(Z)-5-(2-fluorobenzylidene)thiazolidine-2,4-dione | 1001669-87-9

• 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: (Z)-5-(2-fluorobenzylidene)thiazolidine-2,4-dione
• 英文别名: (5Z)-5-[(2-fluorophenyl)methylidene]-1,3-thiazolidine-2,4-dione
• CAS: 1001669-87-9
• 化学式: C₁₀H₆FNO₂S
• 分子量: 223.228
• InChiKey: HWSHSFNYTZXIGL-YVMONPNESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  71.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2,4-噻唑烷二酮 、 2-氟苯甲醛 在 乙二胺 作用下， 反应 0.5h， 以49%的产率得到(Z)-5-(2-fluorobenzylidene)thiazolidine-2,4-dione
  参考文献：
  名称：

  Tau-Centric Multitarget Approach for Alzheimer’s Disease: Development of First-in-Class Dual Glycogen Synthase Kinase 3β and Tau-Aggregation Inhibitors

  摘要：

  Several findings propose the altered tau protein network as an important target for Alzheimer's disease (AD). Particularly, two points of pharmacological intervention can be envisaged: inhibition of phosphorylating tau kinase GSK-3 beta and tau aggregation process. On the basis of this consideration and on our interest in multitarget paradigms in AD, we report on the discovery of 2,4-thiazolidinedione derivatives endowed with such a profile. 28 and 30 displayed micromolar IC50 values toward GSK-3 beta, together with the capacity of inhibiting AcPHF6 aggregation of 60% and 80% at 10 ktM, respectively. In addition, they showed PAMPA-BBB permeability, together with a suitable cellular safety profile. 30 also displayed inhibition of both K18 and full-length tau aggregations. Finally, both compounds were able to improve cell viability in an okadaic acid-induced neurodegeneration cell model. To the best of our knowledge, 28 and 30 are the first balanced, nontoxic, dual-acting compounds hitting tau cascade at two different hubs.

  DOI：

  10.1021/acs.jmedchem.8b00610

文献信息

• Pharmaceutical Preparations Comprising Insulin, Zinc Ions and Zinc-Binding Ligand
  申请人：Kaarsholm Niels Christian

  公开号：US20090123563A1

  公开（公告）日：2009-05-14

  Novel preparations comprising branched ligands for the HisB10 Zn2+ sites of the R-state insulin hexamer. The preparations have a prolonged action designed for flexible injection regimes.

  这段话的中文翻译如下：使用分支配体的新型制备物，用于R-状态胰岛素六聚体的HisB10 Zn2+位点。这些制备物具有长效作用，旨在为灵活的注射方案设计。
• BENZYLIDENE-THIAZOLIDINEDIONES AND ANALOGUES AND THEIR USE IN THE TREATMENT OF INFLAMMATION
  申请人：Maxia Pharmaceuticals, Inc.

  公开号：EP1214305A1

  公开（公告）日：2002-06-19
• PHARMACEUTICAL COMPOSITIONS COMPRISING INSULIN AND LEGENDS OF INSULIN HEXAMER
  申请人：NOVO NORDISK A/S

  公开号：EP1585541B1

  公开（公告）日：2007-11-14
• [EN] BENZYLIDENE-THIAZOLIDINEDIONES AND ANALOGUES AND THEIR USE IN THE TREATMENT OF INFLAMMATION<br/>[FR] BENZYLIDENE-THIAZOLIDINEDIONES ET ANALOGUES ET LEUR UTILISATION POUR LE TRAITEMENT DE L'INFLAMMATION
  申请人：MAXIA PHARMACEUTICALS INC

  公开号：WO2001016123A1

  公开（公告）日：2001-03-08

  The present invention relates to certain substituted heterocycles of Formula (I) which may be useful in the treatment of diseases related to uncontrolled proliferation, such as lymphoma, Hodgkin's Disease, leukemia, breast cancer, prostate cancer or cancers in general; and inflammation, such as osteoarthritis, rheumatoid arthritis, Crohn's Disease or Inflammatory Bowel Disease.