(5Z)-5[(1,3-benzodioxol-5-yl)methylene]-3-methyl-2-[(2-tert-butylamino)ethylcarbamate]-3,5-dihydro-4H-imidazol-4-one | 1213706-21-8

• 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[(1,3-benzodioxol-5-yl)methylene]-3-methyl-2-[(2-tert-butylamino)ethylcarbamate]-3,5-dihydro-4H-imidazol-4-one
• 英文别名: tert-butyl N-[2-[[(4Z)-4-(1,3-benzodioxol-5-ylmethylidene)-1-methyl-5-oxoimidazolidin-2-ylidene]amino]ethyl]carbamate
• CAS: 1213706-21-8
• 化学式: C₁₉H₂₄N₄O₅
• 分子量: 388.423
• InChiKey: KGERHCZCYJOTGU-LCYFTJDESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  102
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (5Z)-5[(1,3-benzodioxol-5-yl)methylene]-3-methyl-2-[(2-tert-butylamino)ethylcarbamate]-3,5-dihydro-4H-imidazol-4-one 在 甲醇 、 乙酰氯 作用下， 以 乙腈 为溶剂， 以98%的产率得到(5Z)-5-[(1,3-benzodioxol-5-yl)methylene]-3-methyl-2-[(2-aminoethyl)amino]-3,5-dihydro-4H-imidazol-4-one hydrochloride
  参考文献：
  名称：

  Synthesis and preliminary biological evaluation of new derivatives of the marine alkaloid leucettamine B as kinase inhibitors

  摘要：

  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.

  DOI：

  10.1016/j.ejmech.2009.10.009
• 作为产物：
  描述：

  N-叔丁氧羰基-1,2-乙二胺 、 (5Z)-5-(benzo[1,3]dioxol-5-yl)methylene-2-ethylsulfanyl-3-methyl-3,5-dihydro-4H-imidazol-4-one 反应 2.0h， 以69%的产率得到(5Z)-5[(1,3-benzodioxol-5-yl)methylene]-3-methyl-2-[(2-tert-butylamino)ethylcarbamate]-3,5-dihydro-4H-imidazol-4-one
  参考文献：
  名称：

  Synthesis and preliminary biological evaluation of new derivatives of the marine alkaloid leucettamine B as kinase inhibitors

  摘要：

  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.

  DOI：

  10.1016/j.ejmech.2009.10.009

文献信息

• 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.