5-(3-Methoxybenzyl)thiazolidine-2,4-dione | 503826-56-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 5-(3-Methoxybenzyl)thiazolidine-2,4-dione
• 英文别名: 5-[(3-Methoxyphenyl)methyl]-1,3-thiazolidine-2,4-dione
• CAS: 503826-56-0
• 化学式: C₁₁H₁₁NO₃S
• 分子量: 237.279
• InChiKey: FLKJGTGDTWYQNY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 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-(3-Methoxybenzyl)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 [5-(3-Methoxy-benzyl)-2,4-dioxo-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：

  (5Z)-5-(3-甲氧基亚苄基)噻唑烷-2,4-二酮 在 吡啶 、 锂硼氢 作用下， 以 四氢呋喃 为溶剂， 以40%的产率得到5-(3-Methoxybenzyl)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

• Novel ligands for the hisb10 zn2+ sites of the r-state insulin hexamer
  申请人：——

  公开号：US20030229120A1

  公开（公告）日：2003-12-11

  Novel ligands for the HisB10 Zn 2+ sites of the R-state insulin hexamer that are capable of prolonging the action of insulin preparations are disclosed.

  揭示了能够延长胰岛素制剂作用的R-态胰岛素六聚体的HisB10 Zn2+位点的新配体。
• [EN] PHAMACEUTICAL PREPARATIONS COMPRISING INSULIN<br/>[FR] PREPARATIONS PHARMACEUTIQUES CONTENANT DE L'INSULINE
  申请人：NOVO NORDISK AS

  公开号：WO2006005683A1

  公开（公告）日：2006-01-19

  Novel preparations comprising ligands for the HisB10 Zn2+ sites of the R-state insulin hexamer wherein the ligand is extended by protamine that are capable of prolonging the ac­tion of insulin preparations.

  新型制剂包括配体，用于R-态胰岛素六聚体的HisB10 Zn2+位点，其中配体通过精氨酸延长，能够延长胰岛素制剂的作用。
• Stabilised insulin compositions
  申请人：Kaarsholm Christian Niels

  公开号：US20050065066A1

  公开（公告）日：2005-03-24

  The present invention provides pharmaceutical compositions comprising insulin and novel ligands for the His B10 Zn 2+ sites of the R-state insulin hexamer. The resulting preparations have improved physical and chemical stability.

  本发明提供了包含胰岛素和新型配体的药物组合物，用于R-态胰岛素六聚体的His B10 Zn2+位点。由此制备的药物具有改善的物理和化学稳定性。
• [EN] PHARMACEUTICAL PREPARATIONS COMPRISING ACID-STABILISED INSULIN<br/>[FR] PREPARATIONS PHARMACEUTIQUES CONTENANT DE L'INSULINE STABILISEE D'UN POINT DE VUE ACIDE
  申请人：NOVO NORDISK AS

  公开号：WO2004080480A1

  公开（公告）日：2004-09-23

  Novel ligands for the HisB10 Zn2+ sites of the R-state insulin hexamer that are capable of prolonging the action of insulin preparations are disclosed.

  揭示了能够延长胰岛素制剂作用的R态胰岛素六聚体的HisB10 Zn2+位点的新配体。
• Pharmaceutical preparations comprising acid-stabilised insulin
  申请人：Ostergaard Soren

  公开号：US20060069013A1

  公开（公告）日：2006-03-30

  Novel ligands for the HisB10 Zn 2+ sites of the R-state insulin hexamer that are capable of prolonging the action of insulin preparations are disclosed.

  本发明揭示了能够延长胰岛素制剂作用的R态胰岛素六聚体的HisB10 Zn2+位点的新型配体。