5-(2-(4-chlorobenzylsulfanyl)-4-chlorothiazol-5-yl-methylene)-3-(2,4-dichlorobenzyl)thiazolidine-2,4-dione | 1000417-34-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-(2-(4-chlorobenzylsulfanyl)-4-chlorothiazol-5-yl-methylene)-3-(2,4-dichlorobenzyl)thiazolidine-2,4-dione
• 英文别名: (5Z)-5-[[4-Chloro-2-[[(4-chlorophenyl)methyl]thio]-5-thiazolyl]methylene]-3-[(2,4-dichlorophenyl)methyl]-2,4-thiazolidinedione；(5Z)-5-[[4-chloro-2-[(4-chlorophenyl)methylsulfanyl]-1,3-thiazol-5-yl]methylidene]-3-[(2,4-dichlorophenyl)methyl]-1,3-thiazolidine-2,4-dione
• CAS: 1000417-34-4
• 化学式: C₂₁H₁₂Cl₄N₂O₂S₃
• 分子量: 562.348
• InChiKey: QJWSBSZXYROZLI-IUXPMGMMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.1
• 重原子数：
  32
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  129
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2-(4-chlorobenzylsulfanyl)-4-chlorothiazole-5-carbaldehyde 、 3-(2,4-二氯苄基)-1,3-噻唑烷-2,4-二酮 在 sodium acetate 、 溶剂黄146 作用下， 以61.31%的产率得到5-(2-(4-chlorobenzylsulfanyl)-4-chlorothiazol-5-yl-methylene)-3-(2,4-dichlorobenzyl)thiazolidine-2,4-dione
  参考文献：
  名称：

  Some new thiazolyl thiazolidinedione derivatives as aldose reductase inhibitors

  摘要：

  In diabetes, increased flux through the polyol pathway has been implicated in the development of diabetic complications such as cataract, retinopathy, neuropathy, and nephropathy. Aldose reductase (AR) appears to be the key factor in the reduction of glucose to sorbitol. Aldose reductase inhibitors have been found to prevent sorbitol accumulation in tissues. A series of thiazolyl-2,4-thiazolidinediones was prepared by Knoevenagel reaction of substituted benzyl-2,4-thiazolidinediones with chlorothiazolecarbaldehydes and were evaluated for their ability to inhibit rat kidney AR by an in vitro spectrophotometric assay. Results showed that compounds containing piperidine at the C-2 position of thiazole ring showed better inhibitory activity than thiazole compounds having 4-chlorobenzylsulfanyl at the same position.

  DOI：

  10.1007/s00044-007-9008-9

文献信息

• Some new thiazolyl thiazolidinedione derivatives as aldose reductase inhibitors
  作者：Oya Bozdağ-Dündar、Net Daş Evcimen、Meltem Ceylan-Ünlüsoy、Rahmiye Ertan、Mutlu Sarıkaya

  DOI：10.1007/s00044-007-9008-9

  日期：2008.1

  In diabetes, increased flux through the polyol pathway has been implicated in the development of diabetic complications such as cataract, retinopathy, neuropathy, and nephropathy. Aldose reductase (AR) appears to be the key factor in the reduction of glucose to sorbitol. Aldose reductase inhibitors have been found to prevent sorbitol accumulation in tissues. A series of thiazolyl-2,4-thiazolidinediones was prepared by Knoevenagel reaction of substituted benzyl-2,4-thiazolidinediones with chlorothiazolecarbaldehydes and were evaluated for their ability to inhibit rat kidney AR by an in vitro spectrophotometric assay. Results showed that compounds containing piperidine at the C-2 position of thiazole ring showed better inhibitory activity than thiazole compounds having 4-chlorobenzylsulfanyl at the same position.