(5Z)-5-(3-bromobenzylidene)-2-thioxo-1,3-thiazolidin-4-one | 34709-47-2

• 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: (5Z)-5-(3-bromobenzylidene)-2-thioxo-1,3-thiazolidin-4-one
• 英文别名: 5-(m-Bromobenzyliden)rhodanin；5-(3-bromo-benzylidene)-2-thioxo-thiazolidin-4-one；5-(3-Brom-benzyliden)-2-thioxo-thiazolidin-4-on；(5Z)-5-[(3-bromophenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one
• CAS: 34709-47-2
• 化学式: C₁₀H₆BrNOS₂
• 分子量: 300.2
• InChiKey: OTYMLMRHOPDJMX-YVMONPNESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  86.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  罗丹宁 、 间溴苯甲醛 在 哌啶 作用下， 以 乙醇 为溶剂， 以92%的产率得到(5Z)-5-(3-bromobenzylidene)-2-thioxo-1,3-thiazolidin-4-one
  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

• PDZ-Domain Modulators
  申请人：Joshi Mangesh

  公开号：US20090204336A1

  公开（公告）日：2009-08-13

  The invention relates to compounds which bind to the PDZ domains of proteins with PDZ domains, the uses of such compounds and screening methods for identification of such compounds.
• [EN] THIAZOLIDINEDIONES<br/>[FR] THIAZOLIDINEDIONES
  申请人：SMITHKLINE BEECHAM CORP

  公开号：WO2002062337A1

  公开（公告）日：2002-08-15

  This invention relates to novel thiazolidinediones and their use as anti-bacterials
• 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.