4,4'-bis[1,3-di(tert-butoxycarbonyl)-2-imidazolidinylimino]diphenylamine | 292634-05-0

• 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: 4,4'-bis[1,3-di(tert-butoxycarbonyl)-2-imidazolidinylimino]diphenylamine
• 英文别名: Ditert-butyl 2-[4-[4-[[1,3-bis[(2-methylpropan-2-yl)oxycarbonyl]imidazolidin-2-ylidene]amino]anilino]phenyl]iminoimidazolidine-1,3-dicarboxylate
• CAS: 292634-05-0
• 化学式: C₃₈H₅₃N₇O₈
• 分子量: 735.881
• InChiKey: AVVQXOHHXDDFSF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  53
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  155
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  4,4'-bis[1,3-di(tert-butoxycarbonyl)-2-imidazolidinylimino]diphenylamine 在 三氟乙酸 作用下， 反应 0.5h， 以87%的产率得到
  参考文献：
  名称：

  New aromatic iminoimidazolidine derivatives as α 1 -adrenoceptor antagonists: a novel synthetic approach and pharmacological activity

  摘要：

  The design, synthesis and alpha(1)-adrenoceptor antagonism of a series of bis-imidazoline (1a, 2a, 3a and 4a) and bis-guanidine (1b, 2b, 3b and 4b) diphenyl derivatives are reported. All of these compounds fulfil the conditions of the most recent pharmacophore proposed for alpha(1)-adrenoceptors and found in the literature. Besides, a novel synthetic approach to the preparation of 2-(aryl-imino)imidazolidine derivatives is described. All the tested compounds, except the bis-guanidinium derivative 3b, inhibit the contractile responses induced by noradrenaline in aortic rings of rat and rabbit in a dose-dependent manner. Our results indicate that, even though some discrepancies are observed in terms of the alpha(1) subtype targeted by this new family of compounds, they show an interesting profile as antagonists of alpha(1)-adrenoceptors and a new prototype, compound 1a, has been found deserving further development. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00089-4
• 作为产物：
  描述：

  4,4’-二氨基二苯胺 、 2-thioxo-imidazolidine-1,3-dicarboxylic acid di-tert-butyl ester 在 三乙胺 、 mercury dichloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以76%的产率得到4,4'-bis[1,3-di(tert-butoxycarbonyl)-2-imidazolidinylimino]diphenylamine
  参考文献：
  名称：

  New aromatic iminoimidazolidine derivatives as α 1 -adrenoceptor antagonists: a novel synthetic approach and pharmacological activity

  摘要：

  The design, synthesis and alpha(1)-adrenoceptor antagonism of a series of bis-imidazoline (1a, 2a, 3a and 4a) and bis-guanidine (1b, 2b, 3b and 4b) diphenyl derivatives are reported. All of these compounds fulfil the conditions of the most recent pharmacophore proposed for alpha(1)-adrenoceptors and found in the literature. Besides, a novel synthetic approach to the preparation of 2-(aryl-imino)imidazolidine derivatives is described. All the tested compounds, except the bis-guanidinium derivative 3b, inhibit the contractile responses induced by noradrenaline in aortic rings of rat and rabbit in a dose-dependent manner. Our results indicate that, even though some discrepancies are observed in terms of the alpha(1) subtype targeted by this new family of compounds, they show an interesting profile as antagonists of alpha(1)-adrenoceptors and a new prototype, compound 1a, has been found deserving further development. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00089-4

文献信息

• New aromatic iminoimidazolidine derivatives as α 1 -adrenoceptor antagonists: a novel synthetic approach and pharmacological activity
  作者：Christophe Dardonville、Pilar Goya、Isabel Rozas、Angela Alsasua、Mª Isabel Martı́n、Mª José Borrego

  DOI：10.1016/s0968-0896(00)00089-4

  日期：2000.7

  The design, synthesis and alpha(1)-adrenoceptor antagonism of a series of bis-imidazoline (1a, 2a, 3a and 4a) and bis-guanidine (1b, 2b, 3b and 4b) diphenyl derivatives are reported. All of these compounds fulfil the conditions of the most recent pharmacophore proposed for alpha(1)-adrenoceptors and found in the literature. Besides, a novel synthetic approach to the preparation of 2-(aryl-imino)imidazolidine derivatives is described. All the tested compounds, except the bis-guanidinium derivative 3b, inhibit the contractile responses induced by noradrenaline in aortic rings of rat and rabbit in a dose-dependent manner. Our results indicate that, even though some discrepancies are observed in terms of the alpha(1) subtype targeted by this new family of compounds, they show an interesting profile as antagonists of alpha(1)-adrenoceptors and a new prototype, compound 1a, has been found deserving further development. (C) 2000 Elsevier Science Ltd. All rights reserved.