2-hydroxy-5-(4-oxo-2-thioxo-1,3-thiazolidin-3-yl)benzoic acid | 872827-08-2

• 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: 2-hydroxy-5-(4-oxo-2-thioxo-1,3-thiazolidin-3-yl)benzoic acid
• 英文别名: 2-hydroxy-5-(4-oxo-2-thioxothiazolidin-3-yl)benzoic acid；N-(3-carboxy-4-hydroxyphenyl)rhodanine；2-Hydroxy-5-(4-oxo-2-thioxo-thiazolidin-3-yl)benzoic acid；2-hydroxy-5-(4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl)benzoic acid
• CAS: 872827-08-2
• 化学式: C₁₀H₇NO₄S₂
• 分子量: 269.302
• InChiKey: CCRZSJKHTMPUPZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  135
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-hydroxy-5-(4-oxo-2-thioxo-1,3-thiazolidin-3-yl)benzoic acid 、 对甲酰基苯甲酸甲酯 在 哌啶 作用下， 以 乙醇 为溶剂， 以76%的产率得到2-hydroxy-5-{(5Z)-5-[4-(methoxycarbonyl)benzylidene]-4-oxo-2-thioxo-1,3-thiazolidin-3-yl}benzoic 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
• 作为产物：
  描述：

  双(羧甲基)三硫代碳酸盐 、 5-氨基水杨酸 以 水 、 N,N-二甲基甲酰胺 、 异丙醇 为溶剂， 反应 5.0h， 以61%的产率得到2-hydroxy-5-(4-oxo-2-thioxo-1,3-thiazolidin-3-yl)benzoic acid
  参考文献：
  名称：

  5-Indolylmethylen-4-oxo-2-thioxothiazolidine 衍生物的合成、生物学评价和分子对接研究

  摘要：

  背景：传染病是对公共卫生安全的重大全球压力，并对全世界的社会经济稳定产生影响。对当前抗菌治疗的耐药性增加导致迫切需要发现和开发具有不同作用模式的感染性治疗的新实体，这些实体可以针对敏感和耐药菌株。方法：使用经典的有机化学方法合成化合物。使用 PASS 和基于 PASS 的网络应用程序进行生物活性谱的预测。LigandScout 软件中的药效团建模用于抗菌活性的定量建模。使用微量稀释法评估抗菌活性。自动停靠 4。2® 软件用于阐明所研究化合物的可能的细菌和真菌分子靶标。结果：所有化合物对所有测试的细菌都表现出比氨苄青霉素更好的抗菌效力。三种化合物针对耐药菌株 MRSA、铜绿假单胞菌和大肠杆菌进行了测试，发现它们比 MRSA 比参考药物更有效。所有化合物都表现出比参考药物联苯苄唑（6-17 倍）和酮康唑（13-52 倍）更高程度的抗真菌活性。可以考虑将三种最活跃的化合物用于进一步开发新的、更有效的抗菌剂。结论：

  DOI：

  10.3390/molecules27031068

文献信息

• Plasminogen Activator Inhibitor-1 Inhibitor
  申请人：Muto Susumu

  公开号：US20070276011A1

  公开（公告）日：2007-11-29

  A medicament having inhibitory activity against plasminogen activator inhibitor-1, which comprises as an active ingredient a compound represented by the following general formula (I) or a salt thereof: wherein R 1 and R 2 represents an aromatic group which may be substituted, W represents a group selected from the following connecting group W-1: (wherein a bond at the left end binds to the carbon atom and a bond at the right end binds to the nitrogen atom, X represents sulfur atom or NH, Y represents oxygen atom or sulfur atom, R 3 represents a hydrocarbon group, hydroxy group, or carboxy group), Z represents a single bond or a connecting group wherein a number of atoms in a main chain is 1 to 3.

  一种具有抑制纤溶酶原激活物抑制剂-1活性的药物，其包含以下通式（I）或其盐作为活性成分的化合物：其中R1和R2代表可以被取代的芳香基团，W代表以下连接基团之一：（其中左端的键结合到碳原子，右端的键结合到氮原子，X代表硫原子或NH，Y代表氧原子或硫原子，R3代表烃基团，羟基或羧基），Z代表单键或连接基团，其中主链中的原子数为1到3。
• Design, Synthesis, and Biological Evaluation of <i>N</i>-Carboxyphenylpyrrole Derivatives as Potent HIV Fusion Inhibitors Targeting gp41
  作者：Kun Liu、Hong Lu、Ling Hou、Zhi Qi、Cátia Teixeira、Florent Barbault、Bo-Tao Fan、Shuwen Liu、Shibo Jiang、Lan Xie

  DOI：10.1021/jm800869t

  日期：2008.12.25

  On the basis of the structures of small-molecule hits targeting the HIV-1 gp41, N-(4-carboxy-3-hydi-oxy)plieiiyl-2,5-dimethylpyl-role (2, NB-2), and N-(3-carboxy-4-chloro)phenylpyrrole (A(1), NB-64), 42 N-carboxyphenylpyrrole derivatives in two categories (A and B series) were designed and synthesized. We found that I I compounds exhibited promising anti-HIV-1 activity at micromolar level and their antiviral activity was correlated with their inhibitory activity on gp41 six-helix bundle formation, suggesting that these compounds block HIV fusion and entry by disrupting gp41 core formation. The structure-activity relationship and molecular docking analysis revealed that the carboxyl group Could interact with either Arg579 or Lys574 to form salt bridges and two methyl groups on the pyrrole ring were favorable for interaction with the residues in gp41 pocket. The most active compound, N-(3-carboxy-4-hydroxy)phenyl-2,5-dimethylpyrrole (A(12)), partially occupied the deep hydrophobic pocket, suggesting that enlarging the molecular size of A(12) could improve its binding affinity and anti-HIV-1 activity for further development as a small-molecule HIV fusion and entry inhibitor.
• 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.
• Synthesis, Biological Evaluation and Molecular Docking Studies of 5-Indolylmethylen-4-oxo-2-thioxothiazolidine Derivatives
  作者：Volodymyr Horishny、Athina Geronikaki、Victor Kartsev、Vasyl Matiychuk、Anthi Petrou、Pavel Pogodin、Vladimir Poroikov、Theodora A. Papadopoulou、Ioannis S. Vizirianakis、Marina Kostic、Marija Ivanov、Marina Sokovic

  DOI：10.3390/molecules27031068

  日期：——

  Compounds were synthesized using the classical organic chemistry methods. Prediction of biological activity spectra was carried out using PASS and PASS-based web applications. Pharmacophore modeling in LigandScout software was used for quantitative modeling of the antibacterial activity. Antimicrobial activity was evaluated using the microdilution method. AutoDock 4.2® software was used to elucidate probable

  背景：传染病是对公共卫生安全的重大全球压力，并对全世界的社会经济稳定产生影响。对当前抗菌治疗的耐药性增加导致迫切需要发现和开发具有不同作用模式的感染性治疗的新实体，这些实体可以针对敏感和耐药菌株。方法：使用经典的有机化学方法合成化合物。使用 PASS 和基于 PASS 的网络应用程序进行生物活性谱的预测。LigandScout 软件中的药效团建模用于抗菌活性的定量建模。使用微量稀释法评估抗菌活性。自动停靠 4。2® 软件用于阐明所研究化合物的可能的细菌和真菌分子靶标。结果：所有化合物对所有测试的细菌都表现出比氨苄青霉素更好的抗菌效力。三种化合物针对耐药菌株 MRSA、铜绿假单胞菌和大肠杆菌进行了测试，发现它们比 MRSA 比参考药物更有效。所有化合物都表现出比参考药物联苯苄唑（6-17 倍）和酮康唑（13-52 倍）更高程度的抗真菌活性。可以考虑将三种最活跃的化合物用于进一步开发新的、更有效的抗菌剂。结论：