((5Z)-5-{[5-(4-methoxyphenyl)-2-furyl]methylene}-4-oxo-2-thioxo-1,3-thiazolidin-3-yl)acetic acid | 1427538-40-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: ((5Z)-5-{[5-(4-methoxyphenyl)-2-furyl]methylene}-4-oxo-2-thioxo-1,3-thiazolidin-3-yl)acetic acid
• 英文别名: 2-{(5Z)-5-{[5-(4-methoxyphenyl)furan-2-yl]methylidene}-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl}acetic acid；2-[(5Z)-5-[[5-(4-methoxyphenyl)furan-2-yl]methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]acetic acid
• CAS: 1427538-40-6
• 化学式: C₁₇H₁₃NO₅S₂
• 分子量: 375.426
• InChiKey: RMYNLYNJRHVJNU-ZSOIEALJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  137
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  5-(4-甲氧基苯基)-2-糠醛 、 3-羧甲基绕丹宁 在 哌啶 作用下， 以 乙醇 为溶剂， 以51%的产率得到((5Z)-5-{[5-(4-methoxyphenyl)-2-furyl]methylene}-4-oxo-2-thioxo-1,3-thiazolidin-3-yl)acetic acid
  参考文献：
  名称：

  Rational design of apoptosis signal-regulating kinase 1 inhibitors: Discovering novel structural scaffold

  摘要：

  Increased activity of apoptosis signal-regulating kinase 1 (ASK1) is associated with a number of human disorders and the inhibitors of ASK1 may become important compounds for pharmaceutical application. Here we report novel ASK1 inhibitor scaffold, namely 5-(5-Phenyl-furan-2-ylmethylene)-2-thioxo-thiazolidin-4-one, that has been identified using virtual screening and biochemical tests. A series of derivatives has been synthesized and evaluated in vitro towards human protein kinase ASK1. It was revealed that the most active compounds 4-((5Z)-5-{[5-(4-bromophenyl)-2-furyl]methylene}-4-oxo-2-thioxo-1,3-thiazolidin-3-yl)butanoic acid and 6-((5Z)-5-{[5-(4-bromophenyl)-2-furyl]methylene}-4-oxo-2-thioxo-1,3-thiazolidin-3-yl)hexanoic acid inhibit ASK1 with IC50 of 0.2 mu M. Structure activity relationships of 33 derivatives of 5-(5-Phenyl-furan-2-ylmethylene)-2-thioxo-thiazolidin-4-one have been studied and binding mode of this chemical class has been predicted. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.09.022

文献信息

• [EN] A HIGH-THROUGHPUT ASSAY FOR IDENTIFYING SMALL MOLECULES THAT MODULATE AMP-ACTIVATED PROTEIN KINASE (AMPK)<br/>[FR] DOSAGE À HAUT RENDEMENT POUR IDENTIFIER DE PETITES MOLÉCULES QUI MODULENT LA PROTÉINE KINASE ACTIVÉE PAR L'AMP (AMPK)
  申请人：UNIV NORTH CAROLINA

  公开号：WO2016025023A1

  公开（公告）日：2016-02-18

  The present invention provides an in vitro method for identifying a compound that modulates adenosine monophosphate-activated protein kinase (AMPK) for the manufacture of a diagnostic or therapeutic agent. The present invention further provides an assay for identifying a compound that modulates AMPK.

  本发明提供了一种体外方法，用于鉴定调节腺苷单磷酸激活蛋白激酶（AMPK）的化合物，以制造诊断或治疗剂。本发明进一步提供了一种用于鉴定调节AMPK的化合物的检测方法。
• High-Throughput Assay for Identifying Small Molecules that Modulate AMP-activated Protein Kinase (AMPK)
  申请人：North Carolina Central University

  公开号：US20160176859A1

  公开（公告）日：2016-06-23

  The present invention provides an in vitro method for identifying a compound that modulates adenosine monophosphate-activated protein kinase (AMPK) for the manufacture of a diagnostic or therapeutic agent. The present invention further provides an assay for identifying a compound that modulates AMPK.

  本发明提供了一种体外方法，用于鉴定调节腺苷酸单磷酸激活蛋白激酶（AMPK）的化合物，以制备诊断或治疗制剂。本发明还提供了一种用于鉴定调节AMPK的化合物的测定方法。
• [EN] A HIGH-THROUGHPUT ASSAY FOR IDENTIFYING SMALL MOLECULES THAT MODULATE AMP-ACTIVATED PROTEIN KINASE (AMPK)<br/>[FR] DOSAGE À HAUT DÉBIT PERMETTANT D'IDENTIFIER DE PETITES MOLÉCULES QUI MODULENT LA PROTÉINE KINASE ACTIVÉE PAR AMP (AMPK)
  申请人：UNIV NORTH CAROLINA

  公开号：WO2015023827A1

  公开（公告）日：2015-02-19

  The present invention provides an in vitro method for identifying a compound that modulates adenosine monophosphate-activated protein kinase (AMPK) for the manufacture of a diagnostic or therapeutic agent. The present invention further provides an assay for identifying a compound that modulates AMPK.
• Rational design of apoptosis signal-regulating kinase 1 inhibitors: Discovering novel structural scaffold
  作者：Galyna P. Volynets、Volodymyr G. Bdzhola、Andriy G. Golub、Anatoliy R. Synyugin、Maksym A. Chekanov、Oleksandr P. Kukharenko、Sergiy M. Yarmoluk

  DOI：10.1016/j.ejmech.2012.09.022

  日期：2013.3

  Increased activity of apoptosis signal-regulating kinase 1 (ASK1) is associated with a number of human disorders and the inhibitors of ASK1 may become important compounds for pharmaceutical application. Here we report novel ASK1 inhibitor scaffold, namely 5-(5-Phenyl-furan-2-ylmethylene)-2-thioxo-thiazolidin-4-one, that has been identified using virtual screening and biochemical tests. A series of derivatives has been synthesized and evaluated in vitro towards human protein kinase ASK1. It was revealed that the most active compounds 4-((5Z)-5-[5-(4-bromophenyl)-2-furyl]methylene}-4-oxo-2-thioxo-1,3-thiazolidin-3-yl)butanoic acid and 6-((5Z)-5-[5-(4-bromophenyl)-2-furyl]methylene}-4-oxo-2-thioxo-1,3-thiazolidin-3-yl)hexanoic acid inhibit ASK1 with IC50 of 0.2 mu M. Structure activity relationships of 33 derivatives of 5-(5-Phenyl-furan-2-ylmethylene)-2-thioxo-thiazolidin-4-one have been studied and binding mode of this chemical class has been predicted. (C) 2012 Elsevier Masson SAS. All rights reserved.