3-phenylethylthiazolidine-2,4-dione | 86106-18-5

• 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-phenylethylthiazolidine-2,4-dione
• 英文别名: 3-phenethylthiazolidine-2,4-dione；3-(2-Phenylethyl)-1,3-thiazolidine-2,4-dione
• CAS: 86106-18-5
• 化学式: C₁₁H₁₁NO₂S
• mdl: MFCD03566879
• 分子量: 221.28
• InChiKey: VQBZVXONHFRPQE-UHFFFAOYSA-N

物化性质

• 熔点：
  111-113 °C(Solv: dichloromethane (75-09-2); hexane (110-54-3))
• 沸点：
  362.3±35.0 °C(Predicted)
• 密度：
  1.297±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.272
• 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-phenylethylthiazolidine-2,4-dione 在 盐酸 、 sodium tetrahydroborate 、 对甲苯磺酸 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 100.0h， 生成 N-(2-phenylethyl)-4,5-thiazolin-2-one
  参考文献：
  名称：

  噻酰亚胺-烯烃环化

  摘要：

  在氮原子上被不同的π-亲核试剂取代的噻唑烷二酮3-8的区域选择性NaBH 4 / H +还原以良好的产率提供羟基内酰胺9-14。后面的化合物是α-酰化铵离子16的极好的前体，可以在HCOOH中进行立体选择环化，以产生具有不同结构的新型杂环系统。由于闭环中的立体电子控制，很容易实现立体选择性合成，例如8a到24的转换。

  DOI：

  10.1016/0040-4020(82)80103-8
• 作为产物：
  描述：

  2,4-噻唑烷二酮 、 乙基溴苯 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 3-phenylethylthiazolidine-2,4-dione
  参考文献：
  名称：

  作为潜在胰腺脂肪酶抑制剂的新型吲哚噻唑烷二酮混合类似物的合成、分子建模和药理学评价

  摘要：

  合成、表征并评估了一系列新型吲哚-噻唑烷二酮杂合类似物（7a 至 7 u）的潜在胰脂肪酶 (PL) 抑制作用。在筛选的分析...

  DOI：

  10.1080/07391102.2023.2293255

文献信息

• Design, synthesis, and biological activity of a novel series of 2,5-disubstituted furans/pyrroles as HIV-1 fusion inhibitors targeting gp41
  作者：Shibo Jiang、Srinivasa R. Tala、Hong Lu、Peng Zou、Ilker Avan、Tarek S. Ibrahim、Nader E. Abo-Dya、Abdelmotaal Abdelmajeid、Asim K. Debnath、Alan R. Katritzky

  DOI：10.1016/j.bmcl.2011.08.081

  日期：2011.11

  Based on molecular docking analysis of earlier results, we designed a series of 2,5-disubstituted furans/pyrroles (5a–h) as HIV-1 entry inhibitors. Compounds were synthesized by Suzuki–Miyaura cross coupling, followed by a Knoevenagel condensation or Wittig reaction. Four of these compounds were found to be effective in inhibiting HIV-1 infection, with the best compounds being 5f and 5h, which exhibited

  基于早期结果的分子对接分析，我们设计了一系列2，5-二取代的呋喃/吡咯（5a – h）作为HIV-1进入抑制剂。化合物是通过Suzuki-Miyaura交叉偶联，然后进行Knoevenagel缩合或Wittig反应合成的。发现其中的四种化合物可有效抑制HIV-1感染，最好的化合物为5f和5h，它们对HIV-1 IIIB表现出显着的抑制作用以微摩尔水平感染，细胞毒性低。这些化合物还可以有效阻断HIV-1介导的细胞-细胞融合和gp41六螺旋束的形成，表明它们还是靶向gp41的HIV-1融合抑制剂，并有可能被开发为新型的抗HIV药物。 -1级代理商。
• Thiazolidinone–Peptide Hybrids as Dengue Virus Protease Inhibitors with Antiviral Activity in Cell Culture
  作者：Christoph Nitsche、Verena N. Schreier、Mira A. M. Behnam、Anil Kumar、Ralf Bartenschlager、Christian D. Klein

  DOI：10.1021/jm400828u

  日期：2013.11.14

  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.
• Designing of potential inhibitors against Staphylococcus aureus sortase A: Combined analogue and structure based approach with in vitro validation
  作者：K. Kranthi Raj、Veeramachaneni Ganesh Kumar、Chalasani Leela Madhuri、Pardhasaradhi Mathi、Ravulapati Durga Lakshmi、M. Ravi、B. Sri Ramudu、S.V. Venkata Rao、D. Ramachandran

  DOI：10.1016/j.jmgm.2015.05.009

  日期：2015.7

  Staphylococcus aureus sortase A is an attractive target of Gram-positive bacteria that plays a crucial role in anchoring of surface proteins to peptidoglycan present in bacterial cell wall. Inhibiting sortase A is an elementary and essential effort in preventing the pathogenesis. In this context, in silico virtual screening of in-house database was performed using ligand based pharmacophore model as a filter. The developed pharmacophore model AAHR 11 consists of two acceptors, one hydrophobic and one ring aromatic feature. Top ranked molecule KKR1 was docked into the active site of the target. After profound analysis, it was analyzed and optimized based on the observations from its binding pose orientation. Upgraded version of KKR1 was KKR2 and has improved docking score, binding interactions and best fit in the binding pocket. KKR1 along with KKR2 were further validated using 100 ns molecular dynamic studies. Both KKR1 and KKR2 contain Indole-thiazolidine moiety and were synthesized. The disk diffusion assay has good initial results (ZI of KKR1, KKR2 were 24, 38 mm at 10 mu g/mL and ZI of Ampicillin was 22 at 10 mu g/mL) and calculated MICs of the molecules (KKR1 5.56 +/- 0.28 mu g/mL, KKR2 1.32 +/- 0.12 mu g/mL, Ampicillin 8 +/- 1.1 mu g/mL) were in good agreement with standard drug Ampicillin. KKR1 has shown IC50 of 1.23 +/- 0.14 mu M whereas the optimized lead molecule KKR2 show IC50 of 0.008 +/- 0.07 mu M. Results from in silica were validated by in vitro studies and proved that indole-thiazolidine molecules would be useful for future development as lead molecules against S. aureus sortase A. (C) 2015 Elsevier Inc. All rights reserved.
• HAMERSMA, J. A. M.;SPECKAMP, W. N., TETRAHEDRON, 1982, 38, N 22, 3255-3266
  作者：HAMERSMA, J. A. M.、SPECKAMP, W. N.

  DOI：——

  日期：——
• Thia-acyliminium - olefin cyclizations
  作者：J.A.M. Hamersma、W.N. Speckamp

  DOI：10.1016/0040-4020(82)80103-8

  日期：1982.1

  the nitrogen atom with different π-nucleophiles affords hydroxylactams 9-14 in good yields. The latter compounds are excellent precursors for the α-acyliminium ion 16 and can be stereoselectively cyclized in HCOOH to yield novel heterocyclic ring systems of varied structures. Because of the stereoelectronic control in the ring closure stereoselective syntheses, such as the conversion of 8a to 24, are

  在氮原子上被不同的π-亲核试剂取代的噻唑烷二酮3-8的区域选择性NaBH 4 / H +还原以良好的产率提供羟基内酰胺9-14。后面的化合物是α-酰化铵离子16的极好的前体，可以在HCOOH中进行立体选择环化，以产生具有不同结构的新型杂环系统。由于闭环中的立体电子控制，很容易实现立体选择性合成，例如8a到24的转换。