2-{4-[3-(4-tert-butoxycarbonylaminophenyl)ureido]phenylimino}imidazolidine-1,3-dicarboxylic acid di-tert-butyl ester | 1196966-45-6

• 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-{4-[3-(4-tert-butoxycarbonylaminophenyl)ureido]phenylimino}imidazolidine-1,3-dicarboxylic acid di-tert-butyl ester
• 英文别名: Ditert-butyl 2-[4-[[4-[(2-methylpropan-2-yl)oxycarbonylamino]phenyl]carbamoylamino]phenyl]iminoimidazolidine-1,3-dicarboxylate
• CAS: 1196966-45-6
• 化学式: C₃₁H₄₂N₆O₇
• 分子量: 610.71
• InChiKey: ISZXNYUYTVPKSO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  44
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  151
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2-{4-[3-(4-tert-butoxycarbonylaminophenyl)ureido]phenylimino}imidazolidine-1,3-dicarboxylic acid di-tert-butyl ester 、 三氟乙酸 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 1-(4-aminophenyl)-3-[4-(imidazolidin-2-ylideneamino)phenyl]urea bis(trifluoroacetate)
  参考文献：
  名称：

  Asymmetrical Diaromatic Guanidinium/2-Aminoimidazolinium Derivatives: Synthesis and DNA Affinity

  摘要：

  In this paper we report the synthesis of three families of new amidine-based aromatic derivatives as potential DNA minor groove binding agents for the treatment of cancer. The preparation of monoguanidine, mono-2-aminoimidazoline, and asymmetric diphenylguanidine/2-aminoimidazoline derivatives (compounds 1a-c to 8a-c) is presented. The affinity of these substrates and of a family of mono- and bis-isoureas (previously prepared in Rozas' laboratory) for DNA was evaluated by means of DNA thermal denaturation measurements. In particular, compounds 2c, 5c, 6c, 7c, and 8c were found to bind strongly both to natural DNA and to adenine-thymine oligonucleotides, showing a preference for the adenine-thymine base pair sequences.

  DOI：

  10.1021/jm901017t
• 作为产物：
  描述：

  {4-[3-(4-aminophenyl)ureido]phenyl}carbamic acid tert-butyl ester 、 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67%的产率得到2-{4-[3-(4-tert-butoxycarbonylaminophenyl)ureido]phenylimino}imidazolidine-1,3-dicarboxylic acid di-tert-butyl ester
  参考文献：
  名称：

  Asymmetrical Diaromatic Guanidinium/2-Aminoimidazolinium Derivatives: Synthesis and DNA Affinity

  摘要：

  In this paper we report the synthesis of three families of new amidine-based aromatic derivatives as potential DNA minor groove binding agents for the treatment of cancer. The preparation of monoguanidine, mono-2-aminoimidazoline, and asymmetric diphenylguanidine/2-aminoimidazoline derivatives (compounds 1a-c to 8a-c) is presented. The affinity of these substrates and of a family of mono- and bis-isoureas (previously prepared in Rozas' laboratory) for DNA was evaluated by means of DNA thermal denaturation measurements. In particular, compounds 2c, 5c, 6c, 7c, and 8c were found to bind strongly both to natural DNA and to adenine-thymine oligonucleotides, showing a preference for the adenine-thymine base pair sequences.

  DOI：

  10.1021/jm901017t