2-isobutyl-1H-imidazole-5-carbaldehyde | 1343019-46-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-isobutyl-1H-imidazole-5-carbaldehyde
• 英文别名: 2-(2-methylpropyl)-1H-imidazole-5-carbaldehyde
• CAS: 1343019-46-4
• 化学式: C₈H₁₂N₂O
• 分子量: 152.196
• InChiKey: GLFULFPNENOSTK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  45.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1R,2R,3R,5S)-(-)-Isopinocampheylamine 、 2-isobutyl-1H-imidazole-5-carbaldehyde 在 三乙酰氧基硼氢化钠 、 盐酸 作用下， 以 1,2-二氯乙烷 、 乙酸乙酯 为溶剂， 反应 1.5h， 以63.5%的产率得到(1R,2R,3R,5S)-N-((2-isobutyl-1H-imidazol-5-yl)methyl)-2,6,6-trimethylbicyclo[3.1.1]heptan-3-amine hydrochloride
  参考文献：
  名称：

  Imidazole-based pinanamine derivatives: Discovery of dual inhibitors of the wild-type and drug-resistant mutant of the influenza A virus

  摘要：

  We previously reported potent hit compound 4 inhibiting the wild-type influenza A virus A/HK/68 (H3N2) and A/M2-S31N mutant viruses A/WS/33 (H1N1), with its latter activity quite weak. To further increase its potency, a structure-activity relationship study of a series of imidazole-linked pinanamine derivatives was conducted by modifying the imidazole ring of this compound. Several compounds of this series inhibited the amantadine-sensitive virus at low micromolar concentrations. Among them, 33 was the most potent compound, which was identified as being active on an amantadine-sensitive virus through blocking of the viral M2 ion channel. Furthermore, 33 markedly inhibited the amantadine-resistant virus (IC50 = 3.4 mu M) and its activity increased by almost 24-fold compared to initial compound, with its action mechanism being not M2 channel mediated. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.12.013
• 作为产物：
  描述：

  2-异丁基-1H-咪唑 在 正丁基锂 、 sodium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.5h， 生成 2-isobutyl-1H-imidazole-5-carbaldehyde
  参考文献：
  名称：

  Imidazole-based pinanamine derivatives: Discovery of dual inhibitors of the wild-type and drug-resistant mutant of the influenza A virus

  摘要：

  We previously reported potent hit compound 4 inhibiting the wild-type influenza A virus A/HK/68 (H3N2) and A/M2-S31N mutant viruses A/WS/33 (H1N1), with its latter activity quite weak. To further increase its potency, a structure-activity relationship study of a series of imidazole-linked pinanamine derivatives was conducted by modifying the imidazole ring of this compound. Several compounds of this series inhibited the amantadine-sensitive virus at low micromolar concentrations. Among them, 33 was the most potent compound, which was identified as being active on an amantadine-sensitive virus through blocking of the viral M2 ion channel. Furthermore, 33 markedly inhibited the amantadine-resistant virus (IC50 = 3.4 mu M) and its activity increased by almost 24-fold compared to initial compound, with its action mechanism being not M2 channel mediated. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.12.013

文献信息

• LRRK2 INHIBITORS
  申请人：Bounaud Pierre-Yves

  公开号：US20140205537A1

  公开（公告）日：2014-07-24

  Provided herein are compounds that inhibit or partially inhibit the activity of leucine rich repeat kinases. Also provided herein are methods of treatment of CNS disorders comprising administration of inhibitors of leucine rich repeat kinases.

  本文提供了抑制或部分抑制富含亮氨酸重复激酶活性的化合物。本文还提供了治疗中枢神经系统疾病的方法，包括给予富含亮氨酸重复激酶抑制剂的治疗。
• Highly Efficient, Environment-Friendly, One-Pot Synthesis of 2-Substituted 4-Formylimidazoles from 4-Acylaminoisoxazoles
  作者：Feng Gao、Xin-Chuan Tian、Xiao-Xia Qu、Dan Wang、Dong Pu

  DOI：10.1055/s-0034-1379201

  日期：——

  A highly efficient and environment-friendly one-pot synthesis of 2-substituted 4-formylimidazoles was accomplished. Raney nickel catalyzed hydrogenation of 4-acylaminoisoxazoles in ethanol, followed by sodium hydroxide promoted recyclization of the ring-opened intermediates, afforded the functionalized imidazoles.
• [EN] LRRK2 INHIBITORS<br/>[FR] INHIBITEURS DE LRRK2
  申请人：ZENOBIA THERAPEUTICS INC

  公开号：WO2012178015A2

  公开（公告）日：2012-12-27

  Provided herein are compounds that inhibit or partially inhibit the activity of leucine rich repeat kinases. Also provided herein are methods of treatment of CNS disorders comprising administration of inhibitors of leucine rich repeat kinases.
• [EN] IMIDAZOLE COMPOUND AND MEDICINE COMPRISING SAME<br/>[FR] COMPOSÉ IMIDAZOLE ET MÉDICAMENT COMPRENANT CELUI-CI<br/>[JA] イミダゾール化合物及びこれを含有する医薬
  申请人：JAPAN SCIENCE & TECH AGENCY

  公开号：WO2017164173A1

  公开（公告）日：2017-09-28

  優れたＡβ凝集阻害作用を有し、医薬として有用な新たな化合物の提供。　次の一般式（１）（式中、Ａ、Ｂ及びＣは、同一又は異なって、窒素原子又は炭素原子を示し；　Ｘ1及びＸ2は、同一又は異なって、－ＣＨ2－、－Ｏ－又は－Ｓ－を示し；　Ｒ1及びＲ2は、同一又は異なって、置換基を有していてもよい芳香族炭化水素基等を示し；　Ｒ3は、水素原子、又は直鎖若しくは分岐鎖アルキル基を示し；　Ｒ4は、直鎖若しくは分岐鎖アルキル基、又は環状アルキル基を示し；　Ｒ3とＲ4は隣接する窒素原子と一緒になって飽和複素環を形成してもよく；　Ｒ5は、直鎖若しくは分岐鎖アルキル基、又は環状アルキル基を示し；　Ｒ6及びＲ7は、いずれか一方が、水素原子又はアルキル基を示し；　イミダゾール環内の破線は、二重結合が一個存在することを示す。） で表されるイミダゾール化合物又はその塩。
• Imidazole-based pinanamine derivatives: Discovery of dual inhibitors of the wild-type and drug-resistant mutant of the influenza A virus
  作者：Jianghong Dong、Shengwei Chen、Runfeng Li、Wei Cui、Haiming Jiang、Yixia Ling、Zifeng Yang、Wenhui Hu

  DOI：10.1016/j.ejmech.2015.12.013

  日期：2016.1

  We previously reported potent hit compound 4 inhibiting the wild-type influenza A virus A/HK/68 (H3N2) and A/M2-S31N mutant viruses A/WS/33 (H1N1), with its latter activity quite weak. To further increase its potency, a structure-activity relationship study of a series of imidazole-linked pinanamine derivatives was conducted by modifying the imidazole ring of this compound. Several compounds of this series inhibited the amantadine-sensitive virus at low micromolar concentrations. Among them, 33 was the most potent compound, which was identified as being active on an amantadine-sensitive virus through blocking of the viral M2 ion channel. Furthermore, 33 markedly inhibited the amantadine-resistant virus (IC50 = 3.4 mu M) and its activity increased by almost 24-fold compared to initial compound, with its action mechanism being not M2 channel mediated. (C) 2015 Elsevier Masson SAS. All rights reserved.