(5Z)-5-[(E)-3-phenylallylidene]thiazolidine-2,4-dione | 1307299-57-5

• 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: (5Z)-5-[(E)-3-phenylallylidene]thiazolidine-2,4-dione
• 英文别名: (Z)-5-((E)-3-phenylallylidene)thiazolidine-2,4-dione；(Z)-5-[(E)-3-phenylallylidene]thiazolidine-2,4-dione；5-cinnamylidene-thiazolidine-2,4-dione；5-Cinnamyliden-thiazolidin-2,4-dion；(5Z)-5-[(2E)-3-phenylprop-2-en-1-ylidene]-1,3-thiazolidine-2,4-dione；(5Z)-5-[(E)-3-phenylprop-2-enylidene]-1,3-thiazolidine-2,4-dione
• CAS: 1307299-57-5
• 化学式: C₁₂H₉NO₂S
• 分子量: 231.275
• InChiKey: XABHYXPBBJGVRA-DODKFZKMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  (5Z)-5-[(E)-3-phenylallylidene]thiazolidine-2,4-dione 、 1-溴-3-氯丙烷 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 以84%的产率得到(5Z)-3-(3-chloropropyl)-5-[(E)-3-phenylallylidene]thiazolidine-2,4-dione
  参考文献：
  名称：

  Discovery of novel cinnamylidene-thiazolidinedione derivatives as PTP-1B inhibitors for the management of type 2 diabetes

  摘要：

  对肥胖症相关蛋白酪氨酸磷酸酶1B（PTP-1B）的抑制剂，进行了肉桂醛基噻唑烷二酮衍生物的合成、生物评价、in silico结合亲和力预测和三维定量构效关系（3D-QSAR）研究。

  DOI：

  10.1039/c6ra24501c
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 盐酸 作用下， 生成 (5Z)-5-[(E)-3-phenylallylidene]thiazolidine-2,4-dione
  参考文献：
  名称：

  Zipser, Monatshefte fur Chemie, 1902, vol. 23, p. 964

  摘要：

  DOI：

文献信息

• Diverse 3-Methylthio-4-Substituted Maleimides through a Novel Rearrangement Reaction: Synthesis and Selective Cell Imaging
  作者：Luan V. Meirelles、Pedro P. de Castro、Saulo T. A. Passos、Bernardo B. P. P. Carvalho、Chris H. J. Franco、José R. Correa、Brenno A. D. Neto、Giovanni W. Amarante

  DOI：10.1021/acs.joc.1c02714

  日期：2022.3.4

  metal-free protocol for the preparation of fluorescent and non-fluoresent 3-methylthio-4-arylmaleimides in a single step through a new rearrangement from thiazolidine-2,4-diones is described. By employing the optimized reaction conditions, a broad scope of derivatives was prepared in ≤97% yield. The reaction tolerated several substituted aryl groups, including the challenging preparation of pyridyl-containing

  描述了通过从 thiazolidine-2,4-diones 进行新的重排，一步制备荧光和非荧光 3-methylthio-4-arylmaleimides 的无过渡金属协议。通过采用优化的反应条件，以≤97%的收率制备了广泛的衍生物。该反应耐受几个取代的芳基，包括具有挑战性的含吡啶基衍生物的制备。一系列对照实验强烈表明新的重排涉及关键的异氰酸酯中间体和与原位生成的甲基硫代甲基乙酸酯的进一步反应。还研究了一些合成衍生物的光物理性质及其在活细胞成像中的用途，
• Design, Synthesis and Characterization of Some Novel 3-Coumarinyl- 5-aryliden-1,3-thiazolidine-2,4-diones and Their Antioxidant Activity
  作者：Milan Čačić、Maja Molnar

  DOI：10.1515/znb-2011-0210

  日期：2011.2.1

  In our effort to obtain biologically active compounds, new 3,5-disubstituted 1,3-thiazolidine-2,4- diones (5a - r) were synthesized. A series of 5-arylmethylidene-1,3-thiazolidine-2,4-diones (3a - r) were prepared by Knoevenagel reaction from 1,3-thiazolidine-2,4-dione (2) and appropriate aromatic aldehydes. Condensation of 3a - r with 7-hydroxy-4-bromomethyl-2-oxo-2H-chromene (1) afforded novel 3-(7-hydroxy-2-oxo-2H-chromen-4-ylmethyl)-5-arylidene-1,3-thiazolidine-2,4-diones 5a - r. Compounds 3a - r and 5a - r were evaluated for their antioxidant activity (DPPH free radical scavenging activity).

  在我们努力获取生物活性化合物的过程中，合成了新的3,5-二取代-1,3-噻唑烷-2,4-二酮(5a - r)。通过Knoevenagel反应从1,3-噻唑烷-2,4-二酮(2)和适当的芳香醛制备了一系列5-芳基甲基亚烯-1,3-噻唑烷-2,4-二酮(3a - r)。将3a - r与7-羟基-4-溴甲基-2-氧代-2H-咖啡因(1)进行缩合反应，得到了新颖的3-(7-羟基-2-氧代-2H-咖啡因-4-基甲基)-5-芳基亚烯-1,3-噻唑烷-2,4-二酮5a - r。化合物3a - r和5a - r被评估其抗氧化活性(DPPH自由基清除活性)。
• Pharmaceutical Preparations Comprising Insulin, Zinc Ions and Zinc-Binding Ligand
  申请人：Kaarsholm Niels Christian

  公开号：US20090123563A1

  公开（公告）日：2009-05-14

  Novel preparations comprising branched ligands for the HisB10 Zn2+ sites of the R-state insulin hexamer. The preparations have a prolonged action designed for flexible injection regimes.

  这段话的中文翻译如下：使用分支配体的新型制备物，用于R-状态胰岛素六聚体的HisB10 Zn2+位点。这些制备物具有长效作用，旨在为灵活的注射方案设计。
• Tau-Centric Multitarget Approach for Alzheimer’s Disease: Development of First-in-Class Dual Glycogen Synthase Kinase 3β and Tau-Aggregation Inhibitors
  作者：Annachiara Gandini、Manuela Bartolini、Daniele Tedesco、Loreto Martinez-Gonzalez、Carlos Roca、Nuria E. Campillo、Josefa Zaldivar-Diez、Concepción Perez、Giampaolo Zuccheri、Andrea Miti、Alessandra Feoli、Sabrina Castellano、Sabrina Petralla、Barbara Monti、Martina Rossi、Fabio Moda、Giuseppe Legname、Ana Martinez、Maria Laura Bolognesi

  DOI：10.1021/acs.jmedchem.8b00610

  日期：2018.9.13

  Several findings propose the altered tau protein network as an important target for Alzheimer's disease (AD). Particularly, two points of pharmacological intervention can be envisaged: inhibition of phosphorylating tau kinase GSK-3 beta and tau aggregation process. On the basis of this consideration and on our interest in multitarget paradigms in AD, we report on the discovery of 2,4-thiazolidinedione derivatives endowed with such a profile. 28 and 30 displayed micromolar IC50 values toward GSK-3 beta, together with the capacity of inhibiting AcPHF6 aggregation of 60% and 80% at 10 ktM, respectively. In addition, they showed PAMPA-BBB permeability, together with a suitable cellular safety profile. 30 also displayed inhibition of both K18 and full-length tau aggregations. Finally, both compounds were able to improve cell viability in an okadaic acid-induced neurodegeneration cell model. To the best of our knowledge, 28 and 30 are the first balanced, nontoxic, dual-acting compounds hitting tau cascade at two different hubs.
• Study of biophysical properties, synthesis and biological evaluations of newer thiazolidine-2,4-dione conjugates
  作者：Patel, Jaydeep A.、Patel, Navin B.、Patel, Parth P.

  DOI：10.56042/ijc.v61i10.67207

  日期：——