3,5-dimethyl-N,N-di(prop-2-yn-1-yl)adamantan-1-amine | 1239017-68-5

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 3,5-dimethyl-N,N-di(prop-2-yn-1-yl)adamantan-1-amine
• 英文别名: 3,5-di-methyl-N,N-di(prop-2-yn-1-yl)adamantan-1-amine；3,5-dimethyl-N,N-bis(prop-2-ynyl)adamantan-1-amine
• CAS: 1239017-68-5
• 化学式: C₁₈H₂₅N
• 分子量: 255.403
• InChiKey: GVLAGUWYMOIYHL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-叠氮基-1-(10H-吩噻嗪-10-基)乙酮 、 3,5-dimethyl-N,N-di(prop-2-yn-1-yl)adamantan-1-amine 在 copper(I) sulfate 、 sodium ascorbate 作用下， 以 二氯甲烷 、 水 为溶剂， 以89%的产率得到2,2-{4,4-[(3,5-dimethyladamantan-1-ylazanediyl)-bis(methylene)]bis(1H-1,2,3-triazole-4,1-diyl)}bis[1-(10H-phenothiazin-10-yl)ethanone]
  参考文献：
  名称：

  N,N-Di(prop-2-yn-1-yl)adamantan-1-amines in 1,3-Dipolar Cycloaddition Reactions with Azide-Containing Pharmacophores

  摘要：

  A synthetic approach to combining pharmacophore ligands with an aminoadamantyl-containing spacer based on a copper-catalyzed alkyne-azide 1,3-dipolar cycloaddition of N,N-di(prop-2-yne-1-yl)adamantan-1-amines and azido-containing carbazole, tetrahydrocarbazole, phenothiazine and adamantan-2-amine derivatives was proposed.

  DOI：

  10.1134/s1070363219080280
• 作为产物：
  描述：

  3,5-二甲基金刚胺 、 3-溴丙炔 在 potassium carbonate 作用下， 以 异丙醇 为溶剂， 反应 5.0h， 以84%的产率得到3,5-dimethyl-N,N-di(prop-2-yn-1-yl)adamantan-1-amine
  参考文献：
  名称：

  通过铜催化的炔-叠氮化物 1,3-偶极环加成与氨基金刚烷共轭

  摘要：

  提出了通过铜催化的炔-叠氮化物 1,3-偶极环加成与含 1,2,3-三唑和二三唑间隔物的氨基金刚烷共轭的四种变体。

  DOI：

  10.1007/s11172-018-2231-3

文献信息

• NEUROPROTECTIVE MULTIFUNCTIONAL COMPOUNDS AND PHARMACEUTICAL COMPOSITIONS COMPRISING THEM
  申请人：Youdim Moussa B. H.

  公开号：US20120040993A1

  公开（公告）日：2012-02-16

  Multifunctional compounds are provided, comprising two or more functional moieties selected from: (i) a moiety that imparts an iron chelator function; (ii) a moiety that imparts a neuroprotective function; (iii) a moiety that imparts combined antiapoptotic, neuroprotective and/or neurorestorative functions; (iv) a moiety that imparts brain MAO inhibition, preferably with little or no MAO inhibition in liver and small intestine; (v) a moiety that imparts cholinesterase inhibitory function; and (vi) a moiety that imparts an N-methyl-D-aspartic acid receptor (NMDAR) inhibition, and pharmaceutically acceptable salts and optical isomers thereof. The multifunctional compounds are useful in the treatment or prevention of diseases, disorders or conditions that can be prevented and/or treated by iron chelation therapy, and/or neuroprotection and/or neurorestoration, and/or apoptosis inhibition and/or MAO inhibition and/or cholinesterase inhibition and/or NMADR inhibition. The present invention encompasses compounds of the formulas I to VI.

  提供了多功能化合物，包括从以下选择的两个或多个官能团：(i)赋予铁螯合剂功能的官能团；(ii)赋予神经保护功能的官能团；(iii)赋予联合抗凋亡、神经保护和/或神经修复功能的官能团；(iv)赋予大脑MAO抑制作用的官能团，优选在肝脏和小肠中几乎没有或没有MAO抑制作用；(v)赋予胆碱酯酶抑制作用的官能团；(vi)赋予N-甲基-D-天门冬氨酸受体(NMDAR)抑制作用的官能团，以及其药学上可接受的盐和光学异构体。这些多功能化合物在预防和/或治疗可以通过铁螯合疗法、神经保护和/或神经修复、凋亡抑制和/或MAO抑制和/或胆碱酯酶抑制和/或NMDAR抑制来预防和/或治疗的疾病、疾病或状况中是有用的。本发明涵盖了公式I至VI的化合物。
• US8802675B2
  申请人：——

  公开号：US8802675B2

  公开（公告）日：2014-08-12
• [EN] NEUROPROTECTIVE MULTIFUNCTIONAL COMPOUNDS AND PHARMACEUTICAL COMPOSITIONS COMPRISING THEM<br/>[FR] COMPOSÉS MULTIFONCTIONNELS NEUROPROTECTEURS ET COMPOSITIONS PHARMACEUTIQUES LES COMPRENANT
  申请人：YEDA RES & DEV

  公开号：WO2010086860A2

  公开（公告）日：2010-08-05

  Multifunctional compounds are provided, comprising two or more functional moieties selected from: (i) a moiety that imparts an iron chelator function; (ii) a moiety that imparts a neuroprotective function; (iii) a moiety that imparts combined antiapoptotic, neuroprotective and/or neurorestorative functions; (iv) a moiety that imparts brain MAO inhibition, preferably with little or no MAO inhibition in liver and small intestine; (v) a moiety that imparts cholinesterase inhibitory function; and (vi) a moiety that imparts an N-methyl-D-aspartic acid receptor (NMDAR) inhibition, and pharmaceutically acceptable salts and optical isomers thereof. The multifunctional compounds are useful in the treatment or prevention of diseases, disorders or conditions that can be prevented and/or treated by iron chelation therapy, and/or neuroprotection and/or neurorestoration, and/or apoptosis inhibition and/or MAO inhibition and/or cholinesterase inhibition and/or NMADR inhibition. The present invention encompasses compounds of the formulas I to Vl.
• Conjugation of aminoadamantanes by copper-catalyzed alkyne-azide 1,3-dipolar cycloaddition
  作者：V. B. Sokolov、A. Yu. Aksinenko、T. A. Epishina、T. V. Goreva

  DOI：10.1007/s11172-018-2231-3

  日期：2018.8

  Four variants of conjugation of aminoadamantanes with 1,2,3-triazole- and ditriazolecontaining spacers by copper-catalyzed alkyne-azide 1,3-dipolar cycloaddition of azido- and propargyl-containing aminoadamantanes were suggested.

  提出了通过铜催化的炔-叠氮化物 1,3-偶极环加成与含 1,2,3-三唑和二三唑间隔物的氨基金刚烷共轭的四种变体。
• N,N-Di(prop-2-yn-1-yl)adamantan-1-amines in 1,3-Dipolar Cycloaddition Reactions with Azide-Containing Pharmacophores
  作者：V. B. Sokolov、A. Yu. Aksinenko

  DOI：10.1134/s1070363219080280

  日期：2019.8

  A synthetic approach to combining pharmacophore ligands with an aminoadamantyl-containing spacer based on a copper-catalyzed alkyne-azide 1,3-dipolar cycloaddition of N,N-di(prop-2-yne-1-yl)adamantan-1-amines and azido-containing carbazole, tetrahydrocarbazole, phenothiazine and adamantan-2-amine derivatives was proposed.