2-methyl-4-(prop-2-enyl)quinoline | 38178-77-7

• 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-methyl-4-(prop-2-enyl)quinoline
• 英文别名: 4-allyl-2-methylquinoline；4-Allyl-2-methyl-chinolin；4-Allyl-2-methylchinolin；2-Methyl-4-prop-2-enylquinoline
• CAS: 38178-77-7
• 化学式: C₁₃H₁₃N
• 分子量: 183.253
• InChiKey: ITOYOHUQSQWBEO-UHFFFAOYSA-N

物化性质

• 沸点：
  295.5±9.0 °C(Predicted)
• 密度：
  1.032±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 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-methyl-4-(prop-2-enyl)quinoline 在 咪唑 、 selenium(IV) oxide 、 硼烷四氢呋喃络合物 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成
  参考文献：
  名称：

  Synthesis of Fluorine-Containing Phosphodiesterase 10A (PDE10A) Inhibitors and the In Vivo Evaluation of F-18 Labeled PDE10A PET Tracers in Rodent and Nonhuman Primate

  摘要：

  A series of fluorine-containing PDE10A inhibitors were designed and synthesized to improve the metabolic stability of [C-11]MP-10. Twenty of the 22 new analogues had high potency and selectivity for PDE10A: 18a-j, 19d-j, 20a-b, and 21b had IC50 values <5 nM for PDE10A. Seven F-18 labeled compounds [F-18](18)a-e, [F-18]18g, and [F-18]20a were radiosynthesized by F-18-introduction onto the quinoline rather than the pyrazole moiety of the MP-10 pharmacophore and performed in vivo evaluation. Biodistribution studies in rats showed similar to 2-fold higher activity in the PDE10A-enriched striatum than nontarget brain regions; this ratio increased from 5 to 30 min postinjection, particularly for [F-18]18a-d and [F-18]20a. Micro-PET studies of [F-18]18d and [F-18]20a in nonhuman primates provided clear visualization of striatum with suitable equilibrium kinetics and favorable metabolic stability. These results suggest this strategy may identify a F-18-labeled PET tracer for quantifying the levels of PDE10A in patients with CNS disorders including Huntington's disease and schizophrenia.

  DOI：

  10.1021/acs.jmedchem.5b01205
• 作为产物：
  描述：

  4-羟基-2-甲基喹啉 在 四(三苯基膦)钯 、 N,N-二异丙基乙胺 、 lithium bromide 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.67h， 生成 2-methyl-4-(prop-2-enyl)quinoline
  参考文献：
  名称：

  Synthesis of Fluorine-Containing Phosphodiesterase 10A (PDE10A) Inhibitors and the In Vivo Evaluation of F-18 Labeled PDE10A PET Tracers in Rodent and Nonhuman Primate

  摘要：

  A series of fluorine-containing PDE10A inhibitors were designed and synthesized to improve the metabolic stability of [C-11]MP-10. Twenty of the 22 new analogues had high potency and selectivity for PDE10A: 18a-j, 19d-j, 20a-b, and 21b had IC50 values <5 nM for PDE10A. Seven F-18 labeled compounds [F-18](18)a-e, [F-18]18g, and [F-18]20a were radiosynthesized by F-18-introduction onto the quinoline rather than the pyrazole moiety of the MP-10 pharmacophore and performed in vivo evaluation. Biodistribution studies in rats showed similar to 2-fold higher activity in the PDE10A-enriched striatum than nontarget brain regions; this ratio increased from 5 to 30 min postinjection, particularly for [F-18]18a-d and [F-18]20a. Micro-PET studies of [F-18]18d and [F-18]20a in nonhuman primates provided clear visualization of striatum with suitable equilibrium kinetics and favorable metabolic stability. These results suggest this strategy may identify a F-18-labeled PET tracer for quantifying the levels of PDE10A in patients with CNS disorders including Huntington's disease and schizophrenia.

  DOI：

  10.1021/acs.jmedchem.5b01205

文献信息

• Cobalt-Catalyzed Direct Electrochemical Cross-Coupling between Aryl or Heteroaryl Halides and Allylic Acetates or Carbonates
  作者：Paulo Gomes、Corinne Gosmini、Jacques Périchon

  DOI：10.1021/jo026421b

  日期：2003.2.1

  The electroreduction of a mixture of functionalized aromatic or heteroaromatic bromides or chlorides and allylic compounds such as acetates or carbonates in an electrochemical cell fitted with a sacrificial iron anode affords, in the presence of cobalt halide associated with pyridine as ligand in acetonitrile or DMF, the corresponding coupling product in good yields.

  在配有牺牲性铁阳极的电化学电池中，将功能化的芳族或杂芳族溴化物或氯化物与烯丙基化合物（如乙酸盐或碳酸盐）的混合物进行电还原，可在乙腈或DMF中与吡啶结合的卤化钴与配体结合时，得到相应的偶联产物，收率很高。
• Synthesis of Fluorine-Containing Phosphodiesterase 10A (PDE10A) Inhibitors and the In Vivo Evaluation of F-18 Labeled PDE10A PET Tracers in Rodent and Nonhuman Primate
  作者：Junfeng Li、Xiang Zhang、Hongjun Jin、Jinda Fan、Hubert Flores、Joel S. Perlmutter、Zhude Tu

  DOI：10.1021/acs.jmedchem.5b01205

  日期：2015.11.12

  A series of fluorine-containing PDE10A inhibitors were designed and synthesized to improve the metabolic stability of [C-11]MP-10. Twenty of the 22 new analogues had high potency and selectivity for PDE10A: 18a-j, 19d-j, 20a-b, and 21b had IC50 values <5 nM for PDE10A. Seven F-18 labeled compounds [F-18](18)a-e, [F-18]18g, and [F-18]20a were radiosynthesized by F-18-introduction onto the quinoline rather than the pyrazole moiety of the MP-10 pharmacophore and performed in vivo evaluation. Biodistribution studies in rats showed similar to 2-fold higher activity in the PDE10A-enriched striatum than nontarget brain regions; this ratio increased from 5 to 30 min postinjection, particularly for [F-18]18a-d and [F-18]20a. Micro-PET studies of [F-18]18d and [F-18]20a in nonhuman primates provided clear visualization of striatum with suitable equilibrium kinetics and favorable metabolic stability. These results suggest this strategy may identify a F-18-labeled PET tracer for quantifying the levels of PDE10A in patients with CNS disorders including Huntington's disease and schizophrenia.