1-(adamantan-1-ylmethyl)-2-cyano-3-(3-fluorobenzyl)guanidine

• 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: 1-(adamantan-1-ylmethyl)-2-cyano-3-(3-fluorobenzyl)guanidine
• 英文别名: 1-(1-Adamantylmethyl)-3-cyano-2-[(3-fluorophenyl)methyl]guanidine；1-(1-adamantylmethyl)-3-cyano-2-[(3-fluorophenyl)methyl]guanidine
• 化学式: C₂₀H₂₅FN₄
• 分子量: 340.444
• InChiKey: MZSHJRMXIAPGID-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  60.2
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-氟苄胺 、 phenyl N-((adamantan-1-yl)methyl)-N'-cyanocarbamimidate 以 二氯甲烷 、 乙酸乙酯 、 异丙醇 为溶剂， 以33%的产率得到1-(adamantan-1-ylmethyl)-2-cyano-3-(3-fluorobenzyl)guanidine
  参考文献：
  名称：

  Discovery and pharmacological evaluation of a novel series of adamantyl cyanoguanidines as P2X7 receptor antagonists

  摘要：

  Here we report adamantyl cyanoguanidine compounds based on hybrids of the adamantyl amide scaffold reported by AstraZeneca and cyanoguanidine scaffold reported by Abbott Laboratories. Compound 27 displayed five-fold greater inhibitory potency than the lead compound 2 in both pore-formation and interleukin-1 beta release assays, while 35-treated mice displayed an antidepressant phenotype in behavioral studies. This SAR study provides a proof of concept for hybrid compounds, which will help in the further development of P2X(7)R antagonists. (C) 2017 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2017.02.060

文献信息

• Discovery and pharmacological evaluation of a novel series of adamantyl cyanoguanidines as P2X7 receptor antagonists
  作者：James O'Brien-Brown、Alexander Jackson、Tristan A. Reekie、Melissa L. Barron、Eryn L. Werry、Paolo Schiavini、Michelle McDonnell、Lenka Munoz、Shane Wilkinson、Benjamin Noll、Shudong Wang、Michael Kassiou

  DOI：10.1016/j.ejmech.2017.02.060

  日期：2017.4

  Here we report adamantyl cyanoguanidine compounds based on hybrids of the adamantyl amide scaffold reported by AstraZeneca and cyanoguanidine scaffold reported by Abbott Laboratories. Compound 27 displayed five-fold greater inhibitory potency than the lead compound 2 in both pore-formation and interleukin-1 beta release assays, while 35-treated mice displayed an antidepressant phenotype in behavioral studies. This SAR study provides a proof of concept for hybrid compounds, which will help in the further development of P2X(7)R antagonists. (C) 2017 Elsevier Masson SAS. All rights reserved.