2-(4-tert-butylphenyl)-6-isopropylquinoline | 195437-49-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 2-(4-tert-butylphenyl)-6-isopropylquinoline
• 英文别名: (+)-2-(4-Tert-butylphenyl)-6-isopropylquinoline；2-(4-tert-butylphenyl)-6-propan-2-ylquinoline
• CAS: 195437-49-1
• 化学式: C₂₂H₂₅N
• 分子量: 303.447
• InChiKey: LGDXDPNAHZJWBK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-(4-tert-butylphenyl)-6-isopropylquinoline 在 氢气 作用下， 以 水 、 异丙醇 为溶剂， 以93%的产率得到2-(4-(tert-butyl)phenyl)-6-isopropyl-1,2,3,4-tetrahydroquinoline
  参考文献：
  名称：

  用于取代（异）喹诺酮选择性加氢的强大铁催化剂†

  摘要：

  通过应用氮掺杂碳改性铁基催化剂，实现了N-杂芳烃，特别是（异）喹诺酮类化合物的受控加氢。活性的关键是通过热解碳浸渍复合材料制备催化剂，该复合材料由乙酸铁( II )和N-芳基亚氨基吡啶获得。 TEM、XRD、XPS 和拉曼光谱表明，合成的材料由 N 掺杂碳基体中的 Fe(0)、Fe 3 C 和 FeN x组成。这种坚固且易于回收的铁材料具有良好的催化活性，即使在存在可还原官能团（例如腈、卤素、酯和酰胺）的情况下，也可以选择性氢化各种（异）喹啉衍生物。为了进行概念验证，这种纳米结构催化剂被应用于天然产物和药物先导化合物的多步合成以及光致发光材料的改性中。因此，该方法构成了具有合成重要性的取代（异）喹诺酮的第一个非均相铁催化氢化。

  DOI：

  10.1039/c8sc02744g
• 作为产物：
  描述：

  6-异丙基喹啉 、 4-叔丁基苯基溴化镁 以 四氢呋喃 、 乙醚 为溶剂， 以40%的产率得到2-(4-tert-butylphenyl)-6-isopropylquinoline
  参考文献：
  名称：

  Design, Synthesis, and Pharmacological Evaluation of Conformationally Constrained Analogues of N,N‘-Diaryl- and N-Aryl-N-aralkylguanidines as Potent Inhibitors of Neuronal Na⁺ Channels

  摘要：

  In the present investigation, the rationale for the design, synthesis, and biological evaluation of potent inhibitors of neuronal Nai channels is described. N,N'-Diaryl- and N-aryl-N-aralkylguanidine templates were locked in conformations mimicking the permissible conformations of the flexible diarylguanidinium ion (AS(+), AA(+), SS+). The resulting set of constrained guanidines termed "lockamers" (cyclophane, quinazoline, aminopyrimidazolines, aminoimidazolines azocino- and tetrahydroquinolinocarboximidamides) was examined for neuronal Na+ channel blockade properties. Inhibition of [C-14]guanidinium ion influx in CHO cells expressing type IIA Na+ channels showed that the aminopyrimidazoline 9b and aminoimidazoline 9d, compounds proposed to lock the N,N'-diarylguanidinium in an SS+ conformation, were the most potent Na+ channel blockers with IC50's of 0.06 mu M, a value 17 times lower than that of the parent flexible compound 18d. The rest of the restricted analogues with 4-p-alkyl substituents retained potency with IC50 values ranging between 0.46 and 2.9 mu M. Evaluation in a synaptosomal Ca-45(2+) influx assay showed that 9b did not exhibit high selectivity for neuronal Na+ vs Ca2+ channels. The retention of significant neuronal Na+ blockade in all types of semirigid conformers gives evidence for a multiple mode of binding in this class of compounds and can possibly be attributed to a poor structural specificity of the site(s) of action. Compound 9b was also found to be the most active compound in vivo based on the high level of inhibition of seizures exhibited in the DBA/2 mouse model. The pK(a) value of 9b indicates that 9b binds to the channel in its protonated form, and log D vs pH measurements suggest that ion-pair partitioning contributes to membrane transport. This compound stands out as an interesting lead for further development of neurotherapeutic agents.

  DOI：

  10.1021/jm980124a

文献信息

• Pharmaceutically active compounds and methods of use
  申请人：——

  公开号：US20020099084A1

  公开（公告）日：2002-07-25

  The present invention relates to pharmaceutically acceptable compounds, including certain substituted indolinyl and derivatives thereof, 1,2,3,4-tetrahydroquinolinyl and derivatives thereof, 1,2,3,4-tetrahydroisoquinolinyl, benz[cd]indolinyl and 5,6-dihydrophenanthridinyl compounds, and methods of treatment and pharmaceutical compositions that utilize or comprise one or more such compounds. Compounds of the invention are particularly useful for the treatment or prophylaxis of neurological injury and neurodegenerative disorders.

  本发明涉及药学上可接受的化合物，包括某些取代的吲哚啉及其衍生物、1,2,3,4-四氢喹啉及其衍生物、1,2,3,4-四氢异喹啉、苯并[cd]吲哚啉和5,6-二氢苯并喹啉化合物，以及利用或包含一种或多种这样的化合物的治疗方法和制药组合物。本发明的化合物特别适用于神经损伤和神经退行性疾病的治疗或预防。
• Pharmaceutically active nitrogen ring compounds and methods of use thereof
  申请人：CeNes Pharmaceuticals, Inc.

  公开号：US06358993B1

  公开（公告）日：2002-03-19

  The present invention relates to pharmaceutically acceptable compounds, including certain substituted indolinyl and derivatives thereof, 1,2,3,4-tetrahydroquinolinyl and derivatives thereof, 1,2,3,4-tetrahydroisoquinolinyl, benz[cd]indolinyl and 5,6-dihydrophenanthridinyl compounds, and methods of treatment and pharmaceutical compositions that utilize or comprise one or more such compounds. Compounds of the invention are particularly useful for the treatment or prophylaxis of neurological injury and neurodegenerative disorders.

  本发明涉及药学上可接受的化合物，包括某些取代的吲哚啉及其衍生物、1,2,3,4-四氢喹啉及其衍生物、1,2,3,4-四氢异喹啉、苯并[cd]吲哚啉和5,6-二氢苯并喹啉化合物，以及利用或包含一个或多个这样的化合物的治疗方法和制药组合物。本发明的化合物特别适用于治疗或预防神经损伤和神经退行性疾病。
• US6025355
  申请人：——

  公开号：——

  公开（公告）日：——
• PHARMACEUTICALLY ACTIVE COMPOUNDS AND METHODS OF USE
  申请人：CAMBRIDGE NEUROSCIENCE, INC.

  公开号：EP0925300A1

  公开（公告）日：1999-06-30
• EP0925300A4
  申请人：——

  公开号：EP0925300A4

  公开（公告）日：1999-06-30