3-[2-(4-methoxyphenyl)ethyl]-2-sulfanylidene-1,3-thiazolidin-4-one

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-[2-(4-methoxyphenyl)ethyl]-2-sulfanylidene-1,3-thiazolidin-4-one
• 英文别名: 3-(4-methoxy-phenethyl)-2-thioxo-thiazolidin-4-one；3-(4-Methoxy-phenaethyl)-2-thioxo-thiazolidin-4-on
• 化学式: C₁₂H₁₃NO₂S₂
• mdl: MFCD10040386
• 分子量: 267.373
• InChiKey: XKQMYYNWVQQGPH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  86.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-[2-(4-methoxyphenyl)ethyl]-2-sulfanylidene-1,3-thiazolidin-4-one 在 sodium acetate 、 溶剂黄146 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 240.0h， 生成 3-[2-(4-methoxyphenyl)ethyl]-5-[4-(2-phenyl1,10b-dihydropyrazolo[1,5-c][1,3]benzoxazin-5-yl)-benzylidene]-2-sulfanylidene-1,3-thiazolidin-4-one
  参考文献：
  名称：

  Synthesis and Biological Activity of Pyrazolo[1,5-c][1,3]benzoxazines Containing a Thiazolidin-4-one Fragment

  摘要：

  5-[4-(2-Aryl-1,10b-dihydropyrazolo[1,5-c][1,3]benzoxazin-5-yl)benzylidene]-1,3-thiazolidin-4-ones were synthesized by reactions of 4-[(3-R-2,4-dioxo-1,3-thiazolidin-5-ylidene)methyl]benzaldehydes with 2-(3-aryl-4,5-dihydro-1H-pyrazol-5-yl)phenols and evaluated for antitumor and anti-inflammatory activities.

  DOI：

  10.1134/s1070428020040053
• 作为产物：
  描述：

  (4-methoxy-phenethylthiocarbamoylsulfanyl)-acetic acid 在 溶剂黄146 作用下， 生成 3-[2-(4-methoxyphenyl)ethyl]-2-sulfanylidene-1,3-thiazolidin-4-one
  参考文献：
  名称：

  RHODANINES. I. DERIVATIVES OF β-PHENYLETHYLAMINES

  摘要：

  DOI：

  10.1021/ja01358a034

文献信息

• Novel broad spectrum virucidal molecules against enveloped viruses
  作者：Valeria Cagno、Cristina Tintori、Andrea Civra、Roberta Cavalli、Marika Tiberi、Lorenzo Botta、Annalaura Brai、Giulio Poli、Caroline Tapparel、David Lembo、Maurizio Botta

  DOI：10.1371/journal.pone.0208333

  日期：——

  Viral infections are an important cause of death worldwide. Unfortunately, there is still a lack of antiviral drugs or vaccines for a large number of viruses, and this represents a remarkable challenge particularly for emerging and re-emerging viruses. For this reason, the identification of broad spectrum antiviral compounds provides a valuable opportunity for developing efficient antiviral therapies. Here we report on a class of rhodanine and thiobarbituric derivatives displaying a broad spectrum antiviral activity against seven different enveloped viruses including an HSV-2 acyclovir resistant strain with favorable selectivity indexes. Due to their selective action on enveloped viruses and to their lipid oxidation ability, we hypothesize a mechanism on the viral envelope that affects the fluidity of the lipid bilayer, thus compromising the efficiency of virus-cell fusion and preventing viral entry.

  病毒感染是全球死亡的一个重要原因。遗憾的是，目前仍然缺乏针对大量病毒的抗病毒药物或疫苗，这对新出现和再次出现的病毒来说尤其是一个巨大的挑战。因此，鉴定广谱抗病毒化合物为开发高效的抗病毒疗法提供了宝贵的机会。在此，我们报告了一类罗丹宁和硫代巴比妥衍生物，它们对七种不同的包膜病毒（包括一种对 HSV-2 阿昔洛韦耐药的病毒株）具有广谱抗病毒活性，并具有良好的选择性指标。由于它们对包膜病毒的选择性作用及其脂质氧化能力，我们推测病毒包膜上存在一种影响脂质双分子层流动性的机制，从而影响病毒细胞融合的效率并阻止病毒进入。
• Synthesis and in vitro anticancer potential of new thiazole-containing derivatives of rhodanine
  作者：Oleksandr V. Los、Vitalii O. Sinenko、Oleksandr L. Kobzar、Victor V. Zhirnov、Andriy I. Vovk、Volodymyr S. Brovarets

  DOI：10.1007/s10593-023-03220-z

  日期：2023.7

  3-thiazol-2-yl-, 1,3-thiazol-4-yl-, and 1,3-thiazol-5-yl-containing derivatives of N-arylalkyl- and N-carboxyalkyl-substituted rhodanines were synthesized via Knoevenagel condensation and tested against 60 cancer cell lines of NCI panel. Among these compounds, N-[2-(4-methoxyphenyl)ethyl], N-[2-(3,4-dimethoxyphenyl)ethyl], and N-carboxydecyl rhodanines with 1,3-thiazol-4-yl or 1,3-thiazol-5-yl fragments were

  合成了N-芳烷基-和N-羧烷基取代的绕丹宁的新含 1,3-噻唑-2-基-、1,3-噻唑-4-基-和 1,3-噻唑-5-基的衍生物通过Knoevenagel 浓缩并针对 NCI 小组的 60 种癌细胞系进行了测试。这些化合物中，N- [2-(4-甲氧基苯基)乙基]、N- [2-(3，4-二甲氧基苯基)乙基]和N-羧基癸基绕丹宁与1，3-噻唑-4-基或1， 3-噻唑-5-基片段是最有效的试剂，导致该组中超过 50% 的个体系生长受到抑制。它们的活性通过 50% 生长抑制的计算平均值来表征（GI 50)、总生长抑制 (TGI) 和 50% 细胞杀伤 (LC 50 )。对于整个组的敏感细胞系，带有N -[2-(4-甲氧基苯基)乙基]和N -[2-(3,4-二甲氧基苯基)乙基]取代基的化合物的平均 GI 50和平均 TGI 相似，并且具有N-羧基癸基取代基的化合物显着降低。含1，3-噻唑-5-基的N
• SAR and 3D-QSAR Studies on Thiadiazolidinone Derivatives:  Exploration of Structural Requirements for Glycogen Synthase Kinase 3 Inhibitors
  作者：Ana Martinez、Mercedes Alonso、Ana Castro、Isabel Dorronsoro、J. Luis Gelpí、F. Javier Luque、Concepción Pérez、Francisco J. Moreno

  DOI：10.1021/jm040895g

  日期：2005.11.1

  The 2,4-disubstituted thiadiazolidinones (TDZD) are described as the first ATP-noncompetitive GSK-3 inhibitors. Following an SAR study about TDZD, different structural modifications in the heterocyclic ring aimed to test the influence of each heteroatom on the biological study are here reported here. Various compounds such as hydantoins, dithiazolidindiones, rhodanines, maleimides, and triazoles were synthesized and screened as GSK-3 inhibitors. After an extensive SAR study among these different heterocyclic families, TDZDs have been revealed as a privileged scaffold for the selective inhibition of GSK-3. A CoMFA analysis was also performed highlighting the molecular electrostatic field interaction in the interaction of TDZDs with GSK-3. Moreover, first mapping studies indicate two binding modes which in turn might imply relevant differences in the mechanism that underly the inhibitory activity of TDZDs.
• Synthesis and Biological Activity of Pyrazolo[1,5-c][1,3]benzoxazines Containing a Thiazolidin-4-one Fragment
  作者：V. Y. Horishny、L. Z. Mandzyuk、R. Z. Lytvyn、O. V. Bodnarchuk、V. S. Matiychuk、M. D. Obushak

  DOI：10.1134/s1070428020040053

  日期：2020.4

  5-[4-(2-Aryl-1,10b-dihydropyrazolo[1,5-c][1,3]benzoxazin-5-yl)benzylidene]-1,3-thiazolidin-4-ones were synthesized by reactions of 4-[(3-R-2,4-dioxo-1,3-thiazolidin-5-ylidene)methyl]benzaldehydes with 2-(3-aryl-4,5-dihydro-1H-pyrazol-5-yl)phenols and evaluated for antitumor and anti-inflammatory activities.
• RHODANINES. I. DERIVATIVES OF β-PHENYLETHYLAMINES
  作者：Johannes S. Buck、Clifford S. Leonard

  DOI：10.1021/ja01358a034

  日期：1931.7