5-(3-Phenoxy-benzyl)-thiazolidine-2,4-dione | 262844-57-5

• 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-(3-Phenoxy-benzyl)-thiazolidine-2,4-dione
• 英文别名: 5-(3-Phenoxybenzyl)-1,3-thiazolane-2,4-dione；5-[(3-phenoxyphenyl)methyl]-1,3-thiazolidine-2,4-dione
• CAS: 262844-57-5
• 化学式: C₁₆H₁₃NO₃S
• 分子量: 299.35
• InChiKey: CEZZBCMZOCJIEY-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-(3-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-(3-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-(3-Phenoxybenzylidene)thiazolidine-2,4-dione 在 吡啶 、 锂硼氢 作用下， 以 四氢呋喃 为溶剂， 以43%的产率得到5-(3-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

• [EN] THIAZOLIDINE DERIVATIVES FOR THE TREATMENT AND PREVENTION OF METABOLIC BONE DISORDERS<br/>[FR] DERIVES DE THIAZOLIDINE UTILES POUR LE TRAITEMENT ET LA PREVENTION DE TROUBLES METABOLIQUES DES OS
  申请人：ROCHE DIAGNOSTICS GMBH

  公开号：WO2000018746A1

  公开（公告）日：2000-04-06

  The object of the present invention are compounds of general formula (I), in which: m signifies a number between 0-8; q signifies a number between 0-8; A signifies a single or double bond; R1 signifies hydrogen or, when X and Z are oxygen, also -(CH2)-COR4 with a =0-6; R2, R3 signify hydrogen or lower alkyl, whereby R2 and R3 can be the same or different and, when m signifies 2-8, R2 and R3 in the group CR2=CR3 can have various significances within the following sequence; R4 signifies hydroxyl, lower alkoxy or the NR1R2 residue, whereby R1 and R2 can be the same or different; X signifies oxygen or imino; Z signifies oxygen, sulfur or imino; W signifies an optionally mono- or polysubstituted saturated or unsaturated mono-, bi- or tricycle which can contain one or more hetero atoms, as well as their physiologically compatible salts, esters, optically active forms, racemates, tautomers, as well as derivatives which can be metabolized in vivo to compounds of general formula (I), as well as the use of these compounds for the production of medicaments for the prophylaxis or therapy of metabolic bone disorders.
• 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.