3-chloro-benzyl-thiazolidine-2,4-dione | 848606-44-0

• 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-chloro-benzyl-thiazolidine-2,4-dione
• 英文别名: 3-[(3-Chlorophenyl)methyl]-2,4-thiazolidinedione；3-[(3-chlorophenyl)methyl]-1,3-thiazolidine-2,4-dione
• CAS: 848606-44-0
• 化学式: C₁₀H₈ClNO₂S
• 分子量: 241.698
• InChiKey: TWGJAOKOHILERB-UHFFFAOYSA-N

物化性质

• 沸点：
  376.8±44.0 °C(Predicted)
• 密度：
  1.487±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  62.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-chloro-benzyl-thiazolidine-2,4-dione 、 ethyl 3-([1,1'-biphenyl]-4-yl)-2-cyanoacrylate 在 哌啶 作用下， 以 乙醇 为溶剂， 以73%的产率得到5-biphenyl-4-ylmethylene-3-(3-chloro-benzyl)-thiazolidine-2,4-dione
  参考文献：
  名称：

  Synthesis and anti-inflammatory activity of new arylidene-thiazolidine-2,4-diones as PPARγ ligands

  摘要：

  Eight new 5-arylidene-3-benzyl-thiazolidine-2,4-diones with halide groups on their benzyl rings were synthesized and assayed in vivo to investigate their anti-inflammatory activities. These compounds showed considerable biological efficacy when compared to rosiglitazone, a potent and well-known agonist of PPAR gamma, which was used as a reference drug. This suggests that the substituted 5-arylidene and 3-benzylidene groups play important roles in the anti-inflammatory properties of this class of compounds. Docking studies with these compounds indicated that they exhibit specific interactions with key residues located in the site of the PPAR gamma structure, which corroborates the hypothesis that these molecules are potential ligands of PPAR gamma. In addition, competition binding assays showed that four of these compounds bound directly to the ligand-binding domain of PPAR gamma, with reduced affinity when compared to rosiglitazone. An important trend was observed between the docking scores and the anti-inflammatory activities of this set of molecules. The analysis of the docking results, which takes into account the hydrophilic and hydrophobic interactions between the ligands and the target, explained why the 3-(2-bromobenzyl)-5-(4-methanesulfonyl-benzylidene)-thiazolidine-2,4-dione compound had the best activity and the best docking score. Almost all of the stronger hydrophilic interactions occurred between the substituted 5-arylidene group of this compound and the residues of the binding site. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.04.045
• 作为产物：
  描述：

  2,4-噻唑烷二酮 、 3-氯苄溴 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 3-chloro-benzyl-thiazolidine-2,4-dione
  参考文献：
  名称：

  新型5-[（（1 H-吲哚-3-基）亚甲基]噻唑烷-2,4-二酮-[1,2,3]三唑杂化物的合成及抗菌活性

  摘要：

  通过点击化学反应合成了5-[（1 H-吲哚-3-基）亚甲基]噻唑烷-2,4-二酮-[1,2,3]三唑杂化衍生物，并筛选了对革兰氏阳性和革兰氏阴性的抗菌活性细菌和真菌种类。所有合成的化合物均通过1 H和13 C NMR，IR和MS光谱表征。抗菌研究表明，几种产品显示出高活性，某些产品被确定为潜在的抗真菌活性剂。

  DOI：

  10.1134/s107036321702027x

文献信息

• Synthesis and antimicrobial activity of novel 5-[(1H-indol-3-yl)methylene]thiazolidine-2,4-dione–[1,2,3]triazole hybrids
  作者：L. Kamala、B. S. Veena、P. V. Anantha Lakshmi、P. Vasantha、E. Sujatha

  DOI：10.1134/s107036321702027x

  日期：2017.2

  ]thiazolidine-2,4-dione–[1,2,3]triazole hybrid derivatives were synthesized by click chemistry reaction and screened for antimicrobial activity against Gram positive and Gram negative bacteria and fungal species. All synthesized compounds were characterized by 1H and 13C NMR, IR and MS spectra. Antibacterial study indicated that several products demonstrated high activity and some products were determined

  通过点击化学反应合成了5-[（1 H-吲哚-3-基）亚甲基]噻唑烷-2,4-二酮-[1,2,3]三唑杂化衍生物，并筛选了对革兰氏阳性和革兰氏阴性的抗菌活性细菌和真菌种类。所有合成的化合物均通过1 H和13 C NMR，IR和MS光谱表征。抗菌研究表明，几种产品显示出高活性，某些产品被确定为潜在的抗真菌活性剂。
• 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。
• Structural exploration, synthesis and pharmacological evaluation of novel 5-benzylidenethiazolidine-2,4-dione derivatives as iNOS inhibitors against inflammatory diseases
  作者：Liang Ma、Heying Pei、Lei Lei、Linhong He、Jinying Chen、Xiaolin Liang、Aihua Peng、Haoyu Ye、Mingli Xiang、Lijuan Chen

  DOI：10.1016/j.ejmech.2014.12.036

  日期：2015.3

  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.
• Alam, Sarfaraz; Chinthala, Yakaiah; Domatti, Anand Kumar, Indian Journal of Heterocyclic Chemistry, 2021, vol. 31, # 4, p. 567 - 575
  作者：Alam, Sarfaraz、Chinthala, Yakaiah、Domatti, Anand Kumar、Khan, Feroz、Kumar, A. Niranjana、Kumar, J. Kotesh、Srinivas, K. V. N. S.、Tiwari, Ashok Kumar

  DOI：——

  日期：——