2-(benzo[d]thiazol-2-ylimino)-5-(4-hydroxy-3,5-dimethoxybenzylidene)thiazolidine-4-one | 1056198-98-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2-(benzo[d]thiazol-2-ylimino)-5-(4-hydroxy-3,5-dimethoxybenzylidene)thiazolidine-4-one
• 英文别名: 5-(4-hydroxy-3,5-dimethoxybenzylidene)-2-(benzo[d]thiazol-2-ylimino)thiazolidin-4-one；2-(1,3-benzothiazol-2-ylamino)-5-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]-1,3-thiazol-4-one
• CAS: 1056198-98-1
• 化学式: C₁₉H₁₅N₃O₄S₂
• 分子量: 413.478
• InChiKey: WTYRLPROOFMPEA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.75
• 重原子数：
  28.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  96.53
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为产物：
  描述：

  N-(1,3-苯并噻唑-2-基)-2-氯乙酰胺 在 sodium acetate 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 4.0h， 生成 2-(benzo[d]thiazol-2-ylimino)-5-(4-hydroxy-3,5-dimethoxybenzylidene)thiazolidine-4-one
  参考文献：
  名称：

  Fragment-based design, docking, synthesis, biological evaluation and structure–activity relationships of 2-benzo/benzisothiazolimino-5-aryliden-4-thiazolidinones as cycloxygenase/lipoxygenase inhibitors

  摘要：

  Balanced modulation of several targets is one of the current strategies for the treatment of multi-factorial diseases. Based on the knowledge of inflammation mechanisms, it was inferred that the balanced inhibition of cyclooxygenase-1/cyclooxygenase-2/lipoxygenase might be a promising approach for treatment of such a multifactorial disease state as inflammation. Detection of fragments responsible for interaction with enzyme's binding site provides the basis for designing new molecules with increased affinity and selectivity. A new chemoinformatics approach was proposed and applied to create a fragment library that was used to design novel inhibitors of cycloxygenase-1/cycloxygenase-2/lipoxygenase enzymes. Potential binding sites were elucidated by docking. Synthesis of novel compounds, and the in vitro/in vivo biological testing confirmed the results of computational studies. The benzothiazolyl moiety was proved to be of great significance for developing more potent inhibitors. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.10.029

文献信息

• Rational Use of Heterogeneous Data in Quantitative Structure–Activity Relationship (QSAR) Modeling of Cyclooxygenase/Lipoxygenase Inhibitors
  作者：Alexey A. Lagunin、Athina Geronikaki、Phaedra Eleftheriou、Pavel V. Pogodin、Alexey V. Zakharov

  DOI：10.1021/acs.jcim.8b00617

  日期：2019.2.25

  Numerous studies have been published in recent years with acceptable quantitative structure-activity relationship (QSAR) modeling based on heterogeneous data. In many cases, the training sets for QSAR modeling were constructed from compounds tested by different biological assays, contradicting the opinion that QSAR modeling should be based on the data measured by a single protocol. We attempted to

  近年来，已经发表了许多基于异构数据的可接受的定量构效关系（QSAR）模型的研究。在许多情况下，用于QSAR建模的训练集是由通过不同生物学测定法测试的化合物构建的，这与认为QSAR建模应基于单一协议所测得的数据的观点相矛盾。我们试图开发一些方法来帮助确定应如何使用异类数据来创建QSAR模型，该方法基于针对同一目标和同一终点通过不同实验方法测试的不同化合物集。为此，使用GUSAR软件创建了从ChEMBL数据库获得的100多个QSAR模型，用于与环氧化酶1,2（COX）和种子脂氧化酶（LOX）相互作用的配体的IC50值。在外部装置上测试了QSAR模型，其中包括26种新的噻唑烷酮衍生物，并通过实验测试了其对COX-1,2 / LOX的抑制作用。对于LOX，衍生物的IC50值从89μM到26μM，对于COX-1从200μM到0.018μM，对于COX-2从210μM到1μM。这项研究表明，模型的准确
• One-pot reactions in the synthesis of thiazolidinone derivatives by nano-Fe₃O₄–cysteine catalyst
  作者：Halimeh Hajighasemi、Naser Foroughifar、Alireza Khajeh-Amiri、Ebrahim Balali

  DOI：10.1080/17415993.2022.2089038

  日期：2022.11.2

  A simple and efficient one-pot approach for assembling some benzylidene-2-(benzo[d]thiazol-2-ylimino) thiazolidin-4-one derivatives utilizing Fe3O4–cysteine as an efficient catalyst via reaction between benzo[d]thiazol-2-amine, ammonium thiocyanate, chloroacetyl chloride, and aromatic aldehydes, in EtOH at 80°C, is reported. Minimize chemical waste, time-saving, simplify practical aspects besides the

  一种简单有效的一锅法组装一些亚苄基-2-(苯并[ d ]噻唑-2-基亚氨基)噻唑烷-4-酮衍生物，利用Fe 3 O 4 -半胱氨酸作为有效催化剂，通过苯并[ d ]之间的反应据报道，噻唑-2-胺、硫氰酸铵、氯乙酰氯和芳香醛，在 80°C 的 EtOH 中。除了良好的官能团耐受性和纳米催化剂易于分离之外，最大限度地减少化学废物、节省时间、简化实际方面是本方法的突出特点。合成化合物对金黄色葡萄球菌ATCC 25923的体外抗菌筛选，对不同浓度的样品（200、100、50、25、12.5、5.25 和 3.12 µg/ml）进行表皮葡萄球菌ATCC 1446、蜡状芽孢杆菌ATCC 1247、大肠杆菌ATCC 1399 和铜绿假单胞菌ATCC 1430，并测量了最低最低抑菌浓度、最低杀菌浓度、区域抑菌量，并研究了生物膜的形成。
• 2-Thiazolylimino/Heteroarylimino-5-arylidene-4-thiazolidinones as New Agents with SHP-2 Inhibitory Action
  作者：A. Geronikaki、P. Eleftheriou、P. Vicini、I. Alam、A. Dixit、A. K. Saxena

  DOI：10.1021/jm8004306

  日期：2008.9.11

  SHP-2, a nonreceptor protein tyrosine phosphatase encoded by the PTPN11 gene, mediates cell signaling by growth factors and cytokines via the RAS/MAP kinase pathway. Somatic mutations in PTPN11 gene account for approximately 18% of juvenile myelomonocytic leukemia (JMML) patients. Moreover, SHP-2 mutations leading to continuously active enzyme were found in more than 50% of Noonan syndrome patients and are considered to be responsible for the high tendency of these patients to juvenile leukemias and other cancer types. Recently SHP-2 became a new drug target, but till flow little has been done in this field. In the present study, 172-thiazolylimino/heteroarylimino-5-arylidene-4-thiazolidinones divided into three series of derivatives bearing thiazole-, benzo[d]thiazole-, and benzo[d]isothizole rings were tested for SHP-2 inhibitory activity. Most of the compounds were good SHP-2 inhibitors. Benzo[d]thiazole derivatives exhibited the best inhibitory action. Docking studies revealed that hydrophobic interactions and hydrogen bond formation stabilize enzyme-inhibitor complex.