4-[(5-naphthalen-1-ylmethylene-4-oxo-2-(phenylimino)thiazolidin-3-yl)methyl]benzoic acid | 1148126-97-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4-[(5-naphthalen-1-ylmethylene-4-oxo-2-(phenylimino)thiazolidin-3-yl)methyl]benzoic acid
• 英文别名: 4-[(5-Naphthalen-1-ylmethylene-4-oxo-2-phenyliminothiazolidin-3-yl)methyl] benzoic acid；4-[[(5Z)-5-(naphthalen-1-ylmethylidene)-4-oxo-2-phenylimino-1,3-thiazolidin-3-yl]methyl]benzoic acid
• CAS: 1148126-97-9
• 化学式: C₂₈H₂₀N₂O₃S
• 分子量: 464.544
• InChiKey: ZWLUZLCSIPXYSX-KSVGNYRWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  34
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  95.3
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-[(3-phenyl-tioureido)methyl]benzoic acid 在 哌啶 、 三乙胺 作用下， 以 乙醇 为溶剂， 生成 4-[(5-naphthalen-1-ylmethylene-4-oxo-2-(phenylimino)thiazolidin-3-yl)methyl]benzoic acid
  参考文献：
  名称：

  5-Arylidene-4-Thiazolidinone Derivatives Active as Antidegenerative Agents on Human Chondrocyte Cultures

  摘要：

  5-芳基亚乙烯基-2-氧基-4-噻唑烷酮和2-苯基亚胺类似物被评估其在IL-1β刺激下的人类软骨细胞培养中的抗退化活性及其对基质金属蛋白酶-13的抑制能力。我们的结果表明，5-芳基亚乙烯基-4-噻唑烷酮衍生物1-9表现出抗退化活性，能够在骨关节炎过程中阻止多重软骨破坏。在选择的化合物中，(5-芳基-2,4-二氧噻唑烷-3-基)乙酸7-9在减少NO释放和恢复接受IL-1β处理的软骨细胞正常GAGs水平方面显示出显著效果。此外，苯甲酸1、5和6被证实为有效的MMP-13抑制剂，并能够恢复正常的GAGs水平。

  DOI：

  10.2174/157340613804488378

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.
• 5-Arylidene-4-Thiazolidinone Derivatives Active as Antidegenerative Agents on Human Chondrocyte Cultures
  作者：Annamaria Panico、Rosanna Maccari、Venera Cardile、Lucia Crasci、Simone Ronsisvalle、Rosaria Ottana

  DOI：10.2174/157340613804488378

  日期：2013.2.1

  5-Arylidene-2-oxo-4-thiazolidinones and 2-phenylimino analogues were evaluated for their antidegenerative activity on human chondrocyte cultures stimulated by IL-1β and for their inhibitory capability against matrix metalloproteinase- 13. Our results indicated that 5-arylidene-4-thiazolidinone derivatives 1-9 exhibit antidegenerative activity and could block multiple cartilage destruction during the osteoarthritic process. Out of the selected compounds, (5-arylidene- 2,4-dioxothiazolidin-3-yl)acetic acids 7-9 showed significant effectiveness in reducing NO release and restoring normal levels of GAGs in chondrocytes treated with IL-1β. Moreover, benzoic acids 1, 5 and 6 proved to be effective MMP-13 inhibitors and were able to restore normal levels of GAGs.

  5-芳基亚乙烯基-2-氧基-4-噻唑烷酮和2-苯基亚胺类似物被评估其在IL-1β刺激下的人类软骨细胞培养中的抗退化活性及其对基质金属蛋白酶-13的抑制能力。我们的结果表明，5-芳基亚乙烯基-4-噻唑烷酮衍生物1-9表现出抗退化活性，能够在骨关节炎过程中阻止多重软骨破坏。在选择的化合物中，(5-芳基-2,4-二氧噻唑烷-3-基)乙酸7-9在减少NO释放和恢复接受IL-1β处理的软骨细胞正常GAGs水平方面显示出显著效果。此外，苯甲酸1、5和6被证实为有效的MMP-13抑制剂，并能够恢复正常的GAGs水平。