N,N-dipropargyl-adamantan-1-amine | 3717-36-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N,N-dipropargyl-adamantan-1-amine
• 英文别名: N,N-bis(prop-2-ynyl)adamantan-1-amine
• CAS: 3717-36-0
• 化学式: C₁₆H₂₁N
• 分子量: 227.349
• InChiKey: UCKGABXKNJPTGD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.75
• 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 、 N,N-dipropargyl-adamantan-1-amine 在 copper(I) sulfate 、 sodium ascorbate 作用下， 以 二氯甲烷 、 水 为溶剂， 以90%的产率得到2,2-{4,4-[(adamantan-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：

  金刚烷胺 、 3-溴丙炔 在 potassium carbonate 作用下， 以 异丙醇 为溶剂， 反应 5.0h， 以82%的产率得到N,N-dipropargyl-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

• Polycyclic propargylamine and acetylene derivatives as multifunctional neuroprotective agents
  作者：Frank T. Zindo、Quinton R. Barber、Jacques Joubert、Jacobus J. Bergh、Jacobus P. Petzer、Sarel F. Malan

  DOI：10.1016/j.ejmech.2014.04.039

  日期：2014.6

  The aim of this study was to design drug-like molecules with multiple neuroprotective mechanisms which would ultimately inhibit N-methyl-d-aspartate (NMDA) receptors, block L-type voltage gated calcium channels (VGCC) and inhibit apoptotic processes as well as the monoamine oxidase-B (MAO-B) enzyme in the central nervous system. These types of compounds may act as neuroprotective and symptomatic drugs

  本研究的目的是设计药物样与这将最终抑制多发性神经保护机制分子Ñ甲基d天冬氨酸（NMDA）受体，块大号型电压门控钙通道（VGCC）并抑制中枢神经系统中的凋亡过程以及单胺氧化酶B（MAO-B）酶。这些类型的化合物可作为神经疾病的保护性和对症药物，例如阿尔茨海默氏病和帕金森氏病。在设计化合物时，我们专注于雷沙吉兰和司来吉兰的结构，两种众所周知的MAO-B抑制剂和拟议的神经保护剂。基于该考虑，合成的化合物均包含缀合至各种多环笼部分的雷沙吉兰和司来吉兰的炔丙基胺官能团或其衍生物。这些多环部分是非极性的，已被证明可以帮助共轭化合物跨血脑屏障转运，以及细胞膜，并具有继发性积极的神经保护作用。所有新颖的合成多环衍生物均被证明具有显着的抗凋亡活性（p  <0.05），与阳性对照司来吉兰相当。四种化合物（12，15和16）表现出有前途的VGCC和NMDA受体通道的抑制活性范围从18％到微摩尔浓度为59％和相比
• Synthesis and Structural Analysis of Novel Neuroprotective Pentacyclo[5.4.1.02,6.03,10.05,9]undecane- and Adamantane-Derived Propargylamines
  作者：Jacques Joubert、Halima Samsodien、Quinton R. Baber、Dyanne L. Cruickshank、Mino R. Caira、Sarel F. Malan

  DOI：10.1007/s10870-014-0501-y

  日期：2014.4

  pentacyclo[5.4.1.02,6.03,10.05,9]undecane and adamantane propargylamine hybrid molecules. The structural characterization of these compounds was performed using MS, FT-IR and NMR spectroscopy in combination with X-ray diffraction analysis. The single crystal X-ray analyses of four synthons (6, 8–10) are presented; 8-(N)-propargylamino-8,11-oxapentacyclo-[5.4.1.02,6.03,10.05.9]undecane (compound 6 crystallized

  在本文中，我们对新型多环五环[5.4.1.02,6.03,10.05,9]十一烷和金刚烷炔丙基胺杂化分子进行了详细的结构研究。这些化合物的结构表征是使用 MS、FT-IR 和 NMR 光谱结合 X 射线衍射分析进行的。介绍了四种合成子 (6, 8-10) 的单晶 X 射线分析；8-(N)-propargylamino-8,11-oxapentacyclo-[5.4.1.02,6.03,10.05.9]undecane（化合物6在单斜晶系中结晶，晶胞参数：a = 20.737(2) Å；b = 8.127 (1) Å；c = 12.606 (1) Å；β = 92.360(2)°；V = 2122.8(3) Å3；Z = 8)；11-羟基-(N)-炔丙基-8,11-氮杂五环[5.4.1.02,6.03,10.05.9]十一烷（化合物8在单斜晶系中结晶，晶胞参数：a = 7.9624(6) Å；b
• 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.