N-乙酰基去甲基美金刚 | 778-09-6

• 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: N-乙酰基去甲基美金刚
• 英文名称: 1-Acetamino-3-methyl-adamantan
• 英文别名: N-(3-methyl-1-adamantyl)acetamide
• CAS: 778-09-6
• 化学式: C₁₃H₂₁NO
• 分子量: 207.316
• InChiKey: SANVSQCVSVDXSG-UHFFFAOYSA-N

物化性质

• 熔点：
  111-113°C
• 沸点：
  349.9±9.0 °C(Predicted)
• 密度：
  1.06±0.1 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿（少许）、DMSO（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-乙酰基去甲基美金刚 在 sodium hydroxide 作用下， 以 二乙二醇 为溶剂， 生成 3-甲基金刚烷-1-胺
  参考文献：
  名称：

  Structure-anti-Parkinson activity relationships in the aminoadamantanes. Influence of bridgehead substitution

  摘要：

  A limited series of bridgehead alkyl-, dialkyl-, and trialkyl-substituted amantadines was synthesized and tested for potential anti-Parkinson activity as dopamine (DA) agonists. The compounds were evaluated using a battery of three murine bioassays, including stimulation of locomotor activity, induction of circling in animals with unilateral striatal lesions, and reversal of reserpine/alpha-methyltyrosine induced akinesia. Apparent mechanistic differences were seen between the methyl-substituted series and the ethyl-substituted series. While activities in both series increase with increasing liphophilicity, the methyl series (1b--d), as well as amantadine itself (1a), exhibit only indirect DA agonist activity, as evidenced by ipsilateral rotation in the circling model and no significant difference from control in reversal of akinesia. The ethyl series (1e,f) exhibits weak but reproducible direct DA agonist activity, as shown by contralateral rotation in the circling assay for 1e and reversal of akinesia by 1e and 1f. The 3-n-propyl derivative (1g) was devoid of any DA agonist activity.

  DOI：

  10.1021/jm00343a010
• 作为产物：
  描述：

  3-甲基-1-金刚烷醇 在 溴 、 三苯基膦 作用下， 以 乙腈 为溶剂， 反应 30.0h， 生成 N-乙酰基去甲基美金刚
  参考文献：
  名称：

  Structure-anti-Parkinson activity relationships in the aminoadamantanes. Influence of bridgehead substitution

  摘要：

  A limited series of bridgehead alkyl-, dialkyl-, and trialkyl-substituted amantadines was synthesized and tested for potential anti-Parkinson activity as dopamine (DA) agonists. The compounds were evaluated using a battery of three murine bioassays, including stimulation of locomotor activity, induction of circling in animals with unilateral striatal lesions, and reversal of reserpine/alpha-methyltyrosine induced akinesia. Apparent mechanistic differences were seen between the methyl-substituted series and the ethyl-substituted series. While activities in both series increase with increasing liphophilicity, the methyl series (1b--d), as well as amantadine itself (1a), exhibit only indirect DA agonist activity, as evidenced by ipsilateral rotation in the circling model and no significant difference from control in reversal of akinesia. The ethyl series (1e,f) exhibits weak but reproducible direct DA agonist activity, as shown by contralateral rotation in the circling assay for 1e and reversal of akinesia by 1e and 1f. The 3-n-propyl derivative (1g) was devoid of any DA agonist activity.

  DOI：

  10.1021/jm00343a010

文献信息

• γ-Aminoadamantanecarboxylic Acids Through Direct C–H Bond Amidations
  作者：Lukas Wanka、Chiara Cabrele、Maksims Vanejews、Peter R. Schreiner

  DOI：10.1002/ejoc.200600975

  日期：2007.3

  bromine-free, direct C–H bond amidations we have synthesized a large variety of adamantane amides. Depending on the precursors used these amides directly yield pharmaceutically active aminoadamantanes or γ-aminoadamantanecarboxylic acids after hydrolytic cleavage. Theserigid analogues of γ-aminobutyric acid (GABA) were protected at the C- and N-termini and we synthesized a number of peptides incorporating γ-a

  利用不含溴的直接 C-H 键酰胺化，我们合成了多种金刚烷酰胺。根据所使用的前体，这些酰胺在水解裂解后直接产生具有药学活性的氨基金刚烷或 γ-氨基金刚烷羧酸。这些 γ-氨基丁酸 (GABA) 的刚性类似物在 C 端和 N 端受到保护，我们合成了许多在溶液中结合 γ-氨基金刚烷羧酸的肽，以及通过固相肽合成。这些肽是用于药物化学和有机催化应用的有前途的支架。 (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)
• Synthesis and biological evaluation of memantine nitrates as a potential treatment for neurodegenerative diseases
  作者：Zheng Liu、Si Yang、Xiaoyong Jin、Gaoxiao Zhang、Baojian Guo、Haiyun Chen、Pei Yu、Yewei Sun、Zaijun Zhang、Yuqiang Wang

  DOI：10.1039/c6md00509h

  日期：——

  A series of memantine nitrate derivatives, as dual functional compounds with neuroprotective and vasodilatory activity for neurodegenerative diseases, was designed and synthesized.

  一系列甲基苯胺硝酸盐衍生物被设计和合成，作为具有神经保护和血管舒张活性的双重功能化合物，用于神经退行性疾病。
• WO2007/126886
  申请人：——

  公开号：——

  公开（公告）日：——
• Stetter,H.; Gaertner,J., Chemische Berichte, 1966, vol. 99, p. 925 - 929
  作者：Stetter,H.、Gaertner,J.

  DOI：——

  日期：——
• Anodic chemistry of adamantyl compounds. Scissible carbon, halogen, hydrogen, and oxygen substituents
  作者：Victor R. Koch、Larry L. Miller

  DOI：10.1021/ja00807a022

  日期：1973.12