3-(4-methylphenyl)thiazolidine-2,4-dione | 16240-04-3

• 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: 3-(4-methylphenyl)thiazolidine-2,4-dione
• 英文别名: 3-p-tolylthiazolidine-2,4-dione；3-p-tolyl-thiazolidine-2,4-dione；3-p-Tolyl-thiazolidin-2,4-dion；3-(4-Tolyl)-2.4-thiazolidindion；3-p-Tolyl-thiazolidin-2,4-dion；3-p-Tolyl-2,4-thiazolidindion；3-(4-Methylphenyl)-1,3-thiazolidine-2,4-dione
• CAS: 16240-04-3
• 化学式: C₁₀H₉NO₂S
• mdl: MFCD00175796
• 分子量: 207.253
• InChiKey: ICKHEFLHFUVLBO-UHFFFAOYSA-N

物化性质

• 熔点：
  162 °C(Solv: water (7732-18-5))
• 沸点：
  348.2±35.0 °C(Predicted)
• 密度：
  1.357±0.06 g/cm3(Predicted)

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：
  0.2
• 拓扑面积：
  62.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(4-methylphenyl)thiazolidine-2,4-dione 以 乙醚 、 氯仿 为溶剂， 生成 5-[1-(2-methoxy-phenyl)-ethylidene]-3-p-tolyl-thiazolidine-2,4-dione
  参考文献：
  名称：

  On the Reactivity of the Exocyclic Double Bond in 5-Arylidene-3-aryl-2,4-thiazolidinediones; Their Reaction with Diazoalkanes, p-Thiocresol and Piperidine

  摘要：

  DOI：

  10.1021/ja01495a051
• 作为产物：
  描述：

  3-(4-甲基苯基)-2-硫酮-1,3-噻唑啉-4-酮 在 sodium tungstate 、 双氧水 作用下， 以 乙酸乙酯 为溶剂， 反应 15.0h， 以14%的产率得到3-(4-methylphenyl)thiazolidine-2,4-dione
  参考文献：
  名称：

  Thiazolidinone–Peptide Hybrids as Dengue Virus Protease Inhibitors with Antiviral Activity in Cell Culture

  摘要：

  The protease of dengue virus is a promising target for antiviral drug discovery. We here report a new generation of peptide hybrid inhibitors of dengue protease that incorporate N-substituted 5-arylidenethiazolidinone heterocycles (rhodanines and thiazolidinediones) as N-terminal capping groups of the peptide moiety. The compounds were extensively characterized with respect to inhibition of various proteases, inhibition mechanisms, membrane permeability, antiviral activity, and cytotoxicity in cell culture. A sulfur/oxygen exchange in position 2 of the capping heterocycle (thiazolidinedione-capped vs rhodanine-capped peptide hybrids) has a significant effect on these properties and activities. The most promising in vitro affinities were observed for thiazolidinedione-based peptide hybrids containing hydrophobic groups with K-i values between 1.5 and 1.8 mu M and competitive inhibition mechanisms. Rhodanine-capped peptide hybrids with hydrophobic substituents have, in correlation with their membrane permeability, a more pronounced antiviral activity in cell culture than the thiazolidinediones.

  DOI：

  10.1021/jm400828u

文献信息

• Synthesis of heterocycles via enamines—X
  作者：Harjit Singh、Paramjit Singh、Kanwal Deep

  DOI：10.1016/s0040-4020(01)88577-x

  日期：1983.1

  2,4-Dioxathiazolidine derivatives (7) have been obtained in synthetically useful yields by the condensations of easily available 1-substituted-4,4,6-trimethyl-1,4-dihydropyrimidine-2(3H) thione derivatives (4) and α-halogenated carboxylic acids in aqueous medium. The condensations of 4 with α-haloketones in ethanol containing cone HCl furnish 2-oxa-4-thiazolines (8). The condensations of N,N-dialkyl-N'-aryl

  2,4- Dioxathiazolidine衍生物（7）已在合成有用的产率通过的缩合获得容易获得的1-取代-4,4,6-三甲基-1,4-二氢嘧啶-2（3H）硫酮衍生物（4）和在水性介质中的α-卤代羧酸。在含有浓HCl的乙醇中，4与α-卤代酮的缩合反应提供了2-oxa-4-thiazolines（8）。在浓HCl存在下，N，N-二烷基-N'-芳基硫脲或芳基硫代氨基甲酸酯与α-氯代羧酸和α-卤代酮的缩合分别得到7和8。
• Novel <i>N</i>-Phenyl–Substituted Thiazolidinediones Protect Neural Cells against Glutamate- and tBid-Induced Toxicity
  作者：Sina Oppermann、Florian C. Schrader、Katharina Elsässer、Amalia M. Dolga、Anna Lena Kraus、Nunzianna Doti、Christof Wegscheid-Gerlach、Martin Schlitzer、Carsten Culmsee

  DOI：10.1124/jpet.114.213777

  日期：2014.8

  Mitochondrial demise is a key feature of progressive neuronal death contributing to acute and chronic neurological disorders. Recent studies identified a pivotal role for the BH3-only protein B-cell lymphoma-2 interacting domain death antagonist (Bid) for such mitochondrial damage and delayed neuronal death after oxygen-glucose deprivation, glutamate-induced excitotoxicity, or oxidative stress in vitro and after cerebral ischemia in vivo. Therefore, we developed new N -phenyl–substituted thiazolidine-2,4-dione derivatives as potent inhibitors of Bid-dependent neurotoxicity. The new compounds 6, 7, and 16 were identified as highly protective by extensive screening in a model of glutamate toxicity in immortalized mouse hippocampal neurons (HT-22 cells). These compounds significantly prevent truncated Bid–induced toxicity in the neuronal cell line, providing strong evidence that inhibition of Bid was the underlying mechanism of the observed protective effects. Furthermore, Bid-dependent hallmarks of mitochondrial dysfunction, such as loss of mitochondrial membrane potential, ATP depletion, as well as impairments in mitochondrial respiration, are significantly prevented by compounds 6, 7, and 16. Therefore, the present study identifies a class of N -phenyl thiazolidinediones as novel Bid-inhibiting neuroprotective agents that provide promising therapeutic perspectives for neurodegenerative diseases, in which Bid-mediated mitochondrial damage and associated intrinsic death pathways contribute to the underlying progressive loss of neurons.

  线粒体死亡是导致急性和慢性神经系统疾病的渐进性神经元死亡的一个关键特征。最近的研究发现，纯 BH3 蛋白 B 细胞淋巴瘤-2 交互结构域死亡拮抗剂（Bid）在体外氧-葡萄糖剥夺、谷氨酸诱导的兴奋毒性或氧化应激以及体内脑缺血后的线粒体损伤和延缓神经元死亡中起着关键作用。因此，我们开发了新的 N-苯基取代噻唑烷-2,4-二酮衍生物，作为 Bid 依赖性神经毒性的强效抑制剂。在永生化小鼠海马神经元（HT-22 细胞）谷氨酸毒性模型中，通过广泛筛选，确定了新化合物 6、7 和 16 具有高度保护作用。这些化合物能明显防止截短 Bid 诱导的神经元细胞系毒性，有力地证明了抑制 Bid 是观察到的保护作用的基本机制。此外，Bid 依赖性线粒体功能障碍的特征，如线粒体膜电位丧失、ATP 耗竭以及线粒体呼吸障碍，都能被化合物 6、7 和 16 明显阻止。因此，本研究发现了一类 N-苯基噻唑烷二酮类化合物，它们是新型的 Bid 抑制神经保护剂，为神经退行性疾病的治疗提供了广阔的前景，在神经退行性疾病中，Bid 介导的线粒体损伤和相关的内在死亡途径是神经元逐渐丧失的根本原因。
• THE REACTIONS OF THE FORMAMIDINES. VIII. SOME THIAZOLIDONE DERIVATIVES.
  作者：F. B. Dains、Roy Irvin、C. G. Harrel

  DOI：10.1021/ja01436a027

  日期：1921.3
• Fischer,E. et al., Zeitschrift fur Chemie, 1975, vol. 15, p. 480 - 481
  作者：Fischer,E. et al.

  DOI：——

  日期：——
• Singh,P.R., Indian Journal of Chemistry, 1963, vol. 1, p. 100 - 101
  作者：Singh,P.R.

  DOI：——

  日期：——