3-(4-methoxybenzyl)thiazolidine-2,4-dione | 943114-29-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-(4-methoxybenzyl)thiazolidine-2,4-dione
• 英文别名: 2,4-Thiazolidinedione, 3-[(4-methoxyphenyl)methyl]-；3-[(4-methoxyphenyl)methyl]-1,3-thiazolidine-2,4-dione
• CAS: 943114-29-2
• 化学式: C₁₁H₁₁NO₃S
• mdl: MFCD27983030
• 分子量: 237.279
• InChiKey: HTPPYGDEBULXCD-UHFFFAOYSA-N

物化性质

• 熔点：
  92-95 °C(Solv: ethanol (64-17-5))
• 沸点：
  387.1±44.0 °C(Predicted)
• 密度：
  1.359±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.272
• 拓扑面积：
  71.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(4-methoxybenzyl)thiazolidine-2,4-dione 在 Schwartz's reagent 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成
  参考文献：
  名称：

  Schwartz reagent mediated synthesis of thiazolones and imidazolones from thiazolidine-2,4-diones and imidazolidine-2,4-diones

  摘要：

  A novel reduction/elimination method of thiazolidine-2,4-dione and imidazolidine-2,4-dione derivatives using Schwartz reagent to synthesize numerous thiazolones and imidazolones in a single step is reported. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.12.015
• 作为产物：
  描述：

  1,3-thiazolidine-2,4-dione potassium salt 、 alkaline earth salt of/the/ methylsulfuric acid 以 N,N-二甲基甲酰胺 为溶剂， 以84%的产率得到3-(4-methoxybenzyl)thiazolidine-2,4-dione
  参考文献：
  名称：

  Thiazolidinone–Peptide Hybrids as Dengue Virus Protease Inhibitors with Antiviral Activity in Cell Culture

  摘要：

  The protease of dengue virus is a promising target for antiviral drug discovery. We here report a new generation of peptide hybrid inhibitors of dengue protease that incorporate N-substituted 5-arylidenethiazolidinone heterocycles (rhodanines and thiazolidinediones) as N-terminal capping groups of the peptide moiety. The compounds were extensively characterized with respect to inhibition of various proteases, inhibition mechanisms, membrane permeability, antiviral activity, and cytotoxicity in cell culture. A sulfur/oxygen exchange in position 2 of the capping heterocycle (thiazolidinedione-capped vs rhodanine-capped peptide hybrids) has a significant effect on these properties and activities. The most promising in vitro affinities were observed for thiazolidinedione-based peptide hybrids containing hydrophobic groups with K-i values between 1.5 and 1.8 mu M and competitive inhibition mechanisms. Rhodanine-capped peptide hybrids with hydrophobic substituents have, in correlation with their membrane permeability, a more pronounced antiviral activity in cell culture than the thiazolidinediones.

  DOI：

  10.1021/jm400828u

文献信息

• [EN] UBIQUITINATION MODULATORS<br/>[FR] MODULATEURS D'UBIQUITINATION
  申请人：ITI SCOTLAND LTD

  公开号：WO2011135303A2

  公开（公告）日：2011-11-03

  The use of compounds or pharmaceutically acceptable derivatives thereof which are ubiquitin modulators, in methods of treating cancer, inflammatory diseases, neurodegenerative diseases and/or cardiovascular diseases is described.
• Thiazolidinone–Peptide Hybrids as Dengue Virus Protease Inhibitors with Antiviral Activity in Cell Culture
  作者：Christoph Nitsche、Verena N. Schreier、Mira A. M. Behnam、Anil Kumar、Ralf Bartenschlager、Christian D. Klein

  DOI：10.1021/jm400828u

  日期：2013.11.14

  The protease of dengue virus is a promising target for antiviral drug discovery. We here report a new generation of peptide hybrid inhibitors of dengue protease that incorporate N-substituted 5-arylidenethiazolidinone heterocycles (rhodanines and thiazolidinediones) as N-terminal capping groups of the peptide moiety. The compounds were extensively characterized with respect to inhibition of various proteases, inhibition mechanisms, membrane permeability, antiviral activity, and cytotoxicity in cell culture. A sulfur/oxygen exchange in position 2 of the capping heterocycle (thiazolidinedione-capped vs rhodanine-capped peptide hybrids) has a significant effect on these properties and activities. The most promising in vitro affinities were observed for thiazolidinedione-based peptide hybrids containing hydrophobic groups with K-i values between 1.5 and 1.8 mu M and competitive inhibition mechanisms. Rhodanine-capped peptide hybrids with hydrophobic substituents have, in correlation with their membrane permeability, a more pronounced antiviral activity in cell culture than the thiazolidinediones.
• Schwartz reagent mediated synthesis of thiazolones and imidazolones from thiazolidine-2,4-diones and imidazolidine-2,4-diones
  作者：Srinivasa Reddy Dandepally、Radouane Elgoummadi、Alfred L. Williams

  DOI：10.1016/j.tetlet.2012.12.015

  日期：2013.2

  A novel reduction/elimination method of thiazolidine-2,4-dione and imidazolidine-2,4-dione derivatives using Schwartz reagent to synthesize numerous thiazolones and imidazolones in a single step is reported. (C) 2012 Elsevier Ltd. All rights reserved.