(5E)-5-[(4-chlorophenyl)methylidene]-2-(1,3-thiazol-2-ylimino)-1,3-thiazolidin-4-one

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (5E)-5-[(4-chlorophenyl)methylidene]-2-(1,3-thiazol-2-ylimino)-1,3-thiazolidin-4-one
• 化学式: C₁₃H₈ClN₃OS₂
• 分子量: 321.811
• InChiKey: ABZKRIMFSCMKFI-JXMROGBWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  108
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-氯苯甲醛 、 2-(thiazol-2-ylimino)thiazolidin-4-one 在 sodium acetate 、 溶剂黄146 作用下， 反应 4.0h， 生成 (5E)-5-[(4-chlorophenyl)methylidene]-2-(1,3-thiazol-2-ylimino)-1,3-thiazolidin-4-one
  参考文献：
  名称：

  Computer-Aided Discovery of Anti-Inflammatory Thiazolidinones with Dual Cyclooxygenase/Lipoxygenase Inhibition

  摘要：

  New anti-inflammatory agents possessing dual cyclooxygenase/lipoxygenase (COX/LOX) inhibition were discovered by computer-aided prediction of biological activity for 573 virtually designed chemical compounds. Prediction of biological activity was performed by PASS, and prediction results were analyzed with PharmaExpert software. Nine 2-(thiazole-2-ylamino)-5-phenylidene-4-thiazolidinone derivatives differing by the phenyl group substitution were selected for synthesis and experimental testing as potential COX/ LOX inhibitors. Eight tested compounds exhibited anti-inflammatory activity in the carrageenin-induced paw edema. It was shown that seven tested compounds (77.8%) were LOX inhibitors, seven compounds were COX inhibitors (77.8%), and six tested compounds (66.7%) were dual COX/LOX inhibitors. Analysis of lipophilicity of the compounds showed a negative correlation with inhibition of edema formation. The binding modes of the most active compounds of this series (2-(thiazole-2-ylamino)-5-(m-chlorophenylidene)-4-thiazolidinone for COX-1 and COX-2, and 2-(thiazole-2-ylamino)-5-(m-nitrophenylidene)-4-thiazolidinone for 15-LOX) were proposed on the basis of docking studies.

  DOI：

  10.1021/jm701496h

文献信息

• Computer-Aided Discovery of Anti-Inflammatory Thiazolidinones with Dual Cyclooxygenase/Lipoxygenase Inhibition
  作者：Athina A. Geronikaki、Alexey A. Lagunin、Dimitra I. Hadjipavlou-Litina、Phaedra T. Eleftheriou、Dmitrii A. Filimonov、Vladimir V. Poroikov、Intekhab Alam、Anil K. Saxena

  DOI：10.1021/jm701496h

  日期：2008.3.1

  New anti-inflammatory agents possessing dual cyclooxygenase/lipoxygenase (COX/LOX) inhibition were discovered by computer-aided prediction of biological activity for 573 virtually designed chemical compounds. Prediction of biological activity was performed by PASS, and prediction results were analyzed with PharmaExpert software. Nine 2-(thiazole-2-ylamino)-5-phenylidene-4-thiazolidinone derivatives differing by the phenyl group substitution were selected for synthesis and experimental testing as potential COX/ LOX inhibitors. Eight tested compounds exhibited anti-inflammatory activity in the carrageenin-induced paw edema. It was shown that seven tested compounds (77.8%) were LOX inhibitors, seven compounds were COX inhibitors (77.8%), and six tested compounds (66.7%) were dual COX/LOX inhibitors. Analysis of lipophilicity of the compounds showed a negative correlation with inhibition of edema formation. The binding modes of the most active compounds of this series (2-(thiazole-2-ylamino)-5-(m-chlorophenylidene)-4-thiazolidinone for COX-1 and COX-2, and 2-(thiazole-2-ylamino)-5-(m-nitrophenylidene)-4-thiazolidinone for 15-LOX) were proposed on the basis of docking studies.