5-[1-(4-Dimethylamino-phenyl)-meth-(Z)-ylidene]-3-(4-methyl-benzyl)-thiazolidine-2,4-dione

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 5-[1-(4-Dimethylamino-phenyl)-meth-(Z)-ylidene]-3-(4-methyl-benzyl)-thiazolidine-2,4-dione
• 英文别名: (5Z)-5-[4-(dimethylamino)benzylidene]-3-(4-methylbenzyl)-1,3-thiazolidine-2,4-dione；(5Z)-5-[[4-(dimethylamino)phenyl]methylidene]-3-[(4-methylphenyl)methyl]-1,3-thiazolidine-2,4-dione
• 化学式: C₂₀H₂₀N₂O₂S
• 分子量: 352.457
• InChiKey: WFNLNMITCCCODL-PDGQHHTCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  65.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-[(4-甲基苯基)甲基]-1,3-噻唑烷-2,4-二酮 、 2-氰基-3-[4-(二甲基氨基)苯基]丙烯酸乙酯 在 哌啶 作用下， 以 乙醇 为溶剂， 生成 5-[1-(4-Dimethylamino-phenyl)-meth-(Z)-ylidene]-3-(4-methyl-benzyl)-thiazolidine-2,4-dione
  参考文献：
  名称：

  Synthesis, biological evaluation and molecular modeling studies of arylidene-thiazolidinediones with potential hypoglycemic and hypolipidemic activities

  摘要：

  New arylidene-thiazolidinediones (ATZDs) were synthesized and evaluated in the alloxan-induced hyperglycemia mice model. The molecular target taken into consideration is the nuclear PPAR-gamma whose crystallographic structure is available on the PDB database as 2PRG. Thus the hypoglycemic and hypolipidemic activities of compounds were compared with the result of their docking after removal of the co-crystallized ligand present in the 2PRG structure. Molecular modeling studies were carried out using the Autodock 3.0.5 and ADT 1.1 programs. (c) 2007 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2007.02.015

文献信息

• Synthesis and Biological Activity of Novel Acridinylidene and Benzylidene thiazolidinediones
  作者：R.H. Mourão、T.G. Silva、A.L.M. Soares、E.S. Vieira、J.N. Santos、M.C.A. Lima、V.L.M. Lima、S.L. Galdino、J. Barbe、I.R. Pitta

  DOI：10.1016/j.ejmech.2005.06.002

  日期：2005.11

  A novel set of acridinylidene thiazolidinediones and benzylidene thiazolidinediones was synthesized by nucleophilic addition of cyanoacrylates. Some of these compounds were evaluated for their glucose lowering capability and their effects on the triglyceride level in alloxan diabetic mice. (c) 2005 Elsevier SAS. All rights reserved.
• [EN] THIAZOLIDINEDIONE COMPOUNDS WITH HYPOGLYCEMIC PROPERTIES<br/>[FR] COMPOSES DE THIAZOLIDINE POSSEDANT DES PROPRIETES HYPOGLYCEMIQUES
  申请人：CONSELHO NACIONAL CNPQ

  公开号：WO2004089276A2

  公开（公告）日：2004-10-21

  The compounds invented constitute a new series of thiazolidine derivatives, 5-benzylidene-3-(4-mehyl-benzyl)-thiazolidine-2,4-diones (ATDZs) substituted in benzylidene ring and 5-(1H-indol-3-yl-methylene)-3-(4-methyl-benzyl)-thiazolidine-2,4-dione (ITDZ); all have pharmacological uses and anti-diabetic effects. These, therefore, represent a new series of anti-diabetic agents which act on the nuclear receptor hormone PPARg, exhibiting hypoglycemic properties and potential for therapeutic use as anti-diabetes drugs.
• Synthesis, biological evaluation and molecular modeling studies of arylidene-thiazolidinediones with potential hypoglycemic and hypolipidemic activities
  作者：Lúcia Fernanda C. da Costa Leite、Rosa Helena Veras Mourão、Maria do Carmo Alves de Lima、Suely Lins Galdino、Marcelo Zaldini Hernandes、Francisco de Assis Rocha Neves、Stéphanie Vidal、Jacques Barbe、Ivan da Rocha Pitta

  DOI：10.1016/j.ejmech.2007.02.015

  日期：2007.10

  New arylidene-thiazolidinediones (ATZDs) were synthesized and evaluated in the alloxan-induced hyperglycemia mice model. The molecular target taken into consideration is the nuclear PPAR-gamma whose crystallographic structure is available on the PDB database as 2PRG. Thus the hypoglycemic and hypolipidemic activities of compounds were compared with the result of their docking after removal of the co-crystallized ligand present in the 2PRG structure. Molecular modeling studies were carried out using the Autodock 3.0.5 and ADT 1.1 programs. (c) 2007 Elsevier Masson SAS. All rights reserved.