1-amino-17-(N1,N2-bis(tert-butoxycarbonyl)-N1-(methylcyclopropyl)guanidine)-9-azaheptadecane | 1176817-90-5

• 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: 1-amino-17-(N1,N2-bis(tert-butoxycarbonyl)-N1-(methylcyclopropyl)guanidine)-9-azaheptadecane
• 英文别名: tert-butyl N-[N'-[8-(8-aminooctylamino)octyl]-N-[(2-methylpropan-2-yl)oxycarbonyl]carbamimidoyl]-N-(cyclopropylmethyl)carbamate
• CAS: 1176817-90-5
• 化学式: C₃₁H₆₁N₅O₄
• 分子量: 567.856
• InChiKey: XETPFAKIJPQOTJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  40
• 可旋转键数：
  25
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  118
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-amino-17-(N1,N2-bis(tert-butoxycarbonyl)-N1-(methylcyclopropyl)guanidine)-9-azaheptadecane 、 N,N'-Di-Boc-N''-triflylguanidine 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以80%的产率得到1-(N1,N2-bis(tert-butoxycarbonyl)guanidine)-17-(N1,N2-bis(tert-butoxycarbonyl)-N1-(methylcyclopropyl)guanidine)-9-azaheptadecane
  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：

  在 盐酸 、 palladium 10% on activated carbon 、 氢气 作用下， 以 水 、 异丙醇 为溶剂， 反应 4.0h， 生成 1-amino-17-(N1,N2-bis(tert-butoxycarbonyl)-N1-(methylcyclopropyl)guanidine)-9-azaheptadecane
  参考文献：
  名称：

  Synthesis of linear and cyclic guazatine derivatives endowed with antibacterial activity

  摘要：

  Antibiotic resistance has reached alarming levels in many clinically-relevant human pathogens, and there is an increasing clinical need for new antibiotics active on drug-resistant Gram-negative pathogens who rapidly evolve towards pandrug resistance phenotypes. Here, we report on two related classes of guanidinic compounds endowed with antibacterial activity. The two best compounds (9a and 13d) exhibited the most potent antibacterial activity with MIC values ranging 0.12-8 mu g/ml with most tested pathogens, including both Gram-positive and Gram-negative bacteria. Interestingly, MIC values were not affected (1-8 mu g/ml) when measured using recent clinical isolates with various antibiotic resistance determinants. The results reported herein identify guazatine derivatives as an interesting starting point for the optimization of a potentially novel class of antibacterial agents. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.09.081