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N-[(4-aminophenyl)methyl]adamantane-1-carboxamide | 1179658-63-9

中文名称
——
中文别名
——
英文名称
N-[(4-aminophenyl)methyl]adamantane-1-carboxamide
英文别名
——
N-[(4-aminophenyl)methyl]adamantane-1-carboxamide化学式
CAS
1179658-63-9
化学式
C18H24N2O
mdl
——
分子量
284.401
InChiKey
FDNAFJGQSOAZIJ-UHFFFAOYSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

计算性质

  • 辛醇/水分配系数(LogP):
    2.9
  • 重原子数:
    21
  • 可旋转键数:
    3
  • 环数:
    5.0
  • sp3杂化的碳原子比例:
    0.61
  • 拓扑面积:
    55.1
  • 氢给体数:
    2
  • 氢受体数:
    2

上下游信息

  • 下游产品
    中文名称 英文名称 CAS号 化学式 分子量

反应信息

  • 作为反应物:
    描述:
    参考文献:
    名称:
    Structure–activity relationships of substituted oxyoxalamides as inhibitors of the human soluble epoxide hydrolase
    摘要:
    We explored both structure-activity relationships among substituted oxyoxalamides used as the primary pharmacophore of inhibitors of the human sEH and as a secondary pharmacophore to improve water solubility of inhibitors. When the oxyoxalamide function was modified with a variety of alkyls or substituted alkyls, compound 6 with a 2-adamantyl group and a benzyl group was found to be a potent sEH inhibitor, suggesting that the substituted oxyoxalamide function is a promising primary pharmacophore for the human sEH, and compound 6 can be a novel lead structure for the development of further improved oxyoxalamide or other related derivatives. In addition, introduction of substituted oxyoxalamide to inhibitors with an amide or urea primary pharmacophore produced significant improvements in inhibition potency and water solubility. In particular, the N,N,O-trimethyloxyoxalamide group in amide or urea inhibitors (26 and 31) was most effective among those tested for both inhibition and solubility. The results indicate that substituted oxyoxalamide function incorporated into amide or urea inhibitors is a useful secondary pharmacophore, and the resulting structures will be an important basis for the development of bioavailable sEH inhibitors. (C) 2013 Elsevier Ltd. All rights reserved.
    DOI:
    10.1016/j.bmc.2013.12.027
  • 作为产物:
    描述:
    1-金刚烷甲酸4-氨基苄胺4-二甲氨基吡啶盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下, 以 二氯甲烷 为溶剂, 以95%的产率得到N-[(4-aminophenyl)methyl]adamantane-1-carboxamide
    参考文献:
    名称:
    酰胺-膦酸酯衍生物作为人类可溶性环氧化物水解酶抑制剂的构效关系。
    摘要:
    研究了作为人类可溶性环氧水解酶(sEH)抑制剂的酰胺-膦酸酯衍生物的构效关系。首先,将一系列烷基或芳基基团在碳原子α上取代为酰胺化合物中的膦酸酯官能团,以查看取代的膦酸酯是否可以充当次级药效团。发现α碳上的叔丁基(16)对目标酶产生最有效的抑制作用。其他取代基(如芳基,取代的芳基,环烷基和烷基)诱导抑制作用降低4-50倍。然后,O-取代基在膦酸酯官能团上的修饰表明,二乙基(16和23)对于抑制其他更长的烷基或取代的烷基是优选的。在具有优化的二乙基膦酸酯部分和烷基取代的酰胺化合物(如金刚烷(16),四氢萘(31)或金刚烷甲烷(36))中,获得了高度有效的抑制作用。另外,所得的有效的酰胺-膦酸酯化合物具有合理的水溶性,这表明酰胺抑制剂中的取代的膦酸酯对于抑制人sEH的效力和作为辅助药效团的水溶性均是有效的。
    DOI:
    10.1016/j.bmc.2015.10.016
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文献信息

  • Structure–activity relationships of amide–phosphonate derivatives as inhibitors of the human soluble epoxide hydrolase
    作者:In-Hae Kim、Yong-Kyu Park、Hisashi Nishiwaki、Bruce D. Hammock、Kosuke Nishi
    DOI:10.1016/j.bmc.2015.10.016
    日期:2015.11
    alkyl or aryl groups were substituted on the carbon alpha to the phosphonate function in amide compounds to see whether substituted phosphonates can act as a secondary pharmacophore. A tert-butyl group (16) on the alpha carbon was found to yield most potent inhibition on the target enzyme. A 4-50-fold drop in inhibition was induced by other substituents such as aryls, substituted aryls, cycloalkyls, and
    研究了作为人类可溶性环氧水解酶(sEH)抑制剂的酰胺-膦酸酯衍生物的构效关系。首先,将一系列烷基或芳基基团在碳原子α上取代为酰胺化合物中的膦酸酯官能团,以查看取代的膦酸酯是否可以充当次级药效团。发现α碳上的叔丁基(16)对目标酶产生最有效的抑制作用。其他取代基(如芳基,取代的芳基,环烷基和烷基)诱导抑制作用降低4-50倍。然后,O-取代基在膦酸酯官能团上的修饰表明,二乙基(16和23)对于抑制其他更长的烷基或取代的烷基是优选的。在具有优化的二乙基膦酸酯部分和烷基取代的酰胺化合物(如金刚烷(16),四氢萘(31)或金刚烷甲烷(36))中,获得了高度有效的抑制作用。另外,所得的有效的酰胺-膦酸酯化合物具有合理的水溶性,这表明酰胺抑制剂中的取代的膦酸酯对于抑制人sEH的效力和作为辅助药效团的水溶性均是有效的。
  • Structure–activity relationships of substituted oxyoxalamides as inhibitors of the human soluble epoxide hydrolase
    作者:In-Hae Kim、In-Hee Lee、Hisashi Nishiwaki、Bruce D. Hammock、Kosuke Nishi
    DOI:10.1016/j.bmc.2013.12.027
    日期:2014.2
    We explored both structure-activity relationships among substituted oxyoxalamides used as the primary pharmacophore of inhibitors of the human sEH and as a secondary pharmacophore to improve water solubility of inhibitors. When the oxyoxalamide function was modified with a variety of alkyls or substituted alkyls, compound 6 with a 2-adamantyl group and a benzyl group was found to be a potent sEH inhibitor, suggesting that the substituted oxyoxalamide function is a promising primary pharmacophore for the human sEH, and compound 6 can be a novel lead structure for the development of further improved oxyoxalamide or other related derivatives. In addition, introduction of substituted oxyoxalamide to inhibitors with an amide or urea primary pharmacophore produced significant improvements in inhibition potency and water solubility. In particular, the N,N,O-trimethyloxyoxalamide group in amide or urea inhibitors (26 and 31) was most effective among those tested for both inhibition and solubility. The results indicate that substituted oxyoxalamide function incorporated into amide or urea inhibitors is a useful secondary pharmacophore, and the resulting structures will be an important basis for the development of bioavailable sEH inhibitors. (C) 2013 Elsevier Ltd. All rights reserved.
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