2-(benzylamino)-5-benzylidenethiazol-4(5H)-one | 78374-71-7

• 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: 2-(benzylamino)-5-benzylidenethiazol-4(5H)-one
• 英文别名: 2-[(Phenylmethyl)amino]-5-(phenylmethylene)-4-thiazolone；5-benzylidene-2-benzylimino-1,3-thiazolidin-4-one
• CAS: 78374-71-7
• 化学式: C₁₇H₁₄N₂OS
• 分子量: 294.377
• InChiKey: LVKAALLVKHHHGN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  5-(苯基亚甲基)-2-硫氧代-4-噻唑啉酮 、 苄胺 生成 2-(benzylamino)-5-benzylidenethiazol-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

• γ-Aminobutyric acid hydrochloride supported on superparamagnetic γ-Fe2O3@SiO2 as a novel heterogeneous nanocatalyst for the synthesis of 2-amino-5-alkylidene-thiazol-4-one derivatives
  作者：Hadi Mohammadi、Hamid Reza Shaterian

  DOI：10.1007/s13738-018-1527-4

  日期：2019.3

  γ-Aminobutyric acid hydrochloride immobilized on superparamagnetic γ-Fe2O3@SiO2 nanoparticles as a novel heterogeneous nanocatalyst was prepared for the first times. It was characterized by several techniques such as XRD, FT-IR, VSM, FE-SEM, EDS, and TGA analysis. The heterogeneous nanocatalyst was used for a convenient, mild, and one-pot efficient three-component preparation of 2-amino-5-alkylidene-thiazol-4-one

  γ氨基丁酸盐酸盐固定在超顺磁性了γ-Fe 2 ö 3 @SiO 2个纳米颗粒作为一种新颖的多相纳米催化剂是用于第一时间制备。它的特征在于多种技术，例如XRD，FT-IR，VSM，FE-SEM，EDS和TGA分析。该多相纳米催化剂用于在室温下绿色条件下方便，温和且一锅高效地制备2-氨基-5-亚烷基-噻唑-4-酮衍生物的三组分。该方法的主要优点是易于通过外部磁体从反应混合物中回收稳定的纳米催化剂。
• Formation of ionic carbon nitride towards an environmentally friendly synthesis of 2-amino-5-alkylidene-thiazol-4-one
  作者：Najmedin Azizi、Navid Habibnejad、Tahereh Soleymani Ahooie

  DOI：10.1016/j.molliq.2022.120625

  日期：2022.12

  template-free ionic carbon nitride nanotubes (K-g-C3N4) were created via thermal polymerizing and aqueous alkaline liquid-phase exfoliation. The characterization of alkaline K-doped ionic graphitic carbon nitride (K-g-C3N4) was determined by FT-IR, SEM, EDS, and TGA analysis. A simple, facile, and efficient synthesis of 2-amino-5-alkylidene-thiazol-4-ones derivatives via a multicomponent reaction of various

  石墨氮化碳 (gC 3 N 4 ) 具有类似于石墨的层状结构，并在有机转化中提供令人兴奋和独特的支持。使用边缘功能化的石墨氮化碳通过掺杂各种官能团并将其转变为另一种形态已成为近十年来关注的焦点。具有弱碱性的富氮结构；因此，它必须通过各种功能化来改善其性能。在此，首次通过热聚合和水性碱性液相剥离制备了无模板离子氮化碳纳米管（KgC 3 N 4 ）。碱性K掺杂离子石墨碳氮化碳（KgC 3N 4 ) 通过FT-IR、SEM、EDS和TGA分析确定。 使用可重复使用的 KgC 3 N 4作为绿色催化剂，通过各种醛、胺和罗丹宁在乙醇中的多组分反应，简单、简便、高效地合成 2-氨基-5-亚烷基-噻唑-4-酮衍生物。发达。通过用罗丹明改变醛和胺的结构来探索反应范围。各种 2-氨基-5-亚烷基-噻唑-4-酮在 60-180 分钟内的产率范围在 65% 和 96% 之间。由于 KgC 3 N 4的异质性，催
• 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.