[(5Z)-5-(2-furylmethylene)-4-oxo-2-thioxo-1,3-thiazolidin-3-yl]acetic acid

• 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-(2-furylmethylene)-4-oxo-2-thioxo-1,3-thiazolidin-3-yl]acetic acid
• 英文别名: (Z)-2-(5-(furan-2-ylmethylene)-4-oxo-2-thioxothiazolidin-3-yl)acetic acid；BI-9B9b；2-[(5Z)-5-(furan-2-ylmethylidene)-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]acetic acid
• 化学式: C₁₀H₇NO₄S₂
• 分子量: 269.302
• InChiKey: DFCZJGAFQKNSEX-DAXSKMNVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  128
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  糠醛 、 3-羧甲基绕丹宁 在 sodium acetate 、 溶剂黄146 、 盐酸 作用下， 以 水 为溶剂， 反应 4.0h， 以69%的产率得到[(5Z)-5-(2-furylmethylene)-4-oxo-2-thioxo-1,3-thiazolidin-3-yl]acetic acid
  参考文献：
  名称：

  罗丹宁作为开发广谱金属β-内酰胺酶抑制剂的有效支架。

  摘要：

  构造了一系列的罗丹宁，它们的Z-构型通过小分子X射线晶体结构得以证实，并测量了它们对金属-β-内酰胺酶（MβLs）的活性。获得的26个分子和硫代烯酸酯专门抑制MβLL1，IC 50范围为0.02–1.7μM，化合物2h – m表现出广谱抑制MβLsNDM-1，VIM-2，ImiS和L1的IC 50个值<16μM。所有抑制剂均增强了头孢唑林对表达L1的大肠杆菌细胞的抗菌作用，导致MIC降低了2-8倍。对接研究表明2l的硝基（NDM-1，CphA和L1）或羧基（VIM-2）配位一个或两个Zn（II）离子，而抑制剂的N-苯基增强了它与MβLs的疏水相互作用。这些研究表明，二芳基取代的罗丹酮是设计未来MβLs广谱抑制剂的良好支架。

  DOI：

  10.1021/acsmedchemlett.7b00548

文献信息

• Ultrasound accelerated solvent-free condensation reaction of rhodanines and carbonyls using Amberlyst 26 as a green and efficient base catalyst
  作者：Duc-Thuan Nguyen、Ngoc-Khoi Pham、Xuan-Triet Nguyen、Thi Xuan Thi Luu、Quynh-Nhi Nguyen Luong

  DOI：10.1080/17415993.2023.2173008

  日期：——

  The solvent-free condensation reaction of various aliphatic aldehydes, cycloalkanones, and benzaldehydes with rhodanines catalyzed by Amberlyst 26 has been reported. The catalyst's efficiency, simple work-up, simple recycling procedure, and high catalyst recyclability without any considerable change of yields several times were found to be interesting. Furthermore, the drastic acceleration of ultrasound

  已报道了 Amberlyst 26 催化的各种脂肪醛、环烷酮和苯甲醛与绕丹宁的无溶剂缩合反应。人们发现该催化剂的效率、简单的后处理、简单的回收程序以及高催化剂可回收性而收率多次没有任何显着变化，这些都是令人感兴趣的。此外，超声波照射的急剧加速被认为对于在短时间内以中等至良好的产率有效地形成亚烷基罗丹宁、环亚烷基罗丹宁和亚芳基罗丹宁。
• 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.
• Rhodanine derivatives, process for their preparation, and aldose reductase inhibitor containing the rhodanine derivatives as active ingredient
  申请人：ONO PHARMACEUTICAL CO., LTD.

  公开号：EP0047109B1

  公开（公告）日：1985-01-02
• Inhibition of lethal factor protease activity from anthrax toxin
  申请人：Pellecchia Maurizio

  公开号：US20080033025A1

  公开（公告）日：2008-02-07

  The present invention provides compounds that efficiently and specifically inhibit lethal factor (LF) protease activity of anthrax toxin.
• INHIBITION OF LETHAL FACTOR PROTEASE ACTIVITY FROM ANTHRAX TOXIN
  申请人：Pellecchia Maurizio

  公开号：US20100298390A1

  公开（公告）日：2010-11-25

  The present invention provides compounds that efficiently and specifically inhibit lethal factor (LF) protease activity of anthrax toxin.