N1,N2-bis(tert-butoxycarbonyl)-N1-(cyclohexylethyl)-S-methylisothiourea | 1176817-68-7

• 分子结构分类: 有机化合物
• 英文名称: N1,N2-bis(tert-butoxycarbonyl)-N1-(cyclohexylethyl)-S-methylisothiourea
• 英文别名: tert-butyl N-(2-cyclohexylethyl)-N-[N-[(2-methylpropan-2-yl)oxycarbonyl]-C-methylsulfanylcarbonimidoyl]carbamate
• CAS: 1176817-68-7
• 化学式: C₂₀H₃₆N₂O₄S
• 分子量: 400.583
• InChiKey: IQPXFQPHMQIGHJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.85
• 重原子数：
  27.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  68.2
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  N1,N2-bis(tert-butoxycarbonyl)-N1-(cyclohexylethyl)-S-methylisothiourea 、 N-(5-氨基戊基)氨基甲酸叔丁酯 以 四氢呋喃 为溶剂， 反应 18.0h， 以95%的产率得到(N1-5-aminopentyl)-N3-(cyclohexylethyl)-N1,N2,N3-tris(tert-butoxycarbonyl)guanidine
  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
• 作为产物：
  描述：

  2-环己基乙醇 、 N,N'-bis-Boc-S-methyl-isothiourea 在 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 以95%的产率得到N1,N2-bis(tert-butoxycarbonyl)-N1-(cyclohexylethyl)-S-methylisothiourea
  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