2-氨基金刚烷基-2-羧酸甲酯 | 144876-68-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: 2-氨基金刚烷基-2-羧酸甲酯
• 英文名称: 2-aminoadamantyl-2-carboxylic acid methyl ester
• 英文别名: Methyl 2-aminoadamantane-2-carboxylate
• CAS: 144876-68-6
• 化学式: C₁₂H₁₉NO₂
• 分子量: 209.288
• InChiKey: PYOLCEFLWZRKCO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  52.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-氨基金刚烷基-2-羧酸甲酯 在 三乙胺 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 20.0h， 生成 phenylmethyl-4-(1H-indol-3-ylmethyl)-1-<2-(methoxycarbonyl)tricyclo<3.3.1.1^3,7>-dec-2-yl>-4-methyl-2,5-dioxo-8-phenyl-1,3,6,9-tetraazadecan-10-oate
  参考文献：
  名称：

  Synthesis and CCK-B binding affinities of cyclic analogues of the potent and selective CCK-B receptor antagonist Cl-988

  摘要：

  A selected series of 14-membered macrocyclic compounds (2) has been prepared as potential CCK-B receptor selective ligands. The efficiency of a number of cyclising reagents has also been evaluated.

  DOI：

  10.1016/s0040-4020(01)86596-0
• 作为产物：
  描述：

  2-氨基金刚烷-2-甲酸 在 palladium hydroxide - carbon sodium hydroxide 、 氢气 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醚 、 水 、 异丙醇 为溶剂， 25.0~60.0 ℃ 、413.69 kPa 条件下， 反应 25.0h， 生成 2-氨基金刚烷基-2-羧酸甲酯
  参考文献：
  名称：

  Synthesis and CCK-B binding affinities of cyclic analogues of the potent and selective CCK-B receptor antagonist Cl-988

  摘要：

  A selected series of 14-membered macrocyclic compounds (2) has been prepared as potential CCK-B receptor selective ligands. The efficiency of a number of cyclising reagents has also been evaluated.

  DOI：

  10.1016/s0040-4020(01)86596-0

文献信息

• Leucettinibs, a Class of DYRK/CLK Kinase Inhibitors Inspired by the Marine Sponge Natural Product Leucettamine B
  作者：Emmanuel Deau、Mattias F. Lindberg、Frédéric Miege、Didier Roche、Nicolas George、Pascal George、Andreas Krämer、Stefan Knapp、Laurent Meijer

  DOI：10.1021/acs.jmedchem.3c00884

  日期：2023.8.10

  cdc2-like kinases (CLKs) recently attracted attention due to their central involvement in various pathologies. We here describe a family of DYRK/CLK inhibitors derived from Leucettines and the marine natural product Leucettamine B. Forty-five N2-functionalized 2-aminoimidazolin-4-ones bearing a fused [6 + 5]-heteroarylmethylene were synthesized. Benzothiazol-6-ylmethylene was selected as the most potent residue

  双特异性酪氨酸磷酸化调节激酶 (DYRK) 和 cdc2 样激酶 (CLK) 最近因其在各种病理学中的重要参与而引起了人们的关注。我们在此描述了一系列源自亮氨酰胺和海洋天然产物亮氨酰胺 B 的 DYRK/CLK 抑制剂。合成了 45 种带有融合的 [6 + 5]-杂芳基亚甲基的N 2-官能化 2-氨基咪唑啉-4-酮。苯并噻唑-6-基亚甲基被选为 15 个不同杂芳基亚甲基中最有效的残基。合成并广泛表征了186 个带有苯并噻唑-6-基亚甲基的N 2-取代 2-氨基咪唑啉-4-酮，统称为 Leucettinib。鉴定出亚纳摩尔 IC 50 （DYRK1A 为 0.5-20 nM）抑制剂，并在 DYRK1A 中对一种 Leucettinib 进行建模，并与 CLK1 和较弱抑制的脱靶 CSNK2A1 共结晶。合成了 Leucettinib 的激酶失活异构体（DYRK1A 上 >3–10 μM），称为
• N-Methylation of adamantane-substituted oxalamide unit affects its conformational rigidity: A skew conformation of the oxalamide bridge
  作者：Zoran Džolić、Renato Margeta、Marijana Vinković、Zoran Štefanić、Biserka Kojić-Prodić、Kata Mlinarić-Majerski、Mladen Žinić

  DOI：10.1016/j.molstruc.2007.06.024

  日期：2008.3

  The synthesis of adamantane functionalized retropeptides, N,N'-bis(2-adamantyl-2-carboxylic acid methyl ester)oxalamide (1) and Nmethyl-N,N'-bis(2-adamantyl-2-carboxylic acid methyl ester)oxalamide (2), as well as the influence of the N-methylation on the conformational preferences of oxalamide group are described. In the solid state the oxalamide group of I is planar while in the retropeptide 2 adopts a skew-conformation. (c) 2007 Elsevier B.V. All rights reserved.
• Synthesis and CCK-B binding affinities of cyclic analogues of the potent and selective CCK-B receptor antagonist Cl-988
  作者：Eric Didier、David C. Horwell、Martyn C. Pritchard

  DOI：10.1016/s0040-4020(01)86596-0

  日期：1992.9

  A selected series of 14-membered macrocyclic compounds (2) has been prepared as potential CCK-B receptor selective ligands. The efficiency of a number of cyclising reagents has also been evaluated.