5-(4-benzyloxybenzylidene)-2-thioxothiazolidin-4-one | 168550-07-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 5-(4-benzyloxybenzylidene)-2-thioxothiazolidin-4-one
• 英文别名: 5-[(4-phenylmethoxyphenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one
• CAS: 168550-07-0
• 化学式: C₁₇H₁₃NO₂S₂
• mdl: MFCD00300331
• 分子量: 327.428
• InChiKey: LNPKMUHSBCXBNB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  95.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-(4-benzyloxybenzylidene)-2-thioxothiazolidin-4-one 、 苄胺 生成 5-[4-(benzyloxy)benzylidene]-2-(benzylamino)thiazol-4(5H)-one
  参考文献：
  名称：

  Xanthine oxidase inhibitory properties and anti-inflammatory activity of 2-amino-5-alkylidene-thiazol-4-ones

  摘要：

  Thirty 2-amino-5-alkylidene-thiazol-4-ones were assayed for inhibitory activity against commercial enzyme xanthine oxidase (XO) in vitro and XO in rat liver homogenate as well as for anti-inflammatory response on human peripheral blood mononuclear cells (PBMCs). 4-((2-Benzylamino-4-oxothiazol-5(4H)-ylidene)-methyl)benzonitrile showed the most potent inhibitory effect against commercial XO (IC50 = 17.16 mu g/mL) as well as against rat liver XO (IC50 = 24.50 mu g/mL). All compounds containing the 4-cyanobenzylidene group or (indol-3-yl)methylene group at the position 5 of thiazol-4-one moiety were moderately potent inhibitors of commercial XO. The assayed compounds were docked into the crystal structures of XO enzyme complexes with three diverse inhibitors (PDB codes: 1FIQ, 1VDV, and 1V97) using OEDocking software. Our results strongly point to a correlation between the data on inhibitory activity against commercial XO and data on antioxidant activity of studied compounds, screened using a lipid peroxidation (LP) method. 2-(Benzylamino)-5-((thiophen-2-yl)methylene)thiazol-4(5H)-one showed the highest anti-inflammatory response on PBMCs, exerted most probably through the NF-kappa B inhibition. Studied 2-amino-5-alkylidene-thiazol-4-ones obey the "Rule of five" and meet all criteria for good solubility and permeability. (C) 2015 Elsevier Ireland Ltd. All rights reserved.

  DOI：

  10.1016/j.cbi.2015.01.022
• 作为产物：
  描述：

  罗丹宁 、 4-苄氧基苯甲醛 在 三乙胺 作用下， 以 异丙醇 为溶剂， 反应 5.0h， 以74.8%的产率得到5-(4-benzyloxybenzylidene)-2-thioxothiazolidin-4-one
  参考文献：
  名称：

  5-Arylidenerhodanines as P-gp Modulators: An Interesting Effect of the Carboxyl Group on ABCB1 Function in Multidrug-Resistant Cancer Cells

  摘要：

  多重耐药（MDR）被认为是导致许多抗癌和抗病毒化疗失败的主要机制之一。已经开发了各种克服MDR现象的策略，其中最有吸引力的研究方向之一是抑制MDR转运蛋白，这些膜蛋白从活细胞中排出细胞毒性药物。在这里，我们报告了我们对一系列新合成的5-芳基亚硫氰酸酯的研究结果，以及它们抑制小鼠T淋巴瘤癌细胞中ABCB1外排泵的能力。在这个系列中，具有三苯胺基团和羧基的化合物特别引人注目。这些两亲性化合物显示出超过17倍于维拉帕米的外排泵抑制效果。还研究了目标亚硫氰酸酯对T淋巴瘤细胞的细胞毒性和抗增殖效应。通过分子对接研究预测了11号化合物的可能结合模式，讨论了与维拉帕米的结合模式相关的问题。

  DOI：

  10.3390/ijms231810812

文献信息

• Evaluation of the anti-inflammatory/chondroprotective activity of aldose reductase inhibitors in human chondrocyte cultures
  作者：Annamaria Panico、Rosanna Maccari、Venera Cardile、Sergio Avondo、Lucia Crascì、Rosaria Ottanà

  DOI：10.1039/c4md00556b

  日期：——

  2-Thioxo-4-thiazolidinone derivatives active as aldose reductase inhibitors were able to control key inflammatory/degenerative events induced by IL-1β in human chondrocytes, appearing to be promising candidates in the search for novel anti-inflammatory agents.

  2-硫代-4-噻唑啉酮衍生物作为醛固酮还原酶抑制剂，能够控制人软骨细胞中IL-1β诱导的关键炎症/退行性事件，似乎是寻找新型抗炎剂的有希望的候选者。