5-(4-Phenoxy-benzyl)-thiazolidine-2,4-dione | 85002-17-1

• 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: 5-(4-Phenoxy-benzyl)-thiazolidine-2,4-dione
• 英文别名: 5-[(4-Phenoxyphenyl)methyl]-1,3-thiazolidine-2,4-dione
• CAS: 85002-17-1
• 化学式: C₁₆H₁₃NO₃S
• 分子量: 299.35
• InChiKey: HVQBTDHBNQXHKK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  80.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-(4-Phenoxy-benzyl)-thiazolidine-2,4-dione 在 盐酸 、 potassium carbonate 、 溶剂黄146 作用下， 以 丙酮 为溶剂， 反应 25.5h， 生成 [2,4-Dioxo-5-(4-phenoxy-benzyl)-thiazolidin-3-yl]-acetic acid
  参考文献：
  名称：

  In vitro aldose reductase inhibitory activity of 5-benzyl-2,4-thiazolidinediones

  摘要：

  Several 5-benzyl-2,4-thiazolidinediones (5-7) were synthesised and tested as in vitro aldose reductase (ALR2) inhibitors. Most of them particularly N-unsubstituted 5-benzyl-2,4-thiazolidinediones 5 and (5-benzyl-2,4-dioxothiazolidin-3-yl)acetic acids 7, displayed moderate to high inhibitory activity levels. In detail, the insertion of an acetic chain on N-3 significantly enhanced ALR2 inhibitory potency, leading to acids 7 which proved to be the most effective among the tested compounds. In addition, in N-unsubstituted derivatives 5 the presence of an additional aromatic ring on the 5-benzyl moiety was generally beneficial. In fact, the ALR2 inhibition results of compounds 5-7, compared to those of the previously assayed corresponding 5-arylidene-2,4-thiazolidinediones, indicated that N-unsubstituted derivatives 5b, c and d, which bore an additional aromatic group in the para position of the 5-benzyl residue were significantly more effective than their 5-arylidene counterparts; in all other cases, the saturation of the exocyclic double bond C=C in 5 brought about a moderate decrease in activity. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.08.056
• 作为产物：
  描述：

  5-(4-Phenoxy-benzylidene)-thiazolidine-2,4-dione 在 吡啶 、 锂硼氢 作用下， 以 四氢呋喃 为溶剂， 以42%的产率得到5-(4-Phenoxy-benzyl)-thiazolidine-2,4-dione
  参考文献：
  名称：

  In vitro aldose reductase inhibitory activity of 5-benzyl-2,4-thiazolidinediones

  摘要：

  Several 5-benzyl-2,4-thiazolidinediones (5-7) were synthesised and tested as in vitro aldose reductase (ALR2) inhibitors. Most of them particularly N-unsubstituted 5-benzyl-2,4-thiazolidinediones 5 and (5-benzyl-2,4-dioxothiazolidin-3-yl)acetic acids 7, displayed moderate to high inhibitory activity levels. In detail, the insertion of an acetic chain on N-3 significantly enhanced ALR2 inhibitory potency, leading to acids 7 which proved to be the most effective among the tested compounds. In addition, in N-unsubstituted derivatives 5 the presence of an additional aromatic ring on the 5-benzyl moiety was generally beneficial. In fact, the ALR2 inhibition results of compounds 5-7, compared to those of the previously assayed corresponding 5-arylidene-2,4-thiazolidinediones, indicated that N-unsubstituted derivatives 5b, c and d, which bore an additional aromatic group in the para position of the 5-benzyl residue were significantly more effective than their 5-arylidene counterparts; in all other cases, the saturation of the exocyclic double bond C=C in 5 brought about a moderate decrease in activity. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.08.056

文献信息

• Studies on antidiabetic agents. II. Synthesis of 5-(4-(1-methylcyclohexylmethoxy)-benzyl)thiazolidine-2,4-dione (ADD-3878) and its derivatives.
  作者：TAKASHI SOHDA、KATSUTOSHI MIZUNO、EIKO IMAMIYA、YASUO SUGIYAMA、TAKESHI FUJITA、YUTAKA KAWAMATSU

  DOI：10.1248/cpb.30.3580

  日期：——

  More than 100 5-substituted thiazolidine-2, 4-diones were prepared and their hypoglycemic and hypolipidemic activities were evaluated with genetically obese and diabetic mice, yellow KK. The structure-activity relationship study showed that the 5-(4-oxybenzyl) moiety is essential for substantial activity. Among these compounds, 5-(4-cyclohexylmethoxy) benzylthiazolidine-2, 4-dione (47), 5-[4-(1-methylcyclohexylmethoxy) benzyl]-thiazolidine-2, 4-dione (49, ADD-3878) and 5-4-[2-(3-pyridyl) ethoxy] benzyl} thiazolidine-2, 4-dione (59) exhibited the most favorable properties in terms of activity and toxicity.

  合成了100多种5-取代的噻唑烷-2,4-二酮类化合物，并通过遗传性肥胖和糖尿病小鼠（KK黄色小鼠）评估了它们的降血糖和降血脂活性。结构-活性关系研究表明，5-(4-羟基苄基)部分对于显著活性是必要的。在这些化合物中，5-(4-环己基甲氧基)苄基噻唑烷-2,4-二酮（47）、5-[4-(1-甲基环己基甲氧基)苄基]-噻唑烷-2,4-二酮（49，ADD-3878）和5-4-[2-(3-吡啶基)乙氧基]苄基}噻唑烷-2,4-二酮（59）在活性和毒性方面表现出最佳特性。
• SOHDA, TAKASHI;MIZUNO, KATSUTOSHI;IMAMIYA, EIKO;SUGIYAMA, YASUO;FUJITATAK+, CHEM. AND PHARM. BULL., 1982, 30, N 10, 3580-3600
  作者：SOHDA, TAKASHI、MIZUNO, KATSUTOSHI、IMAMIYA, EIKO、SUGIYAMA, YASUO、FUJITATAK+

  DOI：——

  日期：——
• In vitro aldose reductase inhibitory activity of 5-benzyl-2,4-thiazolidinediones
  作者：Dietmar Rakowitz、Rosanna Maccari、Rosaria Ottanà、Maria Gabriella Vigorita

  DOI：10.1016/j.bmc.2005.08.056

  日期：2006.1

  Several 5-benzyl-2,4-thiazolidinediones (5-7) were synthesised and tested as in vitro aldose reductase (ALR2) inhibitors. Most of them particularly N-unsubstituted 5-benzyl-2,4-thiazolidinediones 5 and (5-benzyl-2,4-dioxothiazolidin-3-yl)acetic acids 7, displayed moderate to high inhibitory activity levels. In detail, the insertion of an acetic chain on N-3 significantly enhanced ALR2 inhibitory potency, leading to acids 7 which proved to be the most effective among the tested compounds. In addition, in N-unsubstituted derivatives 5 the presence of an additional aromatic ring on the 5-benzyl moiety was generally beneficial. In fact, the ALR2 inhibition results of compounds 5-7, compared to those of the previously assayed corresponding 5-arylidene-2,4-thiazolidinediones, indicated that N-unsubstituted derivatives 5b, c and d, which bore an additional aromatic group in the para position of the 5-benzyl residue were significantly more effective than their 5-arylidene counterparts; in all other cases, the saturation of the exocyclic double bond C=C in 5 brought about a moderate decrease in activity. (c) 2005 Elsevier Ltd. All rights reserved.