N-acetyl-3-n-propyl-1-aminoadamantane | 80121-63-7

• 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
• 英文名称: N-acetyl-3-n-propyl-1-aminoadamantane
• 英文别名: 1-acetamido-3-propyladamantane；N-(3-propyl-1-adamantyl)acetamide
• CAS: 80121-63-7
• 化学式: C₁₅H₂₅NO
• 分子量: 235.37
• InChiKey: UENKJQSIOSMAIE-UHFFFAOYSA-N

物化性质

• 熔点：
  104-104.5 °C
• 沸点：
  377.2±9.0 °C(predicted)
• 密度：
  1.03±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.93
• 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-acetyl-3-n-propyl-1-aminoadamantane 在 4-二甲氨基吡啶 、 硫酸 、 硝酸 、 三乙胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 二乙二醇 为溶剂， 反应 53.0h， 生成
  参考文献：
  名称：

  Synthesis and biological evaluation of memantine nitrates as a potential treatment for neurodegenerative diseases

  摘要：

  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。

  DOI：

  10.1039/c6md00509h
• 作为产物：
  描述：

  1-Propyladamantane 在 溴 作用下， 反应 4.0h， 生成 N-acetyl-3-n-propyl-1-aminoadamantane
  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

• HENKEL, J. G.;HANE, J. T.;GIANUTSOS, G., J. MED. CHEM., 1982, 25, N 1, 51-56
  作者：HENKEL, J. G.、HANE, J. T.、GIANUTSOS, G.

  DOI：——

  日期：——
• Method for Inhibition of Potential-Dependent Cation Channel
  申请人：Takatoku Hiroko

  公开号：US20130045177A1

  公开（公告）日：2013-02-21

  An excellent potential-dependent cation channel inhibitor or an excellent masking agent is provided. Disclosed is a method for inhibiting a potential-dependent cation channel or a method for masking olfaction, both of which include administering an adamantane derivate represented by the following formula (1) or a salt thereof [wherein R′ and R 2 are identical with or different from each other, and each represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms; and X represents —OH, —R 3 —OH (wherein R 3 represents an alkylene group having 1 to 6 carbon atoms), —NH 2 , —R 4 —NH 2 (wherein R 4 represents an alkylene group having 1 to 6 carbon atoms), —COOH, —R 5 —COOH (wherein R 5 represents an alkylene group having 1 to 6 carbon atoms), —CO-R 6 (wherein R 6 represents an alkyl group having 1 to 6 carbon atoms), —CO—R 7 —COO—R 8 (wherein R 7 represents an alkylene group having 1 to 6 carbon atoms, and R 8 represents an alkyl group having 1 to 6 carbon atoms), or —NHCO—R 9 (wherein R 9 represents an alkyl group having 1 to 6 carbon atoms)].
• US8481016B2
  申请人：——

  公开号：US8481016B2

  公开（公告）日：2013-07-09
• 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。
• Structure-anti-Parkinson activity relationships in the aminoadamantanes. Influence of bridgehead substitution
  作者：James G. Henkel、Jeffrey T. Hane、Gerald Gianutsos

  DOI：10.1021/jm00343a010

  日期：1982.1

  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.