(2R)-2-(4-methoxyphenyl)-3-[2-[(2R)-2-(4-methoxyphenyl)-4-oxo-1,3-thiazolidin-3-yl]ethyl]-1,3-thiazolidin-4-one

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (2R)-2-(4-methoxyphenyl)-3-[2-[(2R)-2-(4-methoxyphenyl)-4-oxo-1,3-thiazolidin-3-yl]ethyl]-1,3-thiazolidin-4-one
• 化学式: C₂₂H₂₄N₂O₄S₂
• 分子量: 444.576
• InChiKey: MEIHFWBAEBWTRG-FGZHOGPDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  110
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  N1,N2双[(4-甲氧基苯基)亚甲基]-1,2-乙二胺 、 巯基乙酸 以56%的产率得到(2R)-2-(4-methoxyphenyl)-3-[2-[(2R)-2-(4-methoxyphenyl)-4-oxo-1,3-thiazolidin-3-yl]ethyl]-1,3-thiazolidin-4-one
  参考文献：
  名称：

  3，3'-（1,2-乙二基）-双[2-芳基-4-噻唑烷酮]手性化合物的合成及抗炎，镇痛作用。第10部分

  摘要：

  在此说明中，新系列的2R，2'R / 2S，2'S和2R，2'S-间消旋3,3'-（1,2-乙二基）-双[2-芳基-描述了4-噻唑烷酮。通过角叉菜胶诱导的爪水肿试验研究了抗炎活性，并且通过乙酸扭结法和热板试验研究了大鼠的镇痛活性。所有化合物均显示出致溃疡作用和急性毒性，远低于消炎痛和苯基丁a。中观异构体（b）显示出比相应的外消旋体（a）更好的药理特性。在药理学特征上，立体异构碳上的芳基的甲氧基取代模式通常是最有利的。

  DOI：

  10.1016/s0960-894x(01)00476-0

文献信息

• Modeling and biological evaluation of 3,3′-(1,2-ethanediyl)bis[2-(4-methoxyphenyl)-thiazolidin-4-one], a new synthetic cyclooxygenase-2 inhibitor
  作者：Rosaria Ottaná、Emanuela Mazzon、Laura Dugo、Francesca Monforte、Rosanna Maccari、Lidia Sautebin、Grazia De Luca、Maria Gabriella Vigorita、Stefano Alcaro、Francesco Ortuso、Achille P Caputi、Salvatore Cuzzocrea

  DOI：10.1016/s0014-2999(02)01888-5

  日期：2002.7

  Within the series of chiral 3,3'-(1,2-ethanediyl)bis[2-arylthiazolidin-4-ones], the 3,4-dimethoxyphenyl substituted derivative was found in the primary anti-inflammatory screening to be endowed with superior in vivo properties and good safety profile. Such a lead compound was modified by eliminating 3-methoxy group while retaining 4-methoxy group on the aryl rings at 2 and 2' stereogenic carbons. The 2R,2'S-meso isomer (VIG3b) of the resulting bisthiazolidinone has been widely investigated. The inhibitory effects on cyclo-oxygenase-1 and cyclo-oxygenase-2 isoenzymes were measured in a human whole blood assay. VIG3b was almost 50 times more selective on the inducible isoform. The cyclo-oxygenase-2 preferential selectivity has been confirmed by modeling VIG3b into the cyclo-oxygenase-1 and cyclo-oxygenase-2 active sites. furthermore, VIG3b was assayed in the experimental model of carrageenan-induced lung injury by evaluating its ability to inhibit: (1) fluid accumulation in the pleural cavity, (2) neutrophil infiltration, (3) prostaglandin E-2 production and (4) lung injury. VIG3b exhibited interesting activity in all these tests. (C) 2002 Elsevier Science B.V. All rights reserved.