1-金刚烷基-(2-氰基乙基)铵 | 32901-14-7

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: 1-金刚烷基-(2-氰基乙基)铵
• 英文名称: 3-(1-adamantylamino)propionitrile
• 英文别名: 3-(Adamantan-1-ylamino)-propionitrile；3-(1-adamantylamino)propanenitrile
• CAS: 32901-14-7
• 化学式: C₁₃H₂₀N₂
• mdl: MFCD03964659
• 分子量: 204.315
• InChiKey: DRROTNRHCXFLBA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.923
• 拓扑面积：
  35.8
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2926909090

反应信息

• 作为反应物：
  描述：

  1-金刚烷基-(2-氰基乙基)铵 在 lithium aluminium tetrahydride 、 N,N'-羰基二咪唑 作用下， 以 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 26.0h， 生成 N-[3-(1-adamantylamino)propyl]-1H-indazole-3-carboxamide
  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
• 作为产物：
  描述：

  金刚烷胺 、 丙烯腈 生成 1-金刚烷基-(2-氰基乙基)铵
  参考文献：
  名称：

  新型咪唑4-羧酸衍生物的合成及抗血小板活性

  摘要：

  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)

  DOI：

  10.1002/ardp.200500150

文献信息

• Adamantyl aziridines via aza-Michael initiated ring closure (aza-MIRC) reaction
  作者：Alena I. Fedotova、Tatiana A. Komarova、Alexey R. Romanov、Igor A. Ushakov、Julien Legros、Jacques Maddaluno、Alexander Yu. Rulev

  DOI：10.1016/j.tet.2017.01.006

  日期：2017.2

  An efficient one-pot synthesis of functionalized adamantylaziridines by aza-Michael initiated ring closure (aza-MIRC) reaction of 1-aminoadamantane with α-halogenated Michael acceptors is described. The reaction goes through an aza-Michael intermediate that undergoes an intramolecular nucleophilic substitution. Expectedly, high pressure exerts a beneficial influence in the case of sterically hindered

  描述了通过1-氨基金刚烷与α-卤代迈克尔受体的氮杂-迈克尔引发的闭环（aza-MIRC）反应的有效的一锅合成功能化的金刚烷基氮丙啶。该反应通过氮杂-迈克尔中间体，该中间体经历分子内亲核取代。预期地，在空间受阻试剂的情况下，高压会产生有益的影响。
• Generation and <i>in Situ</i> Evaluation of Libraries of Poly(acrylic acid) Presenting Sialosides as Side Chains as Polyvalent Inhibitors of Influenza-Mediated Hemagglutination
  作者：Seok-Ki Choi、Mathai Mammen、George M. Whitesides

  DOI：10.1021/ja963519x

  日期：1997.5.1

  This paper describes a simple, microscale method for generating and evaluating libraries of derivatives of poly(acrylic acid) (pAA) that present mixtures of side chains that influence their biological activity. The method is based on the one-step conversion of poly(acrylic anhydride) (pAAn) to linear polymers presenting multiple units of R on side chains, pAA(R): the polymers are obtained by ultrasonication of a suspension of pAAn and aqueous RNH2 contained in a 250-mu L well of a microtiter plate. Using this method, derivatives of pAA having N-acetylneuraminic acid (NeuAc-L-NH2) as a side chain, pAA(NeuAc-L), were generated and assayed for ability to inhibit hemagglutination (HAI) of chicken erythrocytes by influenza virus A (X-31); the constant (KHAT) describing this inhibition is calculated on the basis of the concentration of NeuAc groups in solution, rather than the concentration of polymer molecules. Go-polymeric pAA(NeuAc-L-n; L-n=different linking groups) with a range of mole fractions of NeuAc-L-NH2 (chi(NeuAc-L)=0.02-0.11) exhibited HAI activities with K-i(HAI) values between 27 and 0.30 mu M. Using combinations of NeuAc-L-NH2 and one of 26 different primary amines RNH2, a variety of ter-polymeric pAA(NeuAc-L; R) (chi(Neu-Ac-L)similar to 0.05; chi(R) similar to 0.06) were also generated and assayed. Certain ter-polymers yielded values of K-i(HAI) that were lower by a factor of similar to 10(4) than that of the parent co-polymeric pAA(NeuAc-L): the most active inhibitor was pAA(NeuAc-L; L-3-(2'-naphthyl)alanine)) (K(i)(HAI)approximate to 0.05 mM). Typically, the incorporation of hydrophobic-especially aromatic-side chains enhanced activities. These polymers (pAA(NeuAc-L; R)) belong to a new class of polymeric, polyvalent sialosides that are potent inhibitors of the adsorption of influenza virus to erythrocytes. They were active with only low to moderate levels of incorporation of functional groups into the side chains: chi(NeuAc-L)similar to 0.05; chi(R) similar to 0.06.
• PLAXOTNIK, V. M.;KOVTUN, V. YU.;YASHUNSKIJ, V. G.;GALEGOV, G. A.;PETROVA,+
  作者：PLAXOTNIK, V. M.、KOVTUN, V. YU.、YASHUNSKIJ, V. G.、GALEGOV, G. A.、PETROVA,+

  DOI：——

  日期：——
• PLAXOTNIK, V. M.;KOVTUN, V. YU.;LEONTEVA, N. A.;PETROVA, I. G.;PUSHKARSKA+, XIM.-FARMATS. ZH., 1982, 16, N 7, 810-814
  作者：PLAXOTNIK, V. M.、KOVTUN, V. YU.、LEONTEVA, N. A.、PETROVA, I. G.、PUSHKARSKA+

  DOI：——

  日期：——
• Synthesis and antiviral activity of N-substituted aminoadamantanes
  作者：V. M. Plakhotnik、V. Yu. Kovtun、N. A. Leont'eva、I. G. Petrova、N. L. Pushkarskaya、G. A. Galegov

  DOI：10.1007/bf00761547

  日期：1982.7