4-[(4-oxo-3-((tetrahydrofuran-2-yl)methyl)-2-thioxothiazolidin-5-ylidene)methyl]benzoic acid | 1474053-28-5

• 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: 4-[(4-oxo-3-((tetrahydrofuran-2-yl)methyl)-2-thioxothiazolidin-5-ylidene)methyl]benzoic acid
• CAS: 1474053-28-5
• 化学式: C₁₆H₁₅NO₄S₂
• 分子量: 349.431
• InChiKey: FNVHUKMRFQLQLA-JYRVWZFOSA-N

物化性质

• 沸点：
  556.6±60.0 °C(Predicted)
• 密度：
  1.50±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.77
• 重原子数：
  23.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  66.84
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  4-[(4-oxo-3-((tetrahydrofuran-2-yl)methyl)-2-thioxothiazolidin-5-ylidene)methyl]benzoic acid 、 N-alpha-芴甲氧羰基-N-epsilon-叔丁氧羰基-L-赖氨酸 、 芴甲氧羰酰基正亮氨酸 、 Fmoc-Pbf-L-精氨酸 在 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 、 哌啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 N-[(2S)-1-[[(2S)-6-amino-1-[[(2S)-1-amino-1-oxohexan-2-yl]amino]-1-oxohexan-2-yl]amino]-5-(diaminomethylideneamino)-1-oxopentan-2-yl]-4-[(Z)-[4-oxo-3-(oxolan-2-ylmethyl)-2-sulfanylidene-1,3-thiazolidin-5-ylidene]methyl]benzamide
  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
• 作为产物：
  描述：

  3-(tetrahydrofuran-2-ylmethyl)-2-thioxo-1,3-thiazolidin-4-one 、 对醛基苯甲酸 在 ammonium acetate 、 溶剂黄146 作用下， 反应 0.08h， 以87%的产率得到4-[(4-oxo-3-((tetrahydrofuran-2-yl)methyl)-2-thioxothiazolidin-5-ylidene)methyl]benzoic acid
  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