3-(2-hydroxyethyl)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: 3-(2-hydroxyethyl)thiazolidine-2,4-dione
• 英文别名: 3-(2-hydroxyethyl)-1,3-thiazolidine-2,4-dione
• 化学式: C₅H₇NO₃S
• 分子量: 161.181
• InChiKey: PJOQCYGCTXGPBK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  82.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(2-hydroxyethyl)thiazolidine-2,4-dione 在 4-二甲氨基吡啶 、 potassium carbonate 、 三乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 16.0h， 生成 tert-butyl 4-(2-(2,4-dioxothiazolidin-3-yl)ethyl)piperazine-1-carboxylate
  参考文献：
  名称：

  通过促进 β-连环蛋白和 Ras 降解治疗结直肠癌的新型 Ras 调节剂的结构优化

  摘要：

  Ras 蛋白一直被认为是抗癌治疗的一个迷人靶点，因为它的功能异常与癌症密切相关。然而，由于无法通过控制 Ras 激活机制来调节其故障，Ras 一直被认为是不可药用的。最近，针对 G12C 突变的 Lumakras 获得批准，Ras 在抗癌治疗中的治疗兴趣重新焕发活力。在这里，我们展示了一系列化合物，这些化合物通过利用 Wnt/β-catenin 通路与 Ras 之间关系的独特作用机制来抑制 Ras。KYA1797K (1)结合 axin 以稳定导致 Ras 磷酸化和随后降解的 β-catenin 破坏复合物，类似于典型的 β-catenin 调节。基于1的化学结构, 我们进行了结构优化并确定 3-(2-hydroxyethyl)-5-((6-(4-nitrophenyl)pyridin-2-yl)methylene)thiazolidine-2,4-dione ( 13d ) 为最有效的化合物

  DOI：

  10.1016/j.bioorg.2022.106234
• 作为产物：
  描述：

  2-巯基噻唑啉 、 溴乙酰溴 在 sodium hydride 作用下， 以 二氯甲烷 为溶剂， 以20%的产率得到3-(2-hydroxyethyl)thiazolidine-2,4-dione
  参考文献：
  名称：

  Synthesis of N-substituted 2,4-thiazolidinediones from oxazolidinethiones

  摘要：

  A novel reaction has been found between oxazolidinethione and bromoacetyl bromide to afford N-substituted 2,4-thiazolidinediones through an intramolecular nucleophilic substitution reaction. Interestingly a step of elimination was carried out in trisubstituted oxazolidinethiones forming a double bond. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.09.116

文献信息

• FUSED RING COMPOUND CONTAINING FURAN OR SALT THEREOF AND PHARMACEUTICAL COMPOSITION COMPRISING SAME
  申请人：YUHAN CORPORATION

  公开号：US20150191478A1

  公开（公告）日：2015-07-09

  The present invention provides a fused ring compound containing furan or a pharmaceutically acceptable salt thereof, a method for preparing same, a pharmaceutical composition comprising same, and a use thereof. The fused ring compound containing furan or a pharmaceutically acceptable salt thereof inhibits the activity of phosphatidylinositol 3-kinase (PI3K) and can therefore be used in a pharmaceutical composition for treating and preventing respiratory diseases, inflammatory diseases, proliferative diseases, cardiovascular diseases, or central nervous system diseases which occur due to the over-activation of PI3K.

  本发明提供一种含有呋喃或其药用可接受盐的融环化合物，以及制备该化合物的方法、包含该化合物的药物组合物和其用途。含有呋喃或其药用可接受盐的融环化合物抑制磷脂酰肌醇3-激酶（PI3K）的活性，因此可用于制备治疗和预防由于PI3K过度活化而引起的呼吸道疾病、炎症性疾病、增殖性疾病、心血管疾病或中枢神经系统疾病的药物组合物。
• SUBSTITUTED THIAZOLIDINEDIONE INDAZOLES, INDOLES AND BENZOTRIAZOLES AS ESTROGEN-RELATED RECEPTOR-a MODULATORS
  申请人：Bignan Gilles

  公开号：US20110294780A1

  公开（公告）日：2011-12-01

  The present invention relates to compounds of Formula (I), methods for preparing these compounds, compositions, intermediates and derivatives thereof and for treating a condition including but not limited to ankylosing spondylitis, artherosclerosis, arthritis (such as rheumatoid arthritis, infectious arthritis, childhood arthritis, psoriatic arthritis, reactive arthritis), bone-related diseases (including those related to bone formation), breast cancer (including those unresponsive to anti-estrogen therapy), cardiovascular disorders, cartilage-related disease (such as cartilage injury/loss, cartilage degeneration, and those related to cartilage formation), chondrodysplasia, chondrosarcoma, chronic back injury, chronic bronchitis, chronic inflammatory airway disease, chronic obstructive pulmonary disease, diabetes, disorders of energy homeostasis, gout, pseudogout, lipid disorders, metabolic syndrome, multiple myeloma, obesity, osteoarthritis, osteogenesis imperfecta, osteolytic bone metastasis, osteomalacia, osteoporosis, Paget's disease, periodontal disease, polymyalgia rheumatica, Reiter's syndrome, repetitive stress injury, hyperglycemia, elevated blood glucose level, and insulin resistance.

  本发明涉及式（I）的化合物，制备这些化合物的方法，组合物，中间体和衍生物，以及治疗包括但不限于强直性脊柱炎，动脉硬化，关节炎（如类风湿性关节炎，感染性关节炎，儿童关节炎，银屑病性关节炎，反应性关节炎），与骨相关的疾病（包括与骨形成有关的疾病），乳腺癌（包括对抗雌激素治疗无效的乳腺癌），心血管疾病，软骨相关疾病（如软骨损伤/丧失，软骨退化以及与软骨形成有关的疾病），软骨发育不良，软骨肉瘤，慢性背部损伤，慢性支气管炎，慢性炎症性气道疾病，慢性阻塞性肺疾病，糖尿病，能量平衡失调的疾病，痛风，假性痛风，脂质代谢紊乱，代谢综合征，多发性骨髓瘤，肥胖症，骨关节炎，成骨不全症，骨转移性溶骨症，软骨软化症，骨质疏松症，帕吉特病，牙周病，多肌痛性类风湿，Reiter综合征，重复性应力损伤，高血糖，血糖水平升高和胰岛素抵抗等疾病的治疗。
• Substituted thiazolidinedione indazoles, indoles and benzotriazoles as estrogen-related receptor-α modulators
  申请人：Bignan Gilles

  公开号：US08796256B2

  公开（公告）日：2014-08-05

  The present invention relates to compounds of Formula (I), methods for preparing these compounds, compositions, intermediates and derivatives thereof and for treating a condition including but not limited to ankylosing spondylitis, artherosclerosis, arthritis (such as rheumatoid arthritis, infectious arthritis, childhood arthritis, psoriatic arthritis, reactive arthritis), bone-related diseases (including those related to bone formation), breast cancer (including those unresponsive to anti-estrogen therapy), cardiovascular disorders, cartilage-related disease (such as cartilage injury/loss, cartilage degeneration, and those related to cartilage formation), chondrodysplasia, chondrosarcoma, chronic back injury, chronic bronchitis, chronic inflammatory airway disease, chronic obstructive pulmonary disease, diabetes, disorders of energy homeostasis, gout, pseudogout, lipid disorders, metabolic syndrome, multiple myeloma, obesity, osteoarthritis, osteogenesis imperfecta, osteolytic bone metastasis, osteomalacia, osteoporosis, Paget's disease, periodontal disease, polymyalgia rheumatica, Reiter's syndrome, repetitive stress injury, hyperglycemia, elevated blood glucose level, and insulin resistance.

  本发明涉及化合物I式，制备这些化合物的方法，组成物，中间体和衍生物以及治疗包括但不限于强直性脊柱炎，动脉粥样硬化，关节炎（如类风湿性关节炎，感染性关节炎，儿童关节炎，银屑病性关节炎，反应性关节炎），与骨相关的疾病（包括与骨形成有关的疾病），乳腺癌（包括对抗雌激素治疗无效的乳腺癌），心血管疾病，软骨相关疾病（如软骨损伤/丢失，软骨退化以及与软骨形成有关的疾病），软骨发育不良，软骨肉瘤，慢性背部损伤，慢性支气管炎，慢性炎症性气道疾病，慢性阻塞性肺疾病，糖尿病，能量稳态失调疾病，痛风，假性痛风，脂质代谢异常，代谢综合征，多发性骨髓瘤，肥胖症，骨关节炎，成骨不全症，骨转移性溶骨病，骨软化症，骨质疏松症，Paget病，牙周病，多肌痛性类风湿，Reiter综合征，重复性应力损伤，高血糖，血糖升高和胰岛素抵抗等疾病的方法。
• Thiazolidinone–Peptide Hybrids as Dengue Virus Protease Inhibitors with Antiviral Activity in Cell Culture
  作者：Christoph Nitsche、Verena N. Schreier、Mira A. M. Behnam、Anil Kumar、Ralf Bartenschlager、Christian D. Klein

  DOI：10.1021/jm400828u

  日期：2013.11.14

  The protease of dengue virus is a promising target for antiviral drug discovery. We here report a new generation of peptide hybrid inhibitors of dengue protease that incorporate N-substituted 5-arylidenethiazolidinone heterocycles (rhodanines and thiazolidinediones) as N-terminal capping groups of the peptide moiety. The compounds were extensively characterized with respect to inhibition of various proteases, inhibition mechanisms, membrane permeability, antiviral activity, and cytotoxicity in cell culture. A sulfur/oxygen exchange in position 2 of the capping heterocycle (thiazolidinedione-capped vs rhodanine-capped peptide hybrids) has a significant effect on these properties and activities. The most promising in vitro affinities were observed for thiazolidinedione-based peptide hybrids containing hydrophobic groups with K-i values between 1.5 and 1.8 mu M and competitive inhibition mechanisms. Rhodanine-capped peptide hybrids with hydrophobic substituents have, in correlation with their membrane permeability, a more pronounced antiviral activity in cell culture than the thiazolidinediones.
• 3,5-Disubstituted-thiazolidine-2,4-dione analogs as anticancer agents: Design, synthesis and biological characterization
  作者：Kai Liu、Wei Rao、Hardik Parikh、Qianbin Li、Tai L. Guo、Steven Grant、Glen E. Kellogg、Shijun Zhang

  DOI：10.1016/j.ejmech.2011.10.031

  日期：2012.1

  A series of 2,5-disubstituted-thiazolidine-2,4-dione analogs based on the newly identified lead 1, a potential anticancer agent via the inhibition of the Raf/MEK/extracellular signal regulated kinase (ERK) and phosphatidylinositol 3-kinase (PI3K)/Akt signaling cascades, were synthesized and biologically characterized. A new lead structure, 15, was identified to have improved anti-proliferative activities in U937 cells, to induce apoptosis in U937, M12 and DU145 cancer cells, and to arrest U937 cells at the S-phase. Furthermore, Western blot analysis demonstrated a correlation of the anti-proliferative activity and blockade of the Raf/MEK/ERK and PI3K/Akt signaling pathways. Collectively, these results strongly encourage further optimization of 15 as a new lead with multi-target properties to develop more potent compounds as anticancer agents. (C) 2011 Elsevier Masson SAS. All rights reserved.