1,3-Dimethyl-5-aminomethyladamantane | 110894-15-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 1,3-Dimethyl-5-aminomethyladamantane
• 英文别名: 3.5-Dimethyl-1-adamantanmethylamin；(3,8-Dimethyladamantanyl)methylamine；(3,5-dimethyl-1-adamantyl)methanamine
• CAS: 110894-15-0
• 化学式: C₁₃H₂₃N
• mdl: MFCD02208132
• 分子量: 193.332
• InChiKey: GPYYBGAAAREIRT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  26
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1,3-Dimethyl-5-aminomethyladamantane 在 三乙胺 作用下， 以 甲醇 为溶剂， 生成 N-[(3,5-二甲基金刚烷-1-基)甲基]乙胺
  参考文献：
  名称：

  The synthesis and radioprotective activity of acetamidine thiophosphoric acid derivatives

  摘要：

  DOI：

  10.1007/bf00778855
• 作为产物：
  描述：

  3,5-dimethyladamantane-1-carboxamide 在 lithium aluminium tetrahydride 、 氯化亚砜 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 8.0h， 生成 1,3-Dimethyl-5-aminomethyladamantane
  参考文献：
  名称：

  脂环族单胺和二胺盐酸盐的合成及抗病毒活性

  摘要：

  大量出版物致力于研究脂环族衍生物的抗病毒活性 [2, 4, 5, 7]。给定类别的抗病毒制剂，例如盐酸米丹坦L-氨基金刚烷和盐酸金刚烷胺a-甲基1-氨基甲基金刚烷最近在医学中得到了广泛应用。在这方面，合成和研究金刚烷、1,3-二甲基金刚烷和双环[2.2.1]庚烷系列的单胺和二胺盐酸盐的抗病毒活性是很有意义的。

  DOI：

  10.1007/bf00767400

文献信息

• [EN] NOVEL ADAMANTANE AND MEMANTINE DERIVATIVES AS PERIPHERAL NMDA RECEPTOR ANTAGONISTS<br/>[FR] NOUVEAUX DÉRIVÉS ADAMANTANE ET MÉMANTINE UTILISÉS COMME ANTAGONISTES PÉRIPHÉRIQUES DES RÉCEPTEUR NMDA
  申请人：INSERM (INSTITUT NAT DE LA SANTÉ ET DE LA RECH MÉDICALE)

  公开号：WO2017017116A1

  公开（公告）日：2017-02-02

  The present invention relates to cationic compounds of formula (I) for use as peripheral NMDA receptor antagonists.

  本发明涉及公式（I）的阳离子化合物，用作外周NMDA受体拮抗剂。
• Search for Selective Glua1 Ampa Receptor Antagonists in a Series of Dicationic Compounds
  作者：V. E. Gmiro、A. S. Zhigulin

  DOI：10.1007/s11094-022-02635-w

  日期：2022.6

  Homologous series of dicationic derivatives based on adamantyl and phenylcyclohexyl fragments in which the cationic groups and the distance between them were varied by using hydrocarbon chains five or six methylene units in length were synthesized. The ability of the dications to block open channels of NMDA and AMPA glutamate receptors was investigated. Pyramidal neurons isolated from the hippocampal CA1 zone were used to study the NMDA channels. Giant cholinergic interneurons of striatum were used in studies of AMPA receptors missing GluA2 subunits. An investigation of the structure—activity relationship of the dications revealed five compounds (IEM-2131, -2132, -2133, -2041, -2297) that surpassed the reference GluA1 AMPA antagonist IEM-1460 in terms of GluA1 AMPA selectivity. IEM-2131, which was an order of magnitude more active than IEM-1460 in AMPA-blocking activity (IC50 = 0.29 and 3 μM, respectively), showed the maximum AMPA activity and selectivity and had five times better AMPA selectivity (101- and 500-fold, respectively). The clinical prospects of the new GluA1 AMPA blockers were discussed.

  基于金刚烷和苯基环己烷片段，通过合成长度为5或6个亚甲基单元的烃链，我们获得了阳离子基团及其间距各异的同源二阳离子衍生物系列。我们研究了二阳离子阻断NMDA和AMPA谷氨酸受体开放通道的能力。从海马CA1区分离出的锥体神经元被用于研究NMDA通道。纹状体中的巨大型胆碱能中间神经元被用于研究缺失GluA2亚基的AMPA受体。对二阳离子的结构-活性关系的研究表明，有五种化合物（IEM-2131、-2132、-2133、-2041、-2297）在GluA1 AMPA选择性方面超过了参考GluA1 AMPA拮抗剂IEM-1460。IEM-2131在AMPA阻断活性（IC50分别为0.29和3μM）方面比IEM-1460高出一个数量级，显示出最大的AMPA活性和选择性，并且AMPA选择性提高了5倍（分别为101倍和500倍）。我们讨论了新型GluA1 AMPA阻断剂的临床前景。
• 2-Mercaptoacetamidine and derivatives as antiradiation agents
  作者：Roger D. Westland、Mary M. Merz、Susan M. Alexander、Linda S. Newton、Ludwig Bauer、Terry T. Conway、Jerry M. Barton、Krishan K. Khullar、Prabhakar B. Devdhar、Marie M. Grenan

  DOI：10.1021/jm00282a027

  日期：1972.12
• NOVEL ADAMANTANE AND MEMANTINE DERIVATIVES AS PERIPHERAL NMDA RECEPTOR ANTAGONISTS
  申请人：INSERM - Institut National de la Santé et de la Recherche Médicale

  公开号：EP3328826A1

  公开（公告）日：2018-06-06
• SCREENING METHODS FOR AMYLOID BETA MODULATORS
  申请人：Slon-Usakiewicz Jacek

  公开号：US20110028719A1

  公开（公告）日：2011-02-03

  The present invention relates to methods for screening, identifying, and/or quantifying modulators of amyloid and/or aggregates, fibrils or components thereof, in particular modulators of amyloid β-peptide (Aβ) or Aβ fibrils. Aspects of the invention provide methods for screening putative modulators against an Amyloid target, in particular an Aβ target, so as to determine which modulators bind to or interact with the target, or interfere with the interaction of an indicator agent and the target. Particular aspects of the invention employ mass spectrometric methods for the screening of an Amyloid target against compound libraries, in particular mixtures of compounds or combinatorial libraries.