4-([5-(4-hydroxy-3-methoxybenzylidene)-4-oxo-2-(phenylimino)thiazolidin-3-yl]methyl)benzoic acid | 1148127-02-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 4-([5-(4-hydroxy-3-methoxybenzylidene)-4-oxo-2-(phenylimino)thiazolidin-3-yl]methyl)benzoic acid
• 英文别名: 4-[5-(4-Hydroxy-3-methoxybenzylidene)-4-oxo-2-phenyliminothiazolidin-3-ylmethyl]benzoic acid；4-[[(5Z)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-4-oxo-2-phenylimino-1,3-thiazolidin-3-yl]methyl]benzoic acid
• CAS: 1148127-02-9
• 化学式: C₂₅H₂₀N₂O₅S
• 分子量: 460.51
• InChiKey: VCDVPZVCJBRQTM-OTGOLFGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  33
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  125
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  4-[(4-oxo-2-(phenylimino)thiazolidin-3-yl)methyl]benzoic acid 、 香草醛 在 哌啶 作用下， 以 乙醇 为溶剂， 反应 96.0h， 以43%的产率得到4-([5-(4-hydroxy-3-methoxybenzylidene)-4-oxo-2-(phenylimino)thiazolidin-3-yl]methyl)benzoic acid
  参考文献：
  名称：

  5-Arylidene-2-phenylimino-4-thiazolidinones as PTP1B and LMW-PTP inhibitors

  摘要：

  As part of a project aimed at identifying effective low molecular weight nonphosphorus monoanionic inhibitors of PTPs, we have synthesized 4-[(5-arylidene-4-oxo-2-phenyliminothiazolidin-3-yl) methyl]benzoic acids (4) and evaluated their inhibitory activity against human PTP1B and LMW-PTP enzymes. The introduction of a 2-phenylimino moiety onto the 4-thiazolidinone ring was designed to enhance the inhibitor/ enzyme affinity by means of further favourable interactions with residues of the active site and the surrounding loops. Some of the compounds (4a-d, f) showed interesting inhibition levels in the low micromolar range. The 5-arylidene moiety of acids 4 proved to markedly influence the potency of these inhibitors. Molecular modeling experiments inside the binding sites of both enzymes were performed. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.01.044

文献信息

• 5-Arylidene-2-phenylimino-4-thiazolidinones as PTP1B and LMW-PTP inhibitors
  作者：Rosaria Ottanà、Rosanna Maccari、Rosella Ciurleo、Paolo Paoli、Michela Jacomelli、Giampaolo Manao、Guido Camici、Christian Laggner、Thierry Langer

  DOI：10.1016/j.bmc.2009.01.044

  日期：2009.3

  As part of a project aimed at identifying effective low molecular weight nonphosphorus monoanionic inhibitors of PTPs, we have synthesized 4-[(5-arylidene-4-oxo-2-phenyliminothiazolidin-3-yl) methyl]benzoic acids (4) and evaluated their inhibitory activity against human PTP1B and LMW-PTP enzymes. The introduction of a 2-phenylimino moiety onto the 4-thiazolidinone ring was designed to enhance the inhibitor/ enzyme affinity by means of further favourable interactions with residues of the active site and the surrounding loops. Some of the compounds (4a-d, f) showed interesting inhibition levels in the low micromolar range. The 5-arylidene moiety of acids 4 proved to markedly influence the potency of these inhibitors. Molecular modeling experiments inside the binding sites of both enzymes were performed. (C) 2009 Elsevier Ltd. All rights reserved.