5-(ethoxymethylene)thiazolidine-2,4-dione

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: 5-(ethoxymethylene)thiazolidine-2,4-dione
• 英文别名: 5-(ethoxymethylidene)-1,3-thiazolidine-2,4-dione
• 化学式: C₆H₇NO₃S
• 分子量: 173.192
• InChiKey: DZOIDBWQADXOQX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  80.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-(ethoxymethylene)thiazolidine-2,4-dione 、 氟西汀 在 三乙胺 作用下， 以 乙腈 为溶剂， 以88%的产率得到(Z)-5-((methyl(3-phenyl-3-(4-(trifluoromethyl)phenoxy)propyl)amino)methylene)thiazolidine-2,4-dione
  参考文献：
  名称：

  An assembly of structurally diverse small and simple 5-aminomethylene derivatives of 2,4-thiazolidinedione and studies of their biological activity

  摘要：

  The synthesis of a novel series of substituted 5-(aminomethylene)thiazolidine-2,4-diones was achieved using a wide range of heterocyclic models derived from eight drug-like molecules. The primary aim of this study was to combine medicinally known, biologically active molecules bearing a 2A degrees amine functionality, such as terbinafine, fluoxetine, atomoxetine, cetirizine, risperidone, aripiprazole, ziprasidone, and clopidogrel, with a thiazolidinedione ring via an amino-methylene linker. By targeting this synergistic approach to compounds with skeletal, functional, and stereochemical diversity, we have developed a simple synthetic concept to enrich the thiazolidinedione collection with various biological activities. The biological activities of the newly synthesized 5-(aminomethylene)thiazolidine-2,4-dione derivatives were explored. All compounds were found to have antibacterial activity, with compounds bearing pyridine or piperazine moieties showing good to excellent antibacterial activity. Compounds with piperazine moieties were also found to show good antifungal activity, whereas none of the synthesized compounds showed high cytotoxic activity.

  DOI：

  10.1007/s00044-015-1447-0
• 作为产物：
  描述：

  2,4-噻唑烷二酮 、 原甲酸三乙酯 在 乙酸酐 作用下， 反应 2.0h， 生成 5-(ethoxymethylene)thiazolidine-2,4-dione
  参考文献：
  名称：

  新型噻唑烷酮-双氯芬酸杂化分子的合成及生物活性评价

  摘要：

  摘要 设计并合成了一系列新型[2-(2,6-二氯苯基氨基)-苯基]-乙酸N`-3-(取代)-4-噻唑烷-5-亚基甲基-酰肼衍生物。合成化合物的结构由其 1H NMR、13C NMR 和 LCMS 光谱数据证实。根据美国 NCI 协议筛选目标化合物的体外抗癌活性、对布氏锥虫 (Tbb) 的体外杀锥虫活性，并评估对大鼠角叉菜胶水肿模型的抗炎活性。生物筛选数据导致鉴定了化合物 3.3（[2-(2,6-二氯-苯基氨基)-苯基]-乙酸 N`-(4-oxo-2-thioxo-thiazolidin-5-ylidenemethyl)-hydrazide）和3.7 ([2-(2, 6-二氯-苯氨基)-苯基]-乙酸 N`-(4-oxo-2-thioxo-3-(3-trifluoromethylphenyl)thiazolidin-5-ylidenemethyl)-hydrazide) -细胞肺癌 NCI-H522

  DOI：

  10.1080/10426507.2020.1759060

文献信息

• COMPOUND USED AS AUTOPHAGY REGULATOR, AND PREPARATION METHOD THEREFOR AND USES THEREOF
  申请人：WIGEN BIOMEDICINE TECHNOLOGY (SHANGHAI) CO., LTD.

  公开号：US20200190066A1

  公开（公告）日：2020-06-18

  It is related to compounds used as autophagy modulators and a method for preparing and using the same, specifically providing a compound of general formula (I), or pharmaceutically acceptable salts thereof, which is a type of autophagy modulators, particularly mammalian ATG8 homologues modulators.

  该内容涉及作为自噬调节剂的化合物及其制备和使用方法，具体提供了一类具有通用公式(I)的化合物，或其药用可接受盐，这是一种自噬调节剂，特别是哺乳动物ATG8同源物调节剂。
• Imidazopyridine or imidazopyrimidine compounds, their production and use
  申请人：Takeda Chemical Industries Ltd.

  公开号：US05840732A1

  公开（公告）日：1998-11-24

  This invention provides a new condensed imidazole compound possessing inhibitory activity of adhesion molecule expression. This invention also provides a therapeutic and prophylactic agent for diabetic nephritis and/or autoimmune disease and an immunosuppressor for organ transplantation.

  这项发明提供了一种新的紧缩咪唑化合物，具有抑制粘附分子表达的活性。这项发明还提供了治疗和预防糖尿病肾病和/或自身免疫疾病的药物以及器官移植的免疫抑制剂。
• Synthesis and biological activity evaluation of new thiazolidinone-diclofenac hybrid molecules
  作者：Yulia Shepeta、Andrii Lozynskyi、Marta Sulyma、Ihor Nektegayev、Philippe Grellier、Roman Lesyk

  DOI：10.1080/10426507.2020.1759060

  日期：2020.10.2

  LCMS spectroscopic data. Target compounds were screened for their in vitro anticancer activity according to US NCI protocols, in vitro trypanocidal activity toward Trypanosoma brucei brucei (Tbb) and evaluated for anti-inflammatory activity on the carrageenan edema model in rats. Biological screening data led to identification of compounds 3.3 ([2-(2,6-dichloro-phenylamino)-phenyl]-acetic acid N`-(4

  摘要 设计并合成了一系列新型[2-(2,6-二氯苯基氨基)-苯基]-乙酸N`-3-(取代)-4-噻唑烷-5-亚基甲基-酰肼衍生物。合成化合物的结构由其 1H NMR、13C NMR 和 LCMS 光谱数据证实。根据美国 NCI 协议筛选目标化合物的体外抗癌活性、对布氏锥虫 (Tbb) 的体外杀锥虫活性，并评估对大鼠角叉菜胶水肿模型的抗炎活性。生物筛选数据导致鉴定了化合物 3.3（[2-(2,6-二氯-苯基氨基)-苯基]-乙酸 N`-(4-oxo-2-thioxo-thiazolidin-5-ylidenemethyl)-hydrazide）和3.7 ([2-(2, 6-二氯-苯氨基)-苯基]-乙酸 N`-(4-oxo-2-thioxo-3-(3-trifluoromethylphenyl)thiazolidin-5-ylidenemethyl)-hydrazide) -细胞肺癌 NCI-H522
• An assembly of structurally diverse small and simple 5-aminomethylene derivatives of 2,4-thiazolidinedione and studies of their biological activity
  作者：Sandeep Mohanty、Sandeep G. Reddy、B. RamaDevi、Arun Chandra Karmakar

  DOI：10.1007/s00044-015-1447-0

  日期：2015.12

  The synthesis of a novel series of substituted 5-(aminomethylene)thiazolidine-2,4-diones was achieved using a wide range of heterocyclic models derived from eight drug-like molecules. The primary aim of this study was to combine medicinally known, biologically active molecules bearing a 2A degrees amine functionality, such as terbinafine, fluoxetine, atomoxetine, cetirizine, risperidone, aripiprazole, ziprasidone, and clopidogrel, with a thiazolidinedione ring via an amino-methylene linker. By targeting this synergistic approach to compounds with skeletal, functional, and stereochemical diversity, we have developed a simple synthetic concept to enrich the thiazolidinedione collection with various biological activities. The biological activities of the newly synthesized 5-(aminomethylene)thiazolidine-2,4-dione derivatives were explored. All compounds were found to have antibacterial activity, with compounds bearing pyridine or piperazine moieties showing good to excellent antibacterial activity. Compounds with piperazine moieties were also found to show good antifungal activity, whereas none of the synthesized compounds showed high cytotoxic activity.