(Z)-5-(4-methoxybenzylidene)thiazolidine-2,4-dione | 6320-51-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (Z)-5-(4-methoxybenzylidene)thiazolidine-2,4-dione
• 英文别名: 5-(4-methoxy-benzylidene)-thiazolidine-2,4-dione；5-(4-Methoxybenzylidene)-1,3-thiazolidine-2,4-dione；(5Z)-5-[(4-methoxyphenyl)methylidene]-1,3-thiazolidine-2,4-dione
• CAS: 6320-51-0
• 化学式: C₁₁H₉NO₃S
• 分子量: 235.263
• InChiKey: VRUKGUBMRBLJJW-TWGQIWQCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  80.7
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 危险性防范说明：
  P261,P264,P270,P271,P280,P301+P312,P302+P352,P304+P340,P305+P351+P338,P330,P332+P313,P337+P313,P362,P403+P233,P405,P501
• 危险性描述：
  H302,H315,H319,H335

反应信息

• 作为反应物：
  描述：

  (Z)-5-(4-methoxybenzylidene)thiazolidine-2,4-dione 在 吡啶 、 盐酸 、 锂硼氢 、 potassium carbonate 、 溶剂黄146 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 25.5h， 生成 2-(5-(4-methoxybenzyl)-2,4-dioxothiazolidin-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：

  对氟苯甲醛 在 哌啶 、 potassium tert-butylate 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 12.0h， 生成 (Z)-5-(4-methoxybenzylidene)thiazolidine-2,4-dione
  参考文献：
  名称：

  Structure–activity requirements for the antiproliferative effect of troglitazone derivatives mediated by depletion of intracellular calcium

  摘要：

  Depletion of calcium from the endoplasmic reticulum has shown to affect protein synthesis and cell proliferation. The anticancer effect of troglitazone was reported to be mediated by depletion of intracellular calcium stores resulting in inhibition of translation initiation. The unsaturated form of troglitazone displays similar anticancer properties in vitro. In this letter, we report our findings on the minimum structural requirements for both compounds to retain their calcium release and antiproliferative activities. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.02.087

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。
• Diversity-Oriented Synthesis of Spiropyrrolo[1,2-<i>a</i>]isoquinoline Derivatives via Diastereoselective and Regiodivergent Three-Component 1,3-Dipolar Cycloaddition Reactions:<i>In Vitro</i>and<i>in Vivo</i>Evaluation of the Antidiabetic Activity of Rhodanine Analogues
  作者：Amani Toumi、Sarra Boudriga、Khaled Hamden、Ismail Daoud、Moheddine Askri、Armand Soldera、Jean-Francois Lohier、Carsten Strohmann、Lukas Brieger、Michael Knorr

  DOI：10.1021/acs.joc.1c01544

  日期：2021.10.1

  endured retro-1,3-dipolar cycloaddition/recycloaddition reactions under thermal or catalytic conditions to regenerate the corresponding regioisomeric counterpart. In addition, DFT calculations were performed at the M062X/6-31++g(d,p) level of theory to unravel the origin of the reversal of regioselectivity and endo-stereoselectivity of the title 1,3-dipolar cycloaddition reactions. Upon treatment of Isatin

  开发了一种有效的非对映选择性路线，通过( Z )-5-亚芳基-1,3的一锅三组分 [3 + 2] 环加成反应获得新型螺吡咯[1,2- a ] 异喹啉-羟吲哚骨架-噻唑烷-2,4-二酮、靛红衍生物和 1,2,3,4-四氢异喹啉 (THIQ)。有趣的是，该反应的区域选择性既取决于温度，也取决于溶剂，允许以优异的产率合成两种区域异构的内-二螺吡咯并[2,1- a ]异喹啉并吲哚。前所未有地，每个异构体二螺吡咯并[2,1- a ]异喹啉并吲哚都经受了逆1,3-偶极环加成/再环加成反应在热或催化条件下再生相应的区域异构体对应物。此外，在 M062X/6-31++g(d,p) 理论水平上进行了 DFT 计算，以解开标题 1,3-偶极环加成反应的区域选择性和内立体选择性逆转的起源。在用 ( Z )-4-arylidene-5-thioxo-thiazolidin-2-ones 作为偶极体处理靛红、THIQ
• Phosphoryl Chloride Mediated Synthesis of 5-Arylidene-2,4-Thiazolidinediones Derivatives via Aromatic Bisulfite Adducts
  作者：Sandeep Mohanty、Sandeep G、Arun Karmakar

  DOI：10.2174/15701786113106660081

  日期：2014.2

  The carbon-carbon bond formation by the condensation of bisulfite adduct of aromatic aldehydes with thiazolidine-2, 4-dione to furnish 5-arylidene-2,4-thiazolidinedione’s has been investigated. This novel methodology was applied to convert substituted aryl bisulfite adducts to corresponding 5-arylidene-2,4-thiazolidinedione’s with POCl3 in less-polar solvents such as toluene, chlorobenzene and o-xylene. 5-(4-methoxybenzylidene)thiazolidine-2,4-dione and 5-(4-ethoxybenzylidene)thiazolidine-2,4-dione were obtained in good yields.

  通过芳香醛的亚硫酸氢盐加合物与噻唑烷-2,4-二酮的缩合反应形成碳-碳键以制备5-芳亚甲基-2,4-噻唑烷二酮的研究已经开展。这一新颖方法被应用于将取代的芳基亚硫酸氢盐加合物在较非极性溶剂如甲苯、氯苯和邻二甲苯中，使用POCl3转化为相应的5-芳亚甲基-2,4-噻唑烷二酮。5-(4-甲氧基苄叉基)噻唑烷-2,4-二酮和5-(4-乙氧基苄叉基)噻唑烷-2,4-二酮以良好产率获得。

表征谱图