N-(adamantan-1-yl)-5-(dimethylamino)-1-naphthalenesulfonamide

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-(adamantan-1-yl)-5-(dimethylamino)-1-naphthalenesulfonamide
• 英文别名: N-(1-adamantyl)-5-(dimethylamino)naphthalene-1-sulfonamide
• 化学式: C₂₂H₂₈N₂O₂S
• 分子量: 384.543
• InChiKey: GUPDTGYUVIQZLD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  57.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  丹酰氯 、 盐酸金刚烷胺 在 三乙胺 作用下， 以 氯仿 为溶剂， 反应 48.0h， 以35%的产率得到N-(adamantan-1-yl)-5-(dimethylamino)-1-naphthalenesulfonamide
  参考文献：
  名称：

  Synthesis and evaluation of fluorescent heterocyclic aminoadamantanes as multifunctional neuroprotective agents

  摘要：

  A series of fluorescent heterocyclic adamantane amines were synthesised with the goal to develop novel fluorescent ligands for neurological assay development. These derivatives demonstrated multifunctional neuroprotective activity through inhibition of the N-methyl-D-aspartate receptor/ion channel, calcium channels and the enzyme nitric oxide synthase. It also exhibited a high degree of free radical scavenging potential. N-(1-adamantyl)-2-oxo-chromene-3-carboxamide (8), N-adamantan-1-yl-5-dimethyl-amino-1-naphthalenesulfonic acid (11) and N-(1-cyano-2H-isoindol-2-yl) adamantan-1-amine (12) were found to possess a high degree of multifunctionality with favourable physical-chemical properties for bioavailability and blood-brain barrier permeability. The ability of these heterocyclic adamantane amine derivatives as nitric oxide synthase inhibitors, calcium channel modulators, NMDAR inhibitors and effective antioxidants, indicate that they may find application as multifunctional drugs in neuroprotection. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.05.034

文献信息

• Synthesis and evaluation of fluorescent heterocyclic aminoadamantanes as multifunctional neuroprotective agents
  作者：Jacques Joubert、Sandra van Dyk、Ivan R. Green、Sarel F. Malan

  DOI：10.1016/j.bmc.2011.05.034

  日期：2011.7

  A series of fluorescent heterocyclic adamantane amines were synthesised with the goal to develop novel fluorescent ligands for neurological assay development. These derivatives demonstrated multifunctional neuroprotective activity through inhibition of the N-methyl-D-aspartate receptor/ion channel, calcium channels and the enzyme nitric oxide synthase. It also exhibited a high degree of free radical scavenging potential. N-(1-adamantyl)-2-oxo-chromene-3-carboxamide (8), N-adamantan-1-yl-5-dimethyl-amino-1-naphthalenesulfonic acid (11) and N-(1-cyano-2H-isoindol-2-yl) adamantan-1-amine (12) were found to possess a high degree of multifunctionality with favourable physical-chemical properties for bioavailability and blood-brain barrier permeability. The ability of these heterocyclic adamantane amine derivatives as nitric oxide synthase inhibitors, calcium channel modulators, NMDAR inhibitors and effective antioxidants, indicate that they may find application as multifunctional drugs in neuroprotection. (C) 2011 Elsevier Ltd. All rights reserved.