3-(2-(dimethylamino)ethyl)thiazolidine-2,4-dione | 1569-89-7

• 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-(dimethylamino)ethyl)thiazolidine-2,4-dione
• 英文别名: 3-(2-(Dimethylamino)ethyl)thiazolidine-2,4-dione；3-[2-(dimethylamino)ethyl]-1,3-thiazolidine-2,4-dione
• CAS: 1569-89-7
• 化学式: C₇H₁₂N₂O₂S
• 分子量: 188.25
• InChiKey: QFSDPNKMGCHTQZ-UHFFFAOYSA-N

物化性质

• 沸点：
  135-138 °C(Press: 2.5 Torr)
• 密度：
  1.254±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  65.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(3-chlorophenyl)-2-(4-formylphenoxy)acetamide 、 3-(2-(dimethylamino)ethyl)thiazolidine-2,4-dione 在 哌啶 作用下， 以 乙醇 为溶剂， 反应 6.0h， 生成 (Z)-N-(3-chlorophenyl)-2-(4-((3-(2-(dimethylamino)ethyl)-2,4-dioxothiazolidin-5-ylidene)methyl)phenoxy)acetamide
  参考文献：
  名称：

  Structural exploration, synthesis and pharmacological evaluation of novel 5-benzylidenethiazolidine-2,4-dione derivatives as iNOS inhibitors against inflammatory diseases

  摘要：

  In our previous work, 3I inhibited the LPS-induced iNOS activity and NO production in RAW 264.7 cells and improved joint inflammation and cartilage destruction in inflammatory model. In this study, we synthesized 59 derivatives and bioisosteres on the basis of 3I by Knoevenagel condensation and biologically evaluated for the study of structure-activity relationship (SAR). We found that 7-44 suppressed the iNOS activity (IC50 25.2 mu M) and LPS-induced NO production (IC50 45.6 mu M) in RAW 264.7 cells. As for the SAR study, the dimethoxylphenyl group of 7-44 was potential for a further modification. At a dose of 10 mg/kg, oral administration of 7-44 possessed protective properties in both carrageenan-induced paw edema of male ICR mice and adjuvant-induced arthritis of Lewis female rats. Although the activity of 7-44 was slightly inferior, the PK profiles of 7-44 were superior to those of 3I. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.12.036
• 作为产物：
  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 3-(2-(dimethylamino)ethyl)thiazolidine-2,4-dione
  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

文献信息

• [EN] AZAINDOLE DERIVATIVES AS TYROSINE KINASE INHIBITORS<br/>[FR] DÉRIVÉS AZA-INDOLIQUES UTILISÉS COMME INHIBITEURS DE TYROSINE KINASES
  申请人：PRINCIPIA BIOPHARMA INC

  公开号：WO2012158785A1

  公开（公告）日：2012-11-22

  The present disclosure provides compounds and pharmaceutically acceptable salts that are tyrosine kinase inhibitors, in particular BLK, BMX, EGFR, HER2, HER4, ITK, JAK3, TEC, Btk, and TXK and are therefore useful for the treatment of diseases treatable by inhibition of tyrosine kinases such as cancer and inflammatory diseases such as arthritis, and the like. Also provided are pharmaceutical compositions containing such compounds and pharmaceutically acceptable salts and processes for preparing such compounds and pharmaceutically acceptable salts.

  本公开提供了一些化合物和药用盐，它们是酪氨酸激酶抑制剂，特别是BLK、BMX、EGFR、HER2、HER4、ITK、JAK3、TEC、Btk和TXK，因此适用于治疗通过抑制酪氨酸激酶治疗的疾病，如癌症和炎症性疾病（如关节炎等）。还提供了含有这些化合物和药用盐的药物组合物，以及制备这些化合物和药用盐的过程。
• AZAINDOLE DERIVATIVES AS TYROSINE KINASE INHIBITORS
  申请人：Principia Biopharma Inc.

  公开号：US20140073626A1

  公开（公告）日：2014-03-13

  The present disclosure provides compounds and pharmaceutically acceptable salts that are tyrosine kinase inhibitors, in particular BLK, BMX, EGFR, HER2, HER4, ITK, JAK3, TEC, Btk, and TXK and are therefore useful for the treatment of diseases treatable by inhibition of tyrosine kinases such as cancer and inflammatory diseases such as arthritis, and the like. Also provided are pharmaceutical compositions containing such compounds and pharmaceutically acceptable salts and processes for preparing such compounds and pharmaceutically acceptable salts.

  本公开提供了一些化合物和药学上可接受的盐，它们是酪氨酸激酶抑制剂，特别是BLK，BMX，EGFR，HER2，HER4，ITK，JAK3，TEC，Btk和TXK，因此可用于治疗通过抑制酪氨酸激酶治疗的疾病，例如癌症和炎症性疾病，如关节炎等。还提供了含有这些化合物和药学上可接受的盐的药物组合物和制备这些化合物和药学上可接受的盐的方法。
• Azaindole derivatives as tyrosine kinase inhibitors
  申请人：Goldstein David M.

  公开号：US09187487B2

  公开（公告）日：2015-11-17

  The present disclosure provides compounds and pharmaceutically acceptable salts that are tyrosine kinase inhibitors, in particular BLK, BMX, EGFR, HER2, HER4, ITK, JAK3, TEC, Btk, and TXK and are therefore useful for the treatment of diseases treatable by inhibition of tyrosine kinases such as cancer and inflammatory diseases such as arthritis, and the like. Also provided are pharmaceutical compositions containing such compounds and pharmaceutically acceptable salts and processes for preparing such compounds and pharmaceutically acceptable salts.

  本公开提供了化合物和药学上可接受的盐，它们是酪氨酸激酶抑制剂，特别是BLK、BMX、EGFR、HER2、HER4、ITK、JAK3、TEC、Btk和TXK，因此可用于治疗通过抑制酪氨酸激酶治疗的疾病，如癌症和炎症性疾病，例如关节炎等。还提供了含有这些化合物和药学上可接受的盐的制药组合物以及制备这些化合物和药学上可接受的盐的方法。
• Discovery of Dual Aβ/Tau Inhibitors and Evaluation of Their Therapeutic Effect on a <i>Drosophila</i> Model of Alzheimer’s Disease
  作者：Annachiara Gandini、Ana Elisa Gonçalves、Silvia Strocchi、Claudia Albertini、Jana Janočková、Anna Tramarin、Daniela Grifoni、Eleonora Poeta、Ondrej Soukup、Diego Muñoz-Torrero、Barbara Monti、Raimon Sabaté、Manuela Bartolini、Giuseppe Legname、Maria Laura Bolognesi

  DOI：10.1021/acschemneuro.2c00357

  日期：2022.12.7
• US9187487B2
  申请人：——

  公开号：US9187487B2

  公开（公告）日：2015-11-17