5-[(benzo[d][1,3]dioxol-6-yl)methylene]-2-(4-methylpiperidin-1-yl)thiazol-4(5H)-one | 296773-06-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: 5-[(benzo[d][1,3]dioxol-6-yl)methylene]-2-(4-methylpiperidin-1-yl)thiazol-4(5H)-one
• 英文别名: 5-(1,3-Benzodioxol-5-ylmethylidene)-2-(4-methylpiperidin-1-yl)-1,3-thiazol-4-one
• CAS: 296773-06-3
• 化学式: C₁₇H₁₈N₂O₃S
• 分子量: 330.408
• InChiKey: WNQFZDISXWGGGH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  76.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-甲基哌啶 、 5-(1,3-benzodioxol-5-ylmethylidene)-2-thioxo-1,3-thiazolidin-4-one 生成 5-[(benzo[d][1,3]dioxol-6-yl)methylene]-2-(4-methylpiperidin-1-yl)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

文献信息

• Three-component one-pot synthetic route to 2-amino-5-alkylidene-thiazol-4-ones
  作者：Marko Anderluh、Marko Jukič、Rok Petrič

  DOI：10.1016/j.tet.2008.10.045

  日期：2009.1

  A fast and straightforward three-component reaction to 2-amino-5-alkylidene-thiazol-4-ones is described. The one-pot methodology, reported for the first time, involves Knoevenagel condensation of aromatic aldehydes and rhodanine followed by displacement of the thiocarbonyl sulfur with primary or secondary amines in the same reaction mixture. The reactions were performed using a dedicated microwave reactor, which enabled short reaction times and easy work-up. (C) 2008 Elsevier Ltd. All rights reserved.
• Xanthine oxidase inhibitory properties and anti-inflammatory activity of 2-amino-5-alkylidene-thiazol-4-ones
  作者：Zaklina Smelcerovic、Andrej Veljkovic、Gordana Kocic、Denitsa Yancheva、Zivomir Petronijevic、Marko Anderluh、Andrija Smelcerovic

  DOI：10.1016/j.cbi.2015.01.022

  日期：2015.3

  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.