(Z)-(4-methoxyphenyl)methylidene]-1,3-thiazolidine-2,4-dione

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-benzyl-5-[(Z)-(4-methoxyphenyl)methylidene]-1,3-thiazolidine-2,4-dione
• 英文别名: (Z)-3-benzyl-5-(4-methoxybenzylidene)thiazolidine-2,4-dione；3-benzyl-(5Z)-(4-methoxybenzylidene)thiazolidine-2,4-dione；(5Z)-3-benzyl-5-[(4-methoxyphenyl)methylidene]-1,3-thiazolidine-2,4-dione
• 化学式: C₁₈H₁₅NO₃S
• 分子量: 325.388
• InChiKey: SKSCNLSPWGFJDZ-WJDWOHSUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  71.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-Benzyl-5-[1-(4-methoxy-phenyl)-meth-(Z)-ylidene]-2-thioxo-thiazolidin-4-one 在 碘苯二乙酸 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以67%的产率得到3-benzyl-5-[(Z)-(4-methoxyphenyl)methylidene]-1,3-thiazolidine-2,4-dione
  参考文献：
  名称：

  10.3998/ark.5550190.0018.400

  摘要：

  DOI：

  10.3998/ark.5550190.0018.400

文献信息

• Organic Reactions in Ionic Liquids;Ionic Liquid-Accelerated Three-Component Reaction: A Rapid One-PotSynthesis of 3-Alkyl-5-[(<i>Z</i>)-arylmethylidene]-1,3-thiazolidine-2,4-diones
  作者：Zhen-Chu Chen、De-Hong Yang、Song-Ying Chen、Qin-Guo Zheng

  DOI：10.1055/s-2003-40980

  日期：——

  A rapid one-pot synthesis of 3-alkyl-5-[(Z)-arylme­thylidene]-1,3-thiazolidine-2,4-dionesis described that occurs in recyclable ionic liquid [bmim]PF6 (1-butyl-3-methylimidazolium hexafluorophosphate).Significant rate enhancement and good selectivity have been observed.

  描述了在可回收离子液体 [bmim]PF6 （1-丁基-3-甲基咪唑鎓六氟磷酸盐）中快速单锅合成 3-烷基-5-[(Z)-芳基亚甲基]-1,3-噻唑烷-2,4-二酮的过程。
• Unexplored Vinylic-Substituted 5-Benzylidenethiazolidine-2,4-diones: Synthesis and DFT/NMR Stereochemical Assignment
  作者：Dorian Dupommier、Michel Boisbrun、Gerald Monard、Corinne Comoy

  DOI：10.1021/acs.joc.2c02996

  日期：2023.3.17

  alkenyl substituents was successfully introduced on the vinylic position of BTZD, and particular attention was paid to elucidate the stereochemistry of the benzylidene derivatives by using a combined DFT/NMR study.

  通过探索一种有效且通用的支架 6 功能化方法，我们研究了亚苄基噻唑烷-2,4-二酮 (BTZD) 周围新化学空间的开放。从 5-锂 TZD 开始分两步获得的 6-氯-和 6-甲酰基 BTZD 被选为关键中间体，并参与 Pd 催化的交叉偶联或 Wittig 烯烃化。在 BTZD 的乙烯基位置上成功引入了各种芳基、杂芳基或烯基取代基，并特别注意通过结合 DFT/NMR 研究阐明亚苄基衍生物的立体化学。
• Optimization of troglitazone derivatives as potent anti-proliferative agents: Towards more active and less toxic compounds
  作者：Andrea Bordessa、Christelle Colin-Cassin、Isabelle Grillier-Vuissoz、Sandra Kuntz、Sabine Mazerbourg、Gauthier Husson、Myriam Vo、Stéphane Flament、Hélène Martin、Yves Chapleur、Michel Boisbrun

  DOI：10.1016/j.ejmech.2014.06.015

  日期：2014.8

  Δ2-Troglitazone derivatives were shown to exhibit anti-proliferative activity in a PPARγ-independent manner. We prepared various compounds in order to increase their potency and decrease their toxicity towards non-malignant primary cultured hepatocytes. Many compounds induced viabilities less than 20% at 10 μM on various cancer cell lines. Furthermore, five of them showed hepatocyte viability of 80% or more at 200 μM. In addition, compounds 17 and 18 exhibited promising maximum tolerated doses on a murine model, enabling future investigations.