5-benzylidene-2,4-thiazolidinedione | 3774-99-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: 5-benzylidene-2,4-thiazolidinedione
• 英文别名: 5-benzylidenethiazolidine-2,4-dione；5-Benzyliden-thiazolidindion-(2,4)；5-Benzyliden-thiazolidin-2,4-dion；5-Benzyliden-2,4-thiazolidindion；5-(benzylidene)-1,3-thiazolidine-2,4-dione；Benzylidene thiazolidinedione；5-benzylidene-1,3-thiazolidine-2,4-dione
• CAS: 3774-99-0
• 化学式: C₁₀H₇NO₂S
• 分子量: 205.237
• InChiKey: SGIZECXZFLAGBW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  71.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-benzylidene-2,4-thiazolidinedione 在 potassium hydroxide 作用下， 以 乙醇 为溶剂， 以80%的产率得到5-Benzylidene-2,4-dioxothiazolidine potassium salt
  参考文献：
  名称：

  Permuted 2,4-thiazolidinedione (TZD) analogs as GLUT inhibitors and their in-vitro evaluation in leukemic cells

  摘要：

  Cancer is a heterogeneous disease, and its treatment requires the identification of new ways to thwart tumor cells. Amongst such emerging targets are glucose transporters (GLUTs, SLC2 family), which are overexpressed by almost all types of cancer cells; their inhibition provides a strategy to disrupt tumor metabolism selectively, leading to antitumor effects. Here, novel thiazolidinedione (TZD) derivatives were designed, synthesized, characterized, and evaluated for their GLUT1, GLUT4, and GLUT5 inhibitory potential, followed by in-vitro cytotoxicity determination in leukemic cell lines. Compounds G5, G16, and G17 inhibited GLUT1, with IC50, values of 5.4 +/- 1.3, 26.6 +/- 1.8, and 12.6 +/- 1.2 mu M, respectively. G17 was specific for GLUT1, G16 inhibited GLUT4 (IC50 = 21.6 +/- 4.5 mu M) comparably but did not affect GLUT5. The most active compound, G5, inhibited all three GLUT types, with GLUT4 IC50 = 9.5 +/- 2.8 mu M, and GLUT5 IC50 = 34.5 +/- 2.4 mu M. Docking G5, G16, and G17 to the inward- and outward-facing structural models of GLUT1 predicted ligand binding affinities consistent with the kinetic inhibition data and implicated E380 and W388 of GLUT1 vs. their substitutions in GLUT5 (A388 and A396, respectively) in inhibitor preference for GLUT1. G5 inhibited the proliferation of leukemia CEM cells at low micromolar range (IC50 = 13.4 mu M) while being safer for normal blood cells. Investigation of CEM cell cycle progression after treatment with G5 showed that cells accumulated in the G2/M phase. Flow cytometric apoptosis studies revealed that compound G5 induced both early and late-stage apoptosis in CEM cells.

  DOI：

  10.1016/j.ejps.2020.105512
• 作为产物：
  描述：

  苯甲醛吖嗪 在 盐酸 、 一水合肼 作用下， 以 乙醇 、 溶剂黄146 为溶剂， 反应 23.0h， 生成 5-benzylidene-2,4-thiazolidinedione
  参考文献：
  名称：

  Thiocyanoacetate. III. The Synthesis of 2-Hydrazono-4-thiazolidinone Derivatives

  摘要：

  DOI：

  10.1246/bcsj.45.952

文献信息

• Ternary condensation of Biginelli thiones, chloroacetic acid, and aldehydes as an effective approach towards thiazolo[3,2-a]pyrimidines and 5-arylidenethiazolidine-2,4-diones
  作者：Iryna O. Lebedyeva、Mykhaylo V. Povstyanoy、Aleksey B. Ryabitskii、Vyacheslav M. Povstyanoy

  DOI：10.1002/jhet.323

  日期：——

  the process of ethyl 6‐methyl‐4‐aryl‐2‐thioxo‐1,2,3,4‐tetrahydropyrimidine‐5‐carboxylates condensation with aryl aldehydes and chloroacetic acid the unexpected formation of 5‐arylidenethiazolidine‐2,4‐diones was determined in high yields as the reaction time was increased to 20 h. The latter represent the products of destructive hydrolyzes of ethyl 2‐benzylidene‐7‐methyl‐3‐oxo‐5‐aryl‐2,3‐dihydro‐5H‐[1

  在6-甲基-4-芳基-2-硫代氧杂1,2,3,4-四氢嘧啶-5-羧酸乙酯与芳基醛和氯乙酸缩合的过程中，意外地形成了5-芳基萘并噻唑烷-2,4-二酮随着反应时间增加到20小时，可以高产率确定Sn。后者代表的2-亚苄基-7-甲基-3-氧代- 5-芳基-2,3-二氢-5-破坏性水解的产物ħ - [1,3]噻唑并[3,2-一个]嘧啶6-羧酸盐已通过独立合成证明。J.杂环化​​学。（2010）。
• Microwave Assisted Urea-Acetic Acid Catalyzed Knoevenagel Condensation of Ethyl Cyanoacetate and 1,3-Thiazolidine-2,4-dione with Aromatic Aldehydes under Solvent Free Condition
  作者：Pravin. T. Tryambake

  DOI：10.14233/ajchem.2017.20695

  日期：——

  conditions [17], microwave irradiation [18], piperidine in ethanol [19a], piperidinium acetate in toluene under reflux conditions [19b], piperidinium acetate in DMF under microwave irradiation [20], glycine and sodium carbonate in H2O under reflux conditions [21], grinding with ammonium acetate in the absence of solvents [22], alum in H2O [23], Baker’s yeast [24], KF-Al2O3 under microwave irradiation [25]

  Knoevenagel缩合反应是有机化学中形成碳碳双键的重要反应。其中一种产物α-氰基肉桂酸乙酯是合成不同药学上重要的有机化合物的重要中间体，也用于造纸、染料、纤维、塑料等[1]。4-噻唑烷酮的其他产品 5-亚芳基衍生物在制药工业中广为人知，并已显示出广泛的生物活性，包括抗炎 [2a]、抗菌 [2b]、抗病毒 [2c]、抗微生物 [2d]、抗真菌 [ 2e] 并具有醛糖还原酶抑制剂 [2f]、抗糖尿病活性 [2g-k]。已经开发了许多用于芳醛和氰基乙酸乙酯的 Knoevengel 缩合的合成策略。
• Solid acid TS-1 catalyst: an efficient catalyst in Knoevenagel condensation for the synthesis of 5-arylidene-2,4-thiazolidinediones/Rhodanines in aqueous medium
  作者：Sachin P. Gadekar、Sudarshan S. Dipake、Suresh T. Gaikwad、Machhindra K. Lande

  DOI：10.1007/s11164-018-3570-2

  日期：2018.12

  catalytic activity of the catalyst was tested for Knoevenagel condensation reaction. The condensation of active ethylene 2,4-thiazolidinedione with substituted aryl aldehydes under aqueous medium at 90 °C afforded the corresponding product in excellent yield up to 92% within 30 min. The present method offers several advantages over the reported methods such as easy separation of catalyst, simple work-up procedure

  摘要 采用水热处理将钛（IV）阳离子掺入硅酸盐-1骨架中，制备了TS-1沸石，用于在水介质中合成5-芳基-2,4-噻唑烷二酮/若丹宁，并通过XRD，EDX，BET表征，FT-IR和SEM技术。测试了该催化剂对于Knoevenagel缩合反应的催化活性。活性乙烯2,4-噻唑烷二酮与取代的芳基醛在水性介质下于90°C下缩合，可在30分钟内以高达92％的优异收率得到相应的产物。本方法相对于所报道的方法具有多个优点，例如容易分离催化剂，简单的后处理程序以及所需产物的优异产率。此外，催化剂可以重复使用而活性没有明显损失。 图形概要
• Synthesis, Antimicrobial Activity and Structure-Activity Relationship of Some 5-Arylidene-thiazolidine-2,4-dione Derivatives
  作者：Raíssa de Paiva、Jamerson da Silva、Hudieyllen Moreira、Osvaldo Pinto、Lilian Camargo、Plínio Naves、Ademir Camargo、Luciano Ribeiro、Luciana Ramos

  DOI：10.21577/0103-5053.20180167

  日期：——

  Derivatives of the thiazolidine-2,4-dione core represent a heterocyclic class with several correlated properties. In this context, the synthesis of structural analogues of these bioactive substances becomes attractive in the field of medicinal chemistry. These analogues act as antimicrobial agents against Gram-positives pathogens. The present work aimed to synthesize 10 different derivatives of 5-

  噻唑烷-2,4-二酮核的衍生物代表具有几个相关性质的杂环类。在这种情况下，这些生物活性物质的结构类似物的合成在药物化学领域变得有吸引力。这些类似物充当针对革兰氏阳性病原体的抗菌剂。本工作旨在在无溶剂反应介质中使用尿素作为催化剂，合成10种亚芳基噻唑烷-2,4-二酮的10种不同衍生物，收率范围为45％至99％。获得的化合物已针对金黄色葡萄球菌ATCC 29213进行了抗菌分析。两种化合物的最低抑菌浓度分别为62.5和32.5μgmL，最低杀菌浓度为<500μgmL，证明了它们的抗菌潜能。进行主成分分析以区分活性和非活性类别的化合物。需要四个几何和电子分子描述符来完全区分化合物。所选择的描述符可以指导我们设计具有增强活性的新的5-亚芳基-噻唑烷-2,4-二酮衍生物。
• Synthesis and in vivo antidiabetic activity of novel dispiropyrrolidines through [3+2] cycloaddition reactions with thiazolidinedione and rhodanine derivatives
  作者：Ramalingam Murugan、S. Anbazhagan、S. Sriman Narayanan

  DOI：10.1016/j.ejmech.2009.03.035

  日期：2009.8

  reaction with 5-arylidene-1,3-thiazolidine-2,4-dione and 5-arylidene-4-thioxo-1,3-thiazolidine-2-one derivatives as dipolarophiles. The structure and stereochemistry of the cycloadduct have been established by single crystal X-ray structure and spectroscopic techniques. Molecular docking studies were performed on 1FM9 protein. The synthesized compounds were screened for their antidiabetic activity on male

  通过与5-亚芳基-1,3-噻唑烷-2,4-二酮和5-亚芳基-4-硫代-1,3-噻唑烷-的1,3-偶极环加成反应完成了一系列新型双螺并吡咯烷的合成。 2-one衍生物为双极性亲和剂。环加合物的结构和立体化学已经通过单晶X射线结构和光谱技术确定。对1FM9蛋白进行了分子对接研究。筛选合成的化合物对雄性Wistar大鼠的抗糖尿病活性。