3,5-diethyl-1-bromoadamantane | 25074-52-6

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 有机溴化物
• 英文名称: 3,5-diethyl-1-bromoadamantane
• 英文别名: 1-Bromo-3,5-diethyladamantane
• CAS: 25074-52-6
• 化学式: C₁₄H₂₃Br
• 分子量: 271.241
• InChiKey: JJJHMTZMITZWDM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  3,5-diethyl-1-bromoadamantane 在 lithium aluminium tetrahydride 、 氯化亚砜 、 硫酸 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 9.0h， 生成
  参考文献：
  名称：

  一种新的金刚乙胺类似物及其合成方法

  摘要：

  本发明提供了本发明提供了一种新的金刚乙胺类似物，其结构如式(Ⅰ)所示：本发明所述揭示的金刚乙胺类似物，其活性更好，更有利于药物的临床使用和进一步开发研究。

  公开号：

  CN109574856A
• 作为产物：
  描述：

  1,3-金刚烷二乙酸 在 吡啶 、 lithium aluminium tetrahydride 、 溴 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 21.0h， 生成 3,5-diethyl-1-bromoadamantane
  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

• Stepanov,F.N. et al., Journal of Organic Chemistry USSR (English Translation), 1969, vol. 5, p. 2123 - 2125
  作者：Stepanov,F.N. et al.

  DOI：——

  日期：——
• 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：——
• US4122193A
  申请人：——

  公开号：US4122193A

  公开（公告）日：1978-10-24
• 一种新的金刚乙胺类似物及其合成方法
  申请人：无锡福祈制药有限公司

  公开号：CN109574856A

  公开（公告）日：2019-04-05

  本发明提供了本发明提供了一种新的金刚乙胺类似物，其结构如式(Ⅰ)所示：本发明所述揭示的金刚乙胺类似物，其活性更好，更有利于药物的临床使用和进一步开发研究。
• 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.