N-(3-methyl-2-oxaadamant-1-yl)cyclohexanecarboxamide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: N-(3-methyl-2-oxaadamant-1-yl)cyclohexanecarboxamide
• 英文别名: N-(3-methyl-2-oxatricyclo[3.3.1.13,7]decan-1-yl)cyclohexanecarboxamide
• 化学式: C₁₇H₂₇NO₂
• 分子量: 277.407
• InChiKey: ATRFABKLQGZRGA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-methyl-2-oxaadamantane-1-amine hydrochloride 、 环己甲酸 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 乙酸乙酯 为溶剂， 以39%的产率得到N-(3-methyl-2-oxaadamant-1-yl)cyclohexanecarboxamide
  参考文献：
  名称：

  Novel 11β-HSD1 inhibitors: C-1 versus C-2 substitution and effect of the introduction of an oxygen atom in the adamantane scaffold

  摘要：

  The adamantane scaffold is found in several marketed drugs and in many investigational 11 beta-HSD1 inhibitors. Interestingly, all the clinically approved adamantane derivatives are C-1 substituted. We demonstrate that, in a series of paired adamantane isomers, substitution of the adamantane in C-2 is preferred over the substitution at C-1 and is necessary for potency at human 11 beta-HSD1. Furthermore, the introduction of an oxygen atom in the hydrocarbon scaffold of adamantane is deleterious to 11 beta-HSD1 inhibition. Molecular modeling studies provide a basis to rationalize these features. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.07.097

文献信息

• Novel 11β-HSD1 inhibitors: C-1 versus C-2 substitution and effect of the introduction of an oxygen atom in the adamantane scaffold
  作者：Rosana Leiva、Constantí Seira、Andrew McBride、Margaret Binnie、F. Javier Luque、Axel Bidon-Chanal、Scott P. Webster、Santiago Vázquez

  DOI：10.1016/j.bmcl.2015.07.097

  日期：2015.10

  The adamantane scaffold is found in several marketed drugs and in many investigational 11 beta-HSD1 inhibitors. Interestingly, all the clinically approved adamantane derivatives are C-1 substituted. We demonstrate that, in a series of paired adamantane isomers, substitution of the adamantane in C-2 is preferred over the substitution at C-1 and is necessary for potency at human 11 beta-HSD1. Furthermore, the introduction of an oxygen atom in the hydrocarbon scaffold of adamantane is deleterious to 11 beta-HSD1 inhibition. Molecular modeling studies provide a basis to rationalize these features. (C) 2015 Elsevier Ltd. All rights reserved.