N-adamantyl-propane-1,3-diamine | 46370-35-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-adamantyl-propane-1,3-diamine
• 英文别名: N-(adamantan-1-yl)propane-1,3-diamine；N-(1-Adamantyl)-1,3-propandiamin；N-(1-adamantyl)-1,3-propanediamine；3-adamantylaminopropylamine；N'-(1-adamantyl)propane-1,3-diamine
• CAS: 46370-35-8
• 化学式: C₁₃H₂₄N₂
• 分子量: 208.347
• InChiKey: PEISMEIIGOUEOP-UHFFFAOYSA-N

物化性质

• 沸点：
  302.0±10.0 °C(Predicted)
• 密度：
  1.03±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  38
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-adamantyl-propane-1,3-diamine 在 盐酸 作用下， 以 水 为溶剂， 以100%的产率得到N-(1-adamantyl)propane-1,3-diamine dihydrochloride
  参考文献：
  名称：

  理论与实验之间的纽带：应用于葫芦[n] uril·来宾结合相互作用的非经验量子力学计算方法

  摘要：

  利用DFT-D3量子力学计算方法研究了11个X射线结构训练集，用于确定葫芦[ n ] uril（CB [7或8]）宿主与金刚烷/二金刚烷铵/铵客体之间的仿生复合物G计算的结合能。这项工作的新颖之处在于，通过与更精确的方法进行比较，证明了DFT功能的BLYP-D3 / def2-TZVPP选择的保真度。对于第一次，CB [ Ñ ] ⋅客体复合物的结合能子[例如，Δ ë分散，Δ ë静电，Δ ģ溶剂化，结合熵（ - Ť ΔS），并计算出诱导拟合E变形（主体），E变形（客座）。通过使用此协议，每个复合体仅需要几周的计算时间。还通过DFT-D3方法研究了葫芦[ n ] uril（n = 5、6、7、8 ）分离的宿主分子的变形（刚度）和溶剂化特性（着重于腔的去溶剂化）。高ρ 2 Δ之间= 0.84的相关系数ģ exptl和Δ ģ计算而不计算出的术语的任何缩放（在298K）中的溶液来实现。该线性相关性用

  DOI：

  10.1002/chem.201601833
• 作为产物：
  描述：

  盐酸金刚烷胺 在 lithium aluminium tetrahydride 、 碳酸氢钠 作用下， 以 乙醚 、 水 为溶剂， 生成 N-adamantyl-propane-1,3-diamine
  参考文献：
  名称：

  Synthesis, evaluation and application of polycyclic fluorescent analogues as N-methyl-d-aspartate receptor and voltage gated calcium channel ligands

  摘要：

  A series of polycyclic fluorescent ligands were synthesised and evaluated in murine striatal synaptoneurosomes for N-methyl-D-aspartate receptor (NMDAR) mediated calcium flux inhibition and inhibition of calcium influx through voltage gated calcium channels (VGCC). Amantadine (a) and N-(1-adamantyl)-1,3-propanediamine (c) substituted with 1-cyanoisoindole (3), indazole (5), dinitrobenzene (7, 8), dansyl (9, 10) and coumarin (11) moieties showed moderate to high inhibition of the NMDAR. A high degree of VGCC inhibition was observed for the cyanoisoindole compounds (3,4) the dansyl compounds (9,10) and the coumarin compound (12). Fluorophores conjugated to hydroxy-4-aza-8-oxoheptacyclotetradecane (13, 14) did not exhibit any significant VGCC inhibition, but the indazole conjugate (14) showed promising NMDAR activity. Dose response curves were calculated for selected NMDAR inhibitors (8-11) and N-[3-(1-adamantylamino)propyl]-5-dimethylaminonaphthalene-1-sulfonamide (10) exhibited the highest activity of the novel compounds. Compound 10 was further used as a fluorescent NMDAR ligand in a fluorescent competition assay utilizing MK-801, NGP1-01 and amantadine as known NMDAR inhibitors to demonstrate the possible applications of the novel fluorescent compounds. These small molecule fluorescent ligands can be considered as possible pharmacological tools in assay development and/or other investigations in the study of neurodegeneration. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.08.008

文献信息

• Amination of chloro-substituted heteroarenes with adamantane-containing amines
  作者：A. S. Abel、O. K. Grigorova、A. D. Averin、O. A. Maloshitskaya、G. M. Butov、E. N. Savelyev、B. S. Orlinson、I. A. Novakov、I. P. Beletskaya

  DOI：10.1007/s11172-016-1516-7

  日期：2016.7

  adamantane-containing amines characterized by different steric hindrances at the amino group was studied. The yields of the amination products depended on the structure of starting compounds. In the reactions of all the dichloroheteroarenes, selective substitution of only one chlorine atom took place, with the best yields being observed for 2,6-dichloropyrazine. In the reaction of 1,3-dichloroisoquinoline

  研究了 3,6-二氯哒嗪、氯吡嗪、2,3 和 2,6-二氯吡嗪、2-氯喹喔啉、1-氯和 1,3-二氯异喹啉与各种含金刚烷胺的胺化反应，这些胺的特征在于氨基具有不同的空间位阻。胺化产物的产率取决于起始化合物的结构。在所有二氯杂芳烃的反应中，仅发生一个氯原子的选择性取代，2,6-二氯吡嗪的产率最高。在 1,3-二氯异喹啉的反应中，1 位的氯原子被选择性取代，产率高达 90%。
• Synthesis and Antiplatelet Activity of New Imidazole-4-Carboxylic Acid Derivatives
  作者：Klaus Rehse、Jens Steege

  DOI：10.1002/ardp.200500150

  日期：2005.11

  1‐Arylalkyl‐5‐phenylsulfonamino‐imidazole‐4‐carboxylic acid esters and their carboxamides with an additional secondary amino group were synthesized and identified as antiplatelet agents in a low micromolar range (Born‐test, inducer collagen). To describe the mechanism of action more precisely the Born‐test was carried out as well with ADP, adrenaline or PAF, respectively. In addition, two compounds

  合成了 1-Aryl烷基-5-苯基磺氨基-咪唑-4-羧酸酯及其带有额外仲氨基的羧酰胺，并鉴定为低微摩尔范围内的抗血小板药物（Born test，诱导胶原蛋白）。为了更准确地描述作用机制，还分别用 ADP、肾上腺素或 PAF 进行了 Born 测试。此外，研究了两种化合物的 COX-1 抑制活性。如果满足基本结构标准，即酰胺基团或酯、磺酰氨基残基、疏水部分和仲氨基官能团，轻微的结构修饰能够改变上述血小板受体之间的活性模式。因此，酯 5c 在 IC50 = 1 μM 和 COX-1 抑制 (IC50 = 0.4 μM) 下表现出 PAF 拮抗活性。甲酰胺 6c 显示出 ADP 拮抗特性 (IC50 = 2 µM)。化合物 6g 也是 PAF 拮抗剂 (IC50 = 4 μM) 和 COX-1 抑制剂 (IC50 = 1 μM)。衍生物 6i 显示出强烈的抗肾上腺素能 (IC50 = 0.15 μM)
• Catalyst-free amination of 2-fluoropyridine and 2-fluoro-5-halopyridines with adamantane amines
  作者：A. S. Abel、O. K. Grigorova、A. D. Averin、O. A. Maloshitskaya、O. A. Popov、G. M. Butov、E. N. Savelyev、B. S. Orlinson、I. A. Novakov、I. P. Beletskaya

  DOI：10.1007/s11172-015-0919-1

  日期：2015.3

  Catalyst-free reactions of 2-fluoropyridine with amines and diamines bearing the adamantyl moiety at either the N atom or in the side chain were studied. Amines, which do not contain secondary alkyl substituents at the amino group, react with an excess of 2-fluoropyridine to give N-(pyridin-2-yl) derivatives in the yields from moderate to good. 2-Fluoro-5-halopyridines were found to be more reactive

  研究了 2-氟吡啶与在 N 原子或侧链中带有金刚烷基部分的胺和二胺的无催化剂反应。在氨基上不含仲烷基取代基的胺与过量的 2-氟吡啶反应生成 N-(吡啶-2-基)衍生物，产率从中等到高。发现 2-氟-5-卤代吡啶比 2-氟吡啶更具反应性。
• Synthesis of epoxide hydrolase sEH inhibitors and study of its inhibitory properties
  作者：G. M. Butov、V. V. Burmistrov、D. V. Danilov、A. D. Averin、C. Morisseau、S. Kodani、B. D. Hammock

  DOI：10.1007/s11172-016-1581-y

  日期：2016.9

  Adamantyl-containing 1,3-disubstituted ureas, bisureas, and biscarbamates containing different spacers between the ureylene or the carbamate groups and the adamantyl radical were synthesized. Their inhibitory activity against soluble epoxide hydrolases of mammals and humans (sEH, E.C. 3.3.2.10) was studied. The compounds were found to possess high inhibitory activity on the level of 0.8—2.7 nmol L–1. A relationship between the inhibitor structure and its activity was established.

  研究人员合成了含金刚烷基的 1,3-二取代脲基、双脲基和双氨基甲酸酯，其中脲基或氨基甲酸酯基团与金刚烷基之间有不同的间隔。研究了它们对哺乳动物和人类的可溶性环氧化物水解酶（sEH，E.C. 3.3.2.10）的抑制活性。研究发现，这些化合物具有 0.8-2.7 nmol L-1 的高抑制活性。研究还确定了抑制剂结构与其活性之间的关系。
• Mono- and Diamination of 4,6-Dichloropyrimidine, 2,6-Dichloropyrazine and 1,3-Dichloroisoquinoline with Adamantane-Containing Amines
  作者：Alisa D. Kharlamova、Anton S. Abel、Alexei D. Averin、Olga A. Maloshitskaya、Vitaly A. Roznyatovskiy、Evgenii N. Savelyev、Boris S. Orlinson、Ivan A. Novakov、Irina P. Beletskaya

  DOI：10.3390/molecules26071910

  日期：——

  N-heteroaryl substituted adamantane-containing amines are of substantial interest for their perspective antiviral and psychotherapeutic activities. Chlorine atom at alpha-position of N-heterocycles has been substituted by the amino group using convenient nucleophilic substitution reactions with a series of adamantylalkylamines. The prototropic equilibrium in these compounds was studied using NMR spectroscopy. The introduction of the second amino substituent in 4-amino-6-chloropyrimidine, 2-amino-chloropyrazine, and 1-amino-3-chloroisoquinoline was achieved using Pd(0) catalysis.

  含有N-杂环取代的金刚烷胺对其具有潜在的抗病毒和精神治疗活性而引起了极大的兴趣。通过使用一系列金刚烷烷基胺进行便利的亲核取代反应，将N-杂环的α-位置的氯原子取代为氨基。利用核磁共振光谱研究了这些化合物中的质子平衡。通过Pd(0)催化，成功在4-氨基-6-氯吡咯嘧啶，2-氨基氯吡嗪和1-氨基-3-氯异喹啉中引入了第二个氨基取代基。