4-[N2,N3-bis(tert-butoxycarbonyl)-N3-(γ,γ-dimethylallyl)guanidine]-1-[N5,N6-bis(tert-butoxycarbonyl)guanidino]butane | 1176817-60-9

• 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: 4-[N2,N3-bis(tert-butoxycarbonyl)-N3-(γ,γ-dimethylallyl)guanidine]-1-[N5,N6-bis(tert-butoxycarbonyl)guanidino]butane
• 英文别名: tert-butyl N-[N'-[4-[bis[(2-methylpropan-2-yl)oxycarbonylamino]methylideneamino]butyl]-N-[(2-methylpropan-2-yl)oxycarbonyl]carbamimidoyl]-N-(3-methylbut-2-enyl)carbamate
• CAS: 1176817-60-9
• 化学式: C₃₁H₅₆N₆O₈
• 分子量: 640.821
• InChiKey: BKJXPUIRFOBBSO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  45
• 可旋转键数：
  19
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  169
• 氢给体数：
  3
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  N,N'-bis-Boc-S-methyl-isothiourea 、 4-2,N³-bis(tert-butoxycarbonyl)-N³-(γ,γ-dimethylallyl)guanidino>-1-aminobutane 以 四氢呋喃 为溶剂， 反应 16.0h， 以0.625 g的产率得到4-[N2,N3-bis(tert-butoxycarbonyl)-N3-(γ,γ-dimethylallyl)guanidine]-1-[N5,N6-bis(tert-butoxycarbonyl)guanidino]butane
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Guanidino Compounds Endowed with Subnanomolar Affinity as Competitive Inhibitors of Maize Polyamine Oxidase

  摘要：

  Previous studies on agmatine and its derivatives suggested that the presence of hydrophobic groups on the guanidine moiety was a crucial key for inhibitory activity of maize polyamine oxidase. Accordingly, new lipophilic agmatine and iminoctadine derivatives were synthesized and tested for their ability to inhibit this enzyme. Several compounds showed an affinity in the nanomolar range, while a cyclopropylmethyl derivative of iminoctadine was found to be the most potent inhibitor of maize polyamine oxidase reported so far (K-i = 0.08 nM).

  DOI：

  10.1021/jm900371z

文献信息

• Synthesis and Biological Evaluation of Guanidino Compounds Endowed with Subnanomolar Affinity as Competitive Inhibitors of Maize Polyamine Oxidase
  作者：Fabrizio Manetti、Alessandra Cona、Lucilla Angeli、Claudia Mugnaini、Francesco Raffi、Caterina Capone、Elena Dreassi、Alessandra Tania Zizzari、Alessandra Tisi、Rodolfo Federico、Maurizio Botta

  DOI：10.1021/jm900371z

  日期：2009.8.13

  Previous studies on agmatine and its derivatives suggested that the presence of hydrophobic groups on the guanidine moiety was a crucial key for inhibitory activity of maize polyamine oxidase. Accordingly, new lipophilic agmatine and iminoctadine derivatives were synthesized and tested for their ability to inhibit this enzyme. Several compounds showed an affinity in the nanomolar range, while a cyclopropylmethyl derivative of iminoctadine was found to be the most potent inhibitor of maize polyamine oxidase reported so far (K-i = 0.08 nM).