3-[2-(2,4-dichloro-phenyl)-2-oxo-ethyl]-thiazolidine-2,4-dione | 949000-95-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-[2-(2,4-dichloro-phenyl)-2-oxo-ethyl]-thiazolidine-2,4-dione
• 英文别名: 3-[(2,4-Dichlorobenzoyl)methyl]thiazolidine-2,4-dione；3-[2-(2,4-dichlorophenyl)-2-oxoethyl]-1,3-thiazolidine-2,4-dione
• CAS: 949000-95-7
• 化学式: C₁₁H₇Cl₂NO₃S
• 分子量: 304.153
• InChiKey: KOXRXCDBHCBHST-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  79.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-[2-(2,4-dichloro-phenyl)-2-oxo-ethyl]-thiazolidine-2,4-dione 、 4-氯-2-(4-吗啉)-5-噻唑甲醛 在 sodium acetate 、 溶剂黄146 作用下， 反应 5.0h， 以55%的产率得到5-((4-chloro-2-(morpholin-4-yl)-1,3-thiazol-5-yl)methylidene)-3-(2-(2,4-dichlorophenyl)-2-oxoethyl)thiazolidine-2,4-dione
  参考文献：
  名称：

  Synthesis and antidiabetic activity of morpholinothiazolyl-2,4-thiazolidindione derivatives

  摘要：

  We report the synthesis and the in vitro insulin releasing and glucose uptake activity of the morpholino thiazolyl-2,4-thiazolidinediones (1-15). Compounds 5, 11-15 (at lower concentration; 0.001 mg/ml) were able to increase insulin release in the presence of 5.6 mmol/l glucose. The compounds, except derivative 3 show an increase of glucose uptake. Various compounds are interesting potential antidiabetic leads showing pancreatic and extrapancreatic effects.

  DOI：

  10.3109/14756366.2011.594047
• 作为产物：
  描述：

  1,3-thiazolidine-2,4-dione potassium salt 、 2-溴-2',4'-二氯苯乙酮 以 甲醇 为溶剂， 生成 3-[2-(2,4-dichloro-phenyl)-2-oxo-ethyl]-thiazolidine-2,4-dione
  参考文献：
  名称：

  Synthesis and antidiabetic activity of morpholinothiazolyl-2,4-thiazolidindione derivatives

  摘要：

  We report the synthesis and the in vitro insulin releasing and glucose uptake activity of the morpholino thiazolyl-2,4-thiazolidinediones (1-15). Compounds 5, 11-15 (at lower concentration; 0.001 mg/ml) were able to increase insulin release in the presence of 5.6 mmol/l glucose. The compounds, except derivative 3 show an increase of glucose uptake. Various compounds are interesting potential antidiabetic leads showing pancreatic and extrapancreatic effects.

  DOI：

  10.3109/14756366.2011.594047

文献信息

• Free radical scavenging activity of novel thiazolidine-2,4-dione derivatives
  作者：Paweł Berczyński、Irena Kruk、Teresa Piechowska、Meltem Ceylan-Unlusoy、Oya Bozdağ-Dündar、Hassan Y. Aboul-Enein

  DOI：10.1002/bio.2454

  日期：2013.11

  Free radical activity towards superoxide anion radical (), hydroxyl radical (HO•) and 2,2‐diphenyl‐1‐picrylhydrazyl (DPPH•) of a series of novel thiazolidine‐2,4‐dione derivatives (TSs) was examined using chemiluminescence, electron paramagnetic resonance (EPR) and EPR spin trapping techniques. 5,5‐Dimethyl‐1‐pyrroline‐N‐oxide (DMPO) was applied as the spin trap. Superoxide radical was produced in

  使用化学发光法检测了一系列新型噻唑烷-2,4-二酮衍生物（TSs）对超氧阴离子自由基（），羟基自由基（HO •）和2,2-二苯基-1-吡啶并肼基（DPPH •）的自由基活性，电子顺磁共振（EPR）和EPR自旋俘获技术。5,5-二甲基-1-吡咯啉-N-氧化物（DMPO）被用作自旋阱。溶于二甲亚砜的超氧化钾/ 18-冠-6醚中产生超氧化物自由基。在Fenton反应中生成了羟基自由基（Fe（II）+ H 2 O 2。发现TSs对DPPH自由基显示出轻微的清除作用（在2.5 mmol / L的浓度下减少了15-38％）和较高的清除作用（41-88％）。所测试的化合物显示出对HO •依赖性DMPO-OH自旋加合物形成的抑制作用（在2.5 mmol / L的浓度下，EPR信号的幅度下降20％至76％。我们的发现提出了对自由基具有较高反应性的新型化合物。版权所有©2012 John Wiley＆Sons，Ltd
• Plasminogen Activator Inhibitor-1 Inhibitor
  申请人：Muto Susumu

  公开号：US20070276011A1

  公开（公告）日：2007-11-29

  A medicament having inhibitory activity against plasminogen activator inhibitor-1, which comprises as an active ingredient a compound represented by the following general formula (I) or a salt thereof: wherein R 1 and R 2 represents an aromatic group which may be substituted, W represents a group selected from the following connecting group W-1: (wherein a bond at the left end binds to the carbon atom and a bond at the right end binds to the nitrogen atom, X represents sulfur atom or NH, Y represents oxygen atom or sulfur atom, R 3 represents a hydrocarbon group, hydroxy group, or carboxy group), Z represents a single bond or a connecting group wherein a number of atoms in a main chain is 1 to 3.

  一种具有抑制纤溶酶原激活物抑制剂-1活性的药物，其包含以下通式（I）或其盐作为活性成分的化合物：其中R1和R2代表可以被取代的芳香基团，W代表以下连接基团之一：（其中左端的键结合到碳原子，右端的键结合到氮原子，X代表硫原子或NH，Y代表氧原子或硫原子，R3代表烃基团，羟基或羧基），Z代表单键或连接基团，其中主链中的原子数为1到3。
• PLASMINOGEN ACTIVATOR INHIBITOR-1 INHIBITOR
  申请人：Institute of Medicinal Molecular Design, Inc.

  公开号：EP1666469A1

  公开（公告）日：2006-06-07

  A medicament having inhibitory activity against plasminogen activator inhibitor-1, which comprises as an active ingredient a compound represented by the following general formula (I) or a salt thereof: wherein R1 and R2 represents an aromatic group which may be substituted, W represents a group selected from the following connecting group W-1: (wherein a bond at the left end binds to the carbon atom and a bond at the right end binds to the nitrogen atom, X represents sulfur atom or NH, Y represents oxygen atom or sulfur atom, R3 represents a hydrocarbon group, hydroxy group, or carboxy group), Z represents a single bond or a connecting group wherein a number of atoms in a main chain is 1 to 3.

  一种对纤溶酶原激活物抑制剂-1 具有抑制活性的药物，其活性成分包括下式（I）所代表的化合物或其盐： 其中 R1 和 R2 代表可被取代的芳香基团、 W 代表选自下列连接基 W-1 的基团： (其中左端的键与碳原子结合，右端的键与氮原子结合、 X 代表硫原子或 NH Y 代表氧原子或硫原子、 R3 代表烃基、羟基或羧基）、 Z 代表单键或连接基团，其中主链中的原子数为 1 至 3。
• Mentese, Arzu; Ceylan-Uenluesoy, Meltem; Bozdag-Duendar, Oya, Arzneimittel-Forschung/Drug Research, 2009, vol. 59, # 12, p. 659 - 665
  作者：Mentese, Arzu、Ceylan-Uenluesoy, Meltem、Bozdag-Duendar, Oya、Altanlar, Nurten、Ertan, Rahmiye

  DOI：——

  日期：——
• Bozdag-Duendar, Oya; Mentese, Arzu; Verspohl, Eugen J., Arzneimittel-Forschung/Drug Research, 2008, vol. 58, # 3, p. 131 - 135
  作者：Bozdag-Duendar, Oya、Mentese, Arzu、Verspohl, Eugen J.

  DOI：——

  日期：——