1-(4-(2-(哌啶-1-基)乙氧基)苯基)丙烷-1-酮 | 101255-84-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1-(4-(2-(哌啶-1-基)乙氧基)苯基)丙烷-1-酮
• 英文名称: 1-(4-(2-(piperidin-1-yl)ethoxy)phenyl)propan-1-one
• 英文别名: 1-[4-(2-Piperidin-1-ylethoxy)phenyl]propan-1-one
• CAS: 101255-84-9
• 化学式: C₁₆H₂₃NO₂
• mdl: MFCD02609610
• 分子量: 261.364
• InChiKey: PYULMQUYQWMIIR-UHFFFAOYSA-N

物化性质

• 沸点：
  397.8±22.0 °C(Predicted)
• 密度：
  1.039±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.562
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT

反应信息

• 作为反应物：
  描述：

  2-(4,5-二氢-4,4-二甲基-2-噁唑)苯胺 、 1-(4-(2-(哌啶-1-基)乙氧基)苯基)丙烷-1-酮 在 三氟甲磺酸 作用下， 以 正丁醇 为溶剂， 以48%的产率得到3-methyl-2-[4-[2-(1-piperidyl)ethoxy]phenyl]-1H-quinolin-4-one
  参考文献：
  名称：

  Identification, Design and Biological Evaluation of Heterocyclic Quinolones Targeting Plasmodium falciparum Type II NADH:Quinone Oxidoreductase (PfNDH2)

  摘要：

  Following a program undertaken to identify hit compounds against NADH:ubiquinone oxidoreductase (PfNDH2), a novel enzyme target within the malaria parasite Plasmodium falciparum, hit to lead optimization led to identification of CK-2-68, a molecule suitable for further development. In order to reduce ClogP and improve solubility of CK-2-68 incorporation of a variety of heterocycles, within the side chain of the quinolone core, was carried out, and this approach led to a lead compound SL-2-25 (8b). 8b has IC(50)s in the nanomolar range versus both the enzyme and whole cell P. falciparum (IC50 = 15 nM PfNDH2; IC50 = 54 nM (3D7 strain of P. falciparum) with notable oral activity of ED50/ED90 of 1.87/4.72 mg/kg versus Plasmodium berghei (NS Strain) in a murine model of malaria when formulated as a phosphate salt. Analogues in this series also demonstrate nanomolar activity against the bc(1) complex of P. falciparum providing the potential added benefit of a dual mechanism of action. The potent oral activity of 2-pyridyl quinolones underlines the potential of this template for further lead optimization studies.

  DOI：

  10.1021/jm201184h
• 作为产物：
  描述：

  1-(2-氯乙基)哌啶 、 4-羟基苯丙酮 在 乙醇 、 sodium ethanolate 作用下， 生成 1-(4-(2-(哌啶-1-基)乙氧基)苯基)丙烷-1-酮
  参考文献：
  名称：

  Najer et al., Bulletin de la Societe Chimique de France, 1956, p. 1672

  摘要：

  DOI：

文献信息

• Discovery, Optimization, and Target Identification of Novel Potent Broad-Spectrum Antiviral Inhibitors
  作者：Yiqing Yang、Lin Cao、Hongying Gao、Yue Wu、Yaxin Wang、Fang Fang、Tianlong Lan、Zhiyong Lou、Yu Rao

  DOI：10.1021/acs.jmedchem.9b00091

  日期：2019.4.25

  exploited by phenotypic screening to discover new antiviral inhibitors. After optimizations from hit to lead, a novel potent small molecule (RYL-634) was identified, showing excellent broad-spectrum inhibition activity against various pathogenic viruses, including hepatitis C virus, dengue virus, Zika virus, chikungunya virus, enterovirus 71, human immunodeficiency virus, respiratory syncytial virus

  病毒感染正在增加，并且可能是持久的全球风险。在这项研究中，通过表型筛选开发了一个化学文库，以发现新的抗病毒抑制剂。经过从头到尾的优化后，鉴定出一种新型的强效小分子（RYL-634），它对各种致病性病毒（包括丙型肝炎病毒，登革热病毒，寨卡病毒，基孔肯雅病毒，肠病毒71，人免疫缺陷病毒，呼吸道合胞病毒等。通过结合基于活性的蛋白质谱分析和其他技术，进一步探索了RYL-634的作用机理和潜在靶标。最后，人二氢乳清酸酯脱氢酶被证实是RYL-634的主要靶标。在使用RYL-634进行压力选择时，我们没有观察到任何突变抗性，并且与某些获得美国食品药品监督管理局（FDA）批准的药物具有很强的协同作用。因此，有很大的潜力开发基于RYL-634的新型广谱抗病毒药。
• SnCl4–Zn: a novel reductive system for deoxygenative coupling of aliphatic, aromatic, chalcone epoxide, and indanone carbonyl compounds to olefins
  作者：Gulab Khushalrao Pathe、Naseem Ahmed

  DOI：10.1016/j.tetlet.2015.01.194

  日期：2015.3

  SnCl4–Zn complex provided a novel reductive system in the deoxygenative cross-coupling of aliphatic, aromatic, chalcone epoxide and indanone carbonyl compounds to olefins in high yield (55–86%) at reflux temperature in THF. The advantage of this reagent is inexpensive, short reaction time, and high yield compared to the reagents used in the McMurry cross-coupling reaction.

  SnCl 4 -Zn络合物在脂肪族，芳香族，查尔酮环氧化物和茚满酮羰基化合物在THF中回流温度下，以高收率（55-86％）脱氧交叉偶联，提供了一种新颖的还原体系。与用于McMurry交叉偶联反应的试剂相比，该试剂的优点是价格便宜，反应时间短且产率高。
• 一种化合物及其在制备抗丙肝病毒药物中的 应用
  申请人：清华大学

  公开号：CN106946775B

  公开（公告）日：2020-04-10

  本发明公开了一种化合物及其在制备抗丙肝病毒药物中的应用。所述化合物的结构式如式Ⅰ或式Ⅱ所示。本发明提供的式Ⅰ所示化合物或式Ⅱ所示化合物可用于与其它抗病毒药物如干扰素(PEG IFN‑α)，利巴韦林(ribavirin,RBV)，boceprevir，telaprevir，simeprevir，sofosbuvir，daclatasvir等联合用药来制备抗HCV和其它病毒感染的产品。本发明提供的化合物，具有丰富的官能团多样性与可修饰性，产物相对易于分离纯化。本发明所提供的化合物对HCV等病毒有很好的抑制作用，这是一类通过表型筛选得到的化合物，其抗病毒机制有很大不同，该类化合物在抗病毒领域化合物结构具有极强的新颖性和创新性，之前并未见诸报道。综上所述，本发明具有广阔的发展与应用前景。
• Anti-proliferative activities of flavone–estradiol Stille-coupling adducts and of indanone-based compounds obtained by SnCl₄/Zn-catalysed McMurry cross-coupling reactions
  作者：Gulab Khushalrao Pathe、Naveen K. Konduru、Iram Parveen、Naseem Ahmed

  DOI：10.1039/c5ra15685h

  日期：——

  Flavone–estradiol adducts and indanophen based tamoxifen analogs are synthesized using SnCl₄–Zn reagent via McMurry reaction and evaluated in human cervical (HeLa) and breast cancer cells (MCF-7 and MDA-MB-231) for the anti-proliferative activity.

  使用SnCl₄–Zn试剂通过McMurry反应合成黄酮-雌二醇加合物和基于indanophen的他莫昔芬类似物，并在人宫颈癌（HeLa）和乳腺癌细胞（MCF-7和MDA-MB-231）中评估其抗增殖活性。
• Flexible Estrogen Receptor Modulators:  Design, Synthesis, and Antagonistic Effects in Human MCF-7 Breast Cancer Cells
  作者：Mary J. Meegan、Rosario B. Hughes、David G. Lloyd、D. Clive Williams、Daniela M. Zisterer

  DOI：10.1021/jm001119l

  日期：2001.3.1

  Although many series of estrogen receptor antagonists continue to be produced, the majority are direct structural analogues of existing modulators. To examine the tolerance of the estrogen receptor toward flexible ligands, a series of novel flexible estrogen receptor antagonists were prepared and their antiproliferative effects on human MCF-7 breast tumor cells investigated. Each of these compounds deviated from the traditional triphenylethylene backbone associated with common tamoxifen analogues through the introduction of a flexible methylene (benzylic) spacing group between one of the aryl rings and the ethylene group and through variations in the basic side chain moiety. The compounds prepared, when assayed in conjunction with a tamoxifen standard, demonstrated high potency in antiproliferative assays against an MCF-7 human breast cancer cell line with low cytotoxicity and high binding affinity. A computational study was undertaken to investigate the compounds ' potential interactions with specific residues within the human estrogen receptor a ligand-binding domain (ER-LBD), predicting these compounds bind in an antiestrogenic fashion within the ER-LBD and interact with those important residues previously identified in the structures of ER-LBD agonist/antagonist cocrystals. These compounds further illustrate the eclectic nature of the estrogen receptor in terms of ligand flexibility tolerance.