4-(piperidin-1-yl)-2-methylquinoline | 82607-86-1

• 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: 4-(piperidin-1-yl)-2-methylquinoline
• 英文别名: 2-methyl-4-(piperidin-1-yl)quinoline；2-methyl-4-piperidin-1-ylquinoline
• CAS: 82607-86-1
• 化学式: C₁₅H₁₈N₂
• mdl: MFCD28336472
• 分子量: 226.321
• InChiKey: YBJCWVOLJLXONB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  16.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(piperidin-1-yl)-2-methylquinoline 在 selenium(IV) oxide 作用下， 以 1,4-二氧六环 为溶剂， 以96 %的产率得到4-(piperidin-1-yl)quinoline-2-carbaldehyde
  参考文献：
  名称：

  使用喹啉官能化 NHC 作为定向和官能化基团，Ru/O2 催化氧化 C–H 活化/炔环化

  摘要：

  钌/O 2催化咪唑并[1,5- a ]喹啉-2-鎓盐与炔烃通过N-杂环卡宾引导的C-H活化发生氧化成环反应，得到π-共轭稠合咪唑[1,5-报道了a ]喹啉-2-鎓衍生物。分子氧已被探索作为一种经济且清洁的氧化剂以及金属氧化剂的替代品。当前的协议展示了广泛的底物范围，包括生物活性 (±)-α-生育酚衍生物。此外，大多数环状产品表现出很强的荧光特性，表明它们具有制造新型发光材料的潜力。

  DOI：

  10.1021/acs.orglett.4c00542
• 作为产物：
  描述：

  4-羟基-2-甲基喹啉 在 对甲苯磺酸 、 三氯氧磷 作用下， 反应 12.0h， 生成 4-(piperidin-1-yl)-2-methylquinoline
  参考文献：
  名称：

  Design, synthesis, and biological evaluation of 2-arylethenylquinoline derivatives as multifunctional agents for the treatment of Alzheimer's disease

  摘要：

  A series of new 2-arylethenylquinoline derivatives (4a(1)-4a(12), 4b(1)-4b(8), 4c(1)-4c(4), 4d(1)-4d(3) and 4e(1)-4e(9)) were designed, synthesized, and evaluated as potential multifunctional agents for the treatment of Alzheimer's disease (AD). In vitro studies showed that these synthetic compounds inhibited self-induced A beta(1-42) aggregation effectively ranged from 23.6% to 83.9% at the concentration of 20 mu M, and acted as potential antioxidants and biometal chelators. Their structure-activity relationships were obtained and discussed. In particular, compound 4b(1), the most active compound, displayed strong inhibitory activity with an IC50 value of 9.7 mu M for self-induced A beta(1-42) aggregation, good antioxidative activity with a value of 3.9-fold of Trolox, potent inhibitory activity for cholinesterase with IC50 values of 0.2 mu M and 64.1 mu M against butyrylcholinesterase (BuChE) and acetylcholinesterase (AChE), respectively. Besides, 4b(1) was also capable of disassembling the self-induced A beta(1-42) aggregation fibrils with a ratio of 59.8% at 20 mu M concentration, and had a good metal chelating activity. Taken together, these results suggest that compound 4b(1) might be a promising lead compound for AD treatment. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.10.018

文献信息

• Developing Inhibitors of the p47phox–p22phox Protein–Protein Interaction by Fragment-Based Drug Discovery
  作者：Sara Marie Øie Solbak、Jie Zang、Dilip Narayanan、Lars Jakobsen Høj、Saskia Bucciarelli、Charlotte Softley、Sebastian Meier、Annette Eva Langkilde、Charlotte Held Gotfredsen、Michael Sattler、Anders Bach

  DOI：10.1021/acs.jmedchem.9b01492

  日期：2020.2.13

  Nicotinamide adenine dinucleotide phosphate oxidase isoform 2 is an enzyme complex, which generates reactive oxygen species and contributes to oxidative stress. The p47phox-p22phox interaction is critical for the activation of the catalytical NOX2 domain, and p47phox is a potential target for therapeutic intervention. By screening 2500 fragments using fluorescence polarization and a thermal shift assay and validation by surface plasmon resonance, we found eight hits toward the tandem SH3 domain of p47phox (p47phox(SH3A-B)) with K-D values of 400-600 mu M. Structural studies revealed that fragments 1 and 2 bound two separate binding sites in the elongated conformation of p47phox(SH3A-B) and these competed with p22phox for binding to p47phox(SH3A-B). Chemical optimization led to a dimeric compound with the ability to potently inhibit the p47phox(SH3A-B)-p22phox interaction (K-i of 20 mu M). Thereby, we reveal a new way of targeting p47phox and present the first report of drug-like molecules with the ability to bind p47phox and inhibit its interaction with p22phox.
• Microwave-Assisted Efficient Synthesis of 4-Substituted Amino-2-methylquinolines Catalyzed by p-Toluenesulfonic Acid
  作者：Xiao-qin Wang、Wen-jia Pan、Yuan-hong Cai、Xiao-yang Xie、Cui-ying Huang、Jia-yu Li、Wen-na Chen、Ming-hua He

  DOI：10.3987/com-16-13516

  日期：——

  A series of novel 4-subtituted amino-2-methylquinolines (3a-3o) were readily synthesized via the reaction of 4-chloro-2-methylquinoline with amines catalyzed by p-toluenesulfonic acid (TsoH) at 120 degrees C for 1 h under microwave-assisted organic synthesis (MAOS) condition. The yields of products 3a-3o were in range of 55-89%. This approach has advantages such as higher yield, shorter reaction time, lower costs, more convenience, and higher efficiency compared to the conventional method. The structures of the products were characterized by using H-1 NMR, C-13 NMR and HRMS. The reactivity of different amines was discussed.
• Discovery of Small Molecules for Up-Regulating the Translation of Antiamyloidogenic Secretase, a Disintegrin and Metalloproteinase 10 (ADAM10), by Binding to the G-Quadruplex-Forming Sequence in the 5′ Untranslated Region (UTR) of Its mRNA
  作者：Jie Dai、Zhen-Quan Liu、Xiao-Qin Wang、Jing Lin、Pei-Fen Yao、Shi-Liang Huang、Tian-Miao Ou、Jia-Heng Tan、Ding Li、Lian-Quan Gu、Zhi-Shu Huang

  DOI：10.1021/acs.jmedchem.5b00139

  日期：2015.5.14

  Up-regulation of a disintegrin and metalloptoteinase 10 (ADAM10) to prevent the formation of beta-amyloid (A beta) peptides might be a promising strategy to treat Alzheimer's disease (AD). RNA G-quadruplex motif within the 5'-UTR of the ADAM10 mRNA is an inhibitory element for ADAM10 translation. Thus, mitigation of the suppressive effect of this motif using an RNA G-quadruplex-forming G-rich sequence (QGRS) binder might be a new approach for AD therapy. Herein, a series of new methylquinolinium derivatives were synthesized and screened by surface plasmon resonance (SPR) and the dual-luciferase reporter assay. Among them, compound 24 showed selective affinity for the QGRS of ADAM10 and could strongly up-regulate the translation of it. Moreover, treatment with 24 led to a significant increase of the secretion of sAPP alpha, consequently decreasing the A beta(40) in cellular. These results illustrate that the ititeraction between the RNA QGRS and a small molecule may be a new molecular strategy to modulate the translation of ADAM10.
• CLXXVI.—Attempts to find new antimalarials. Part V. Some piperidino- and piperazino-derivatives of quinoline
  作者：William Ogilvie Kermack、James Fergus Smith

  DOI：10.1039/jr9300001356

  日期：——
• Katayanagi, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1948, vol. 68, p. 133,135
  作者：Katayanagi

  DOI：——

  日期：——