(5Z)-5-(benzo[1,3]dioxol-5-yl)methylene-2-ethylsulfanyl-3-methyl-3,5-dihydro-4H-imidazol-4-one | 954418-50-9

• 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-(benzo[1,3]dioxol-5-yl)methylene-2-ethylsulfanyl-3-methyl-3,5-dihydro-4H-imidazol-4-one
• 英文别名: (5Z)-5-[(1,3-benzodioxol-5-yl)methylene]-3-methyl-2-ethylthio-3,5-dihydro-4H-imidazol-4-one；(Z)-5-(1,3-benzodioxol-5-yl)methylene-3-methyl-2-ethylthio-3,5-dihydro-4H-imidazole-4-one；(5Z)-5-[(1,3-benzodioxol-5-yl)methylene]-3-methyl-2-ethylsulfanyl-3,5-dihydroimidazol-4-one；(5Z)-5-(1,3-benzodioxol-5-ylmethylidene)-2-ethylsulfanyl-3-methylimidazol-4-one
• CAS: 954418-50-9
• 化学式: C₁₄H₁₄N₂O₃S
• 分子量: 290.343
• InChiKey: NZMFVJNZGKELJC-POHAHGRESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  76.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (5Z)-5-(benzo[1,3]dioxol-5-yl)methylene-2-ethylsulfanyl-3-methyl-3,5-dihydro-4H-imidazol-4-one 、 异丙醇胺 反应 0.67h， 以64%的产率得到(5Z)-5-[(1,3-benzodioxol-5-yl)methylene]-2-[(2-hydroxypropyl)amino]-3-methyl-3,5-dihydro-4H-imidazol-4-one
  参考文献：
  名称：

  An Efficient Method for the Preparation of New Analogs of Leucettamine B under Solvent-Free Microwave Irradiation

  摘要：

  A simple and efficient microwave-assisted protocol has been developed for the synthesis of new 2-amino-3,4-dihydro-4H-imidazol-4-one derivatives of leucettamine B. This solvent-free protocol involves sulphur/nitrogen displacement of 2-ethylthio-5-arylidene-imidazolone 5 with a variety of functionalized polar primary amines 6 and this general method afforded a small library of the desired pure products 7a-n in yields ranging from 33 to 92% in moderate reaction times (30-100 minutes).

  DOI：

  10.3987/com-08-11594
• 作为产物：
  描述：

  在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 24.5h， 生成 (5Z)-5-(benzo[1,3]dioxol-5-yl)methylene-2-ethylsulfanyl-3-methyl-3,5-dihydro-4H-imidazol-4-one
  参考文献：
  名称：

  Synthesis of N,N′-bis(5-arylidene-4-oxo-3,5-dihydro-4H-imidazol-2-yl)diamines bearing various linkers and biological evaluation as potential inhibitors of kinases

  摘要：

  The synthesis in 4 steps of new N,N'-bis(5-arylidene-4-oxo-3,5-dihydro-4H-imidazol-2-yl)diamines issued from various symmetric primary diamines as linkers was reported. The key step of our strategy has been the sulphur/nitrogen displacement of (5Z)-5-arylidene-2-ethylsulfanyl-3,5-dihydro-4H-imidazol-4-ones 6 with respectively ethylenediamine 7a, piperazine 7b and N,N'-bis(3-aminopropyl)piperazine 7c using solvent-free reaction conditions under microwave irradiation with retention of configuration. These compounds were tested for their kinase inhibitory potencies toward four kinases (GSK-3 alpha/beta, DYRK1A, CLK1 and CLK3). Crown Copyright (C) 2012 Published by Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.08.044

文献信息

• IMIDAZAOLONE DERIVATIVES,PREPARATION THEREOF AND BIOLOGICAL USE OF SAME
  申请人：Carreaux Francois

  公开号：US20100216855A1

  公开（公告）日：2010-08-26

  Imidazolone derivatives, as medicaments, of formula wherein: R 1 ═H, C 1 to C 5 alkyl, aryl or a 5- or 6-membered heterocyclic group; Ar 1 =optionally substituted aryl or an aromatic heterocycle; R═R 2 —S—, R 3 —HN—, R 4 COHN or Ar 2 , with R 2 =a C 1 -C 5 alkyl, vinyl or vinyl(C 1 -C 5 )alkyl, nitrile or nitrile(C 1 -C 5 )alkyl, aryl or benzyl radical, which are optionally substituted; R 3 =the meanings given above and H; Ar 2 =substituted or unsubstituted aryl.

  咪唑酮衍生物，作为药物，具有以下结构：R1═H，C1到C5烷基，芳基或5-或6-成员杂环基；Ar1=可选择的取代芳基或芳香杂环；R═R2—S—，R3—HN—，R4COHN或Ar2，其中R2=一个C1-C5烷基，乙烯基或乙烯基(C1-C5)烷基，腈基或腈基(C1-C5)烷基，芳基或苄基基团，可以选择取代；R3=如上所述的含义和H；Ar2=取代或未取代的芳基。
• Synthesis and preliminary biological evaluation of new derivatives of the marine alkaloid leucettamine B as kinase inhibitors
  作者：Mansour Debdab、Stéven Renault、Olivier Lozach、Laurent Meijer、Ludovic Paquin、François Carreaux、Jean-Pierre Bazureau

  DOI：10.1016/j.ejmech.2009.10.009

  日期：2010.2

  New derivatives of the marine alkaloid leucettamine B were prepared in five steps with overall yields ranging from 23 to 30%. The key step of our strategy has been the sulfur/nitrogen displacement under solvent-free microwave irradiation of (5Z) 5-benzo[1,3]-dioxo-5-ylmethylene-2-ethylsulfanyl-3,5-dihydroimidazol-4-one 3 with a mono-protected ethylenediamine 2. After deprotection of the N-Boc group, the amino derivative of leucettamine B 5 was subjected to reductive amination in two steps with retention of configuration of the double bond, to lead to eight new analogs of leucettamine B. The effect of these compounds on CK1 alpha/beta, CDK5/p25, and GSK-3 alpha/beta were investigated. (C) 2009 Elsevier Masson SAS. All rights reserved.
• DERIVES D'IMIDAZOLONES, PROCEDE DE PREPARATION ET APPLICATIONS BIOLOGIQUES
  申请人：Universite Rennes 1

  公开号：EP2185547B1

  公开（公告）日：2017-07-19
• US8563588B2
  申请人：——

  公开号：US8563588B2

  公开（公告）日：2013-10-22
• An Efficient Method for the Preparation of New Analogs of Leucettamine B under Solvent-Free Microwave Irradiation
  作者：François Carreaux、Jean Pierre Bazureau、Mansour Debdab、Steven Renault、Samar Eid、Olivier Lozach、Laurent Meijer

  DOI：10.3987/com-08-11594

  日期：——

  A simple and efficient microwave-assisted protocol has been developed for the synthesis of new 2-amino-3,4-dihydro-4H-imidazol-4-one derivatives of leucettamine B. This solvent-free protocol involves sulphur/nitrogen displacement of 2-ethylthio-5-arylidene-imidazolone 5 with a variety of functionalized polar primary amines 6 and this general method afforded a small library of the desired pure products 7a-n in yields ranging from 33 to 92% in moderate reaction times (30-100 minutes).