(5Z)-5-benzylidene-2-ethylsulfanyl-3,5-dihydroimidazol-4-one | 17886-50-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (5Z)-5-benzylidene-2-ethylsulfanyl-3,5-dihydroimidazol-4-one
• 英文别名: (5Z)-5-benzylidene-2-ethylsulfanyl-3,5-dihydro-4H-imidazol-4-one；2-ethylmercapto-5-benzylidene-3,5-dihydro-imidazol-4-one；2-Aethylmercapto-5-benzyliden-3,5-dihydro-imidazol-4-on；5-benzylidene-2-(ethylsulfanyl)-3,5-dihydro-4H-imidazol-4-one；(4Z)-4-benzylidene-2-ethylsulfanyl-1H-imidazol-5-one
• CAS: 17886-50-9
• 化学式: C₁₂H₁₂N₂OS
• 分子量: 232.306
• InChiKey: NOBLHNZMOKWDBT-NTMALXAHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (5Z)-5-benzylidene-2-ethylsulfanyl-3,5-dihydroimidazol-4-one 在 sodium acetate 作用下， 以 四氢呋喃 为溶剂， 生成 (5Z)-2-[4-[2-[2-(2-aminoethoxy)ethoxy]ethoxy]anilino]-4-benzylidene-3,5-dihydroimidazol-5-one
  参考文献：
  名称：

  Chemical synthesis and biological validation of immobilized protein kinase inhibitory Leucettines

  摘要：

  Leucettines, a family of marine sponge-derived 2-aminoimidazolone alkaloids, are potent inhibitors of DYRKs (dual-specificity, tyrosine phosphoiylation regulated kinases) and CLKs (cdc2-like kinases). They constitute promising pharmacological leads for the treatment of several diseases, including Alzheimer's disease and Down syndrome. In order to investigate the scope of potential targets of Leucettine L41, a representative member of the chemical class, we designed an affinity chromatography strategy based on agarose-immobilized leucettines. A synthesis protocol for the attachment of a polyethylene (3 or 4 units) linker to L41 was first established. The linker attachment site on L41 was selected on the basis of the co-crystal structure of L41 with several kinases. L41 was then covalently bound to agarose beads through the primary amine located at the end of the linker. Control, kinase inactive Leucettine was also immobilized, as well as free linker devoid of ligand. Extracts of several mouse tissues revealed a complex pattern of interacting proteins, some of which probably resulting from non-specific, hydrophobic binding, while others representing bona fide Leucettine-interacting proteins. DYRK1A and GSK-3 (glycogen synthase kinase-3) were confirmed as interacting targets by Western blotting in various mouse tissues. The Leucettine affinity chromatography resin constitutes a powerful tool to purify and identify the targets of this new promising therapeutic class of molecules. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.01.035
• 作为产物：
  描述：

  苯甲醛 在 sodium acetate 、 potassium carbonate 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 14.33h， 生成 (5Z)-5-benzylidene-2-ethylsulfanyl-3,5-dihydroimidazol-4-one
  参考文献：
  名称：

  激酶抑制剂亮西汀家族的构效关系

  摘要：

  蛋白激酶 DYRK1A 与阿尔茨海默病、唐氏综合症、糖尿病、病毒感染和白血病有关。Leucettines 是一种源自海绵生物碱 Leucettamine B 的 2-氨基咪唑啉-4-ones 家族，已被开发为 DYRKs（双特异性，酪氨酸磷酸化调节激酶）和 CLKs（cdc2 样激酶）的药理学抑制剂。我们在此报告 68 种亮氨酸的合成和构效关系 (SAR)。在 11 种纯化激酶和 5 种细胞测定中测试亮氨酸：(1) CLK1 pre-mRNA 剪接，(2) Threonine-212-Tau 磷酸化，(3) 谷氨酸诱导的细胞死亡，(4) 自噬和 (5) 拮抗作用配体激活的大麻素受体 CB1。对 DYRK1A 观察到的亮西汀 SAR 与 CLK1、CLK4、DYRK1B 和 DYRK2 基本相同。DYRK3 和 CLK3 对亮氨酸不太敏感。相比之下，细胞 SAR 突出了特定激酶靶标的抑制与一

  DOI：

  10.1021/acs.jmedchem.1c01141

文献信息

• REACTION OF 2-THIOHYDANTOINS WITH SOME DIAZOALKANES AND SOME AMINES
  作者：Ahmed A. El-barbary、Youssef L. Aly、Abdel-Fatah M. Hashem、Ashraf A. El-shehawy

  DOI：10.1080/10426500008043673

  日期：2000.5.1

  reacting 2-alkylthiohydantoins (IIla) and (XII), respectively, with morpholine and/or piperidine. Moreover, treating of two equivalents of XIVa-d with one equivalent of piperazine afforded 1,4[di-(5-phenylmethylene-hydantoinyl)]-piperazines (XVIa,b). The behaviour of 2-alkylthiohydantoins towards alanine and anthranilic acid was also investigated. The structure of the products was established by correct

  摘要 2-硫代乙内酰脲衍生物与作为重氮甲烷的重氮烷反应。研究了二苯基重氮甲烷和/或9-重氮芴。通过 2-硫代乙内酰脲 (Ia,b) 和 (X) 与重氮甲烷的反应制备了几种 2-硫代乙内酰脲 (IIa,b)、(IIIa,b)、(XI) 和 (XII)。2-吗啉-和/或2-哌啶基-糖脒(VIIa,b)和(XVa,b)分别通过使2-烷硫基乙内酰脲(IIla)和(XII)与吗啉和/或哌啶反应来制备。此外，用一当量的哌嗪处理两当量的 XIVa-d 得到 1,4[二-(5-苯基亚甲基-乙内酰脲基)]-哌嗪 (XVIa,b)。还研究了 2-烷硫基乙内酰脲对丙氨酸和邻氨基苯甲酸的行为。
• GFP-related chromophores: photoisomerization, thermal reversion, and DNA labelling
  作者：Martin S. Faillace、Ekaterina A. Dolgopolova、Noelia M. Ceballos、E. Nahir Ruiz Pereyra、Lucia Lanfri、Gustavo A. Argüello、Maximiliano Burgos Paci、Natalia B. Shustova、Walter J. Peláez

  DOI：10.1039/d3cp01655b

  日期：——

  photochemical properties of 4-hydroxybenzylidene imidazolinone (HBI), a GFP-related chromophore, imidazolidinone and imidazothiazolone analogues have been studied as fluorescent probes. Their photoisomerization and their thermal reversion were studied under 365-nm-irradiation, resulting in observation of an enthalpy–entropy compensation effect. Theoretical studies were carried out to shed light on the

  由于密闭环境对 4-羟基苯亚甲基咪唑啉酮 (HBI)（一种 GFP 相关发色团）的光化学性质有显着影响，咪唑啉酮和咪唑并噻唑酮类似物已被研究作为荧光探针。在 365 nm 照射下研究了它们的光致异构化和热回复，从而观察到了熵补偿效应。进行了理论研究以阐明热回复机制。此外，在 dsDNA 存在下，亚苄基咪唑噻唑酮的光物理研究揭示了荧光增强。所制备的化合物可被视为详细研究物理化学、生物化学或生物系统的有价值的工具。
• Johnson; Nicolet, Journal of the American Chemical Society, 1912, vol. 34, p. 1052
  作者：Johnson、Nicolet

  DOI：——

  日期：——
• Chemical synthesis and biological validation of immobilized protein kinase inhibitory Leucettines
  作者：Guillaume Burgy、Tania Tahtouh、Emilie Durieu、Béatrice Foll-Josselin、Emmanuelle Limanton、Laurent Meijer、François Carreaux、Jean-Pierre Bazureau

  DOI：10.1016/j.ejmech.2013.01.035

  日期：2013.4

  Leucettines, a family of marine sponge-derived 2-aminoimidazolone alkaloids, are potent inhibitors of DYRKs (dual-specificity, tyrosine phosphoiylation regulated kinases) and CLKs (cdc2-like kinases). They constitute promising pharmacological leads for the treatment of several diseases, including Alzheimer's disease and Down syndrome. In order to investigate the scope of potential targets of Leucettine L41, a representative member of the chemical class, we designed an affinity chromatography strategy based on agarose-immobilized leucettines. A synthesis protocol for the attachment of a polyethylene (3 or 4 units) linker to L41 was first established. The linker attachment site on L41 was selected on the basis of the co-crystal structure of L41 with several kinases. L41 was then covalently bound to agarose beads through the primary amine located at the end of the linker. Control, kinase inactive Leucettine was also immobilized, as well as free linker devoid of ligand. Extracts of several mouse tissues revealed a complex pattern of interacting proteins, some of which probably resulting from non-specific, hydrophobic binding, while others representing bona fide Leucettine-interacting proteins. DYRK1A and GSK-3 (glycogen synthase kinase-3) were confirmed as interacting targets by Western blotting in various mouse tissues. The Leucettine affinity chromatography resin constitutes a powerful tool to purify and identify the targets of this new promising therapeutic class of molecules. (C) 2013 Elsevier Masson SAS. All rights reserved.
• Structure–Activity Relationship in the Leucettine Family of Kinase Inhibitors
  作者：Tania Tahtouh、Emilie Durieu、Benoît Villiers、Céline Bruyère、Thu Lan Nguyen、Xavier Fant、Kwang H. Ahn、Leepakshi Khurana、Emmanuel Deau、Mattias F. Lindberg、Elodie Sévère、Frédéric Miege、Didier Roche、Emmanuelle Limanton、Jean-Martial L’Helgoual’ch、Guillaume Burgy、Solène Guiheneuf、Yann Herault、Debra A. Kendall、François Carreaux、Jean-Pierre Bazureau、Laurent Meijer

  DOI：10.1021/acs.jmedchem.1c01141

  日期：2022.1.27

  2-aminoimidazolin-4-ones derived from the marine sponge alkaloid Leucettamine B, have been developed as pharmacological inhibitors of DYRKs (dual specificity, tyrosine phosphorylation regulated kinases) and CLKs (cdc2-like kinases). We report here on the synthesis and structure–activity relationship (SAR) of 68 Leucettines. Leucettines were tested on 11 purified kinases and in 5 cellular assays: (1) CLK1 pre-mRNA

  蛋白激酶 DYRK1A 与阿尔茨海默病、唐氏综合症、糖尿病、病毒感染和白血病有关。Leucettines 是一种源自海绵生物碱 Leucettamine B 的 2-氨基咪唑啉-4-ones 家族，已被开发为 DYRKs（双特异性，酪氨酸磷酸化调节激酶）和 CLKs（cdc2 样激酶）的药理学抑制剂。我们在此报告 68 种亮氨酸的合成和构效关系 (SAR)。在 11 种纯化激酶和 5 种细胞测定中测试亮氨酸：(1) CLK1 pre-mRNA 剪接，(2) Threonine-212-Tau 磷酸化，(3) 谷氨酸诱导的细胞死亡，(4) 自噬和 (5) 拮抗作用配体激活的大麻素受体 CB1。对 DYRK1A 观察到的亮西汀 SAR 与 CLK1、CLK4、DYRK1B 和 DYRK2 基本相同。DYRK3 和 CLK3 对亮氨酸不太敏感。相比之下，细胞 SAR 突出了特定激酶靶标的抑制与一