N-(2-acetylphenyl)pyridine-4-carboxamide | 82211-37-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(2-acetylphenyl)pyridine-4-carboxamide
• 英文别名: N-(2-acetyl-phenyl)-isonicotinamide；N-(2-acetylphenyl)isonicotinamide
• CAS: 82211-37-8
• 化学式: C₁₄H₁₂N₂O₂
• mdl: MFCD07819277
• 分子量: 240.261
• InChiKey: DUCFDYVKLQHHOW-UHFFFAOYSA-N

物化性质

• 熔点：
  119-120 °C
• 沸点：
  331.8±22.0 °C(Predicted)
• 密度：
  1.244±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.071
• 拓扑面积：
  59.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(2-acetylphenyl)pyridine-4-carboxamide 生成 N-[2-(1-hydroxyethyl)phenyl]pyridine-4-carboxamide
  参考文献：
  名称：

  SUGIYAMA, XIROSI;TAKEHUTI, MASATAKEH;TOMIOKA, XIROMI;SIRAKAVA, NORIO;OKAD+

  摘要：

  DOI：
• 作为产物：
  描述：

  异烟酸 在 氯化亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 N-(2-acetylphenyl)pyridine-4-carboxamide
  参考文献：
  名称：

  含有肼部分的新型吡唑-4-甲酰胺和芳香族甲酰胺衍生物作为潜在的 SDHI

  摘要：

  为了促进新型SDHIs杀菌剂的发现和开发，设计、合成了一系列具有肼支架的新型吡唑-4-甲酰胺4a-t和芳香族甲酰胺8a-i ，并评估了其抗真菌活性。结果表明，化合物4i对立枯丝核菌表现出优异的抗真菌活性， EC 50值为0.24 μg/mL，比啶酰菌胺（EC 50  = 0.74 μg/mL）强约3倍。此外，化合物4i还对核盘菌、灰霉病菌、交替链格孢菌和禾谷镰刀菌表现出良好的抗真菌活性（IC 50  = 1.21–4.50 μg/mL），表明具有广谱抗真菌活性。此外，体内抗真菌活性结果表明，4i在100 μg/mL浓度下可显着抑制水稻叶片中立枯丝核菌的生长，具有良好的保护效果（55.21%）和优异的疗效（73.06%）。SDH酶抑制实验结果表明，化合物4i具有显着的SDH抑制作用，IC 50值为6.47 μM，优于啶酰菌胺（IC 50  = 7.92 μM）。此外，SEM分析表明，化合物4

  DOI：

  10.1016/j.molstruc.2023.136202

文献信息

• Sequential Cu-Catalyzed Amidation-Base-Mediated Camps Cyclization:  A Two-Step Synthesis of 2-Aryl-4-quinolones from <i>o</i>-Halophenones
  作者：Carrie P. Jones、Kevin W. Anderson、Stephen L. Buchwald

  DOI：10.1021/jo701384n

  日期：2007.10.1

  two-step method for the preparation of 2-aryl- and 2-vinyl-4-quinolones that utilizes a copper-catalyzed amidation of o-halophenones followed by a base-promoted Camps cyclization of the resulting N-(2-ketoaryl)amides is described. With CuI, a diamine ligand, and base as the catalyst system, the amidation reactions proceed in good yields for a range of aryl, heteroaryl, and vinyl amides. The subsequent Camps

  对于2-芳基-和2-乙烯基-4-喹诺酮的制备直接两步法，其利用的铜催化的酰胺化ö -halophenones然后将所得的碱促进环化营ñ - （2 -ketoaryl描述了酰胺。使用CuI（一种二胺配体）和碱作为催化剂体系，对于一系列芳基，杂芳基和乙烯基酰胺，酰胺化反应的收率很高。随后的营地环化有效地提供了所描述条件的所需4-喹诺酮类药物。
• Heterocyclic and bicyclic compounds, compositions and methods
  申请人：Pal Manojit

  公开号：US20060128702A1

  公开（公告）日：2006-06-15

  The present invention provides, among other things, new bicyclo heterocyclic compounds, compositions comprising these heterocyclic compounds, methods of making the heterocyclic compounds, and methods of using these heterocyclic compounds for treating a variety of conditions and disease states associated with, for example, cellular proliferation, inflammation, glycosidase expression, or the low expression of Perlecan.

  本发明提供了新的双环杂环化合物、包含这些杂环化合物的组合物、制备这些杂环化合物的方法，以及使用这些杂环化合物治疗与细胞增殖、炎症、糖苷酶表达或Perlecan低表达等多种疾病状态相关的方法。
• Development of <i>N</i>-Methyl-(2-arylquinolin-4-yl)oxypropanamides as Leads to PET Radioligands for Translocator Protein (18 kDa)
  作者：Chad Brouwer、Kimberly Jenko、Sami S. Zoghbi、Robert B. Innis、Victor W. Pike

  DOI：10.1021/jm5007947

  日期：2014.7.24

  Translocator protein (18 kDa), known as TSPO, is a recognized biomarker of neuroinflammation. Radioligands with PET accurately quantify TSPO in neuroinflammatory conditions. However, the existence of three human TSPO genotypes that show differential affinity to almost all useful TSPO PET radioligands hampers such studies. There is an unmet need for genotype-insensitive, high-affinity, and moderately lipophilic TSPO ligands that may serve as leads for PET radioligand development. To address this need, we varied the known high-affinity TSPO ligand (l)-N,N-diethyl-2-methyl-3-(2-phenylquinolin-4-yl)propanamide in its aryl scaffold, side chain tether, and pendant substituted amido group while retaining an N-methyl group as a site for labeling with carbon-11. From this effort, oxygen-tethered N-methyl-aryloxypropanamides emerged as new high-affinity TSPO ligands with attenuated lipophilicity, including one example with attractive properties for PET radioligand development, namely N-methyl-N-phenyl-2-[2-(pyridin-2-yl)quinolin-4-yl]oxy}propanamide (22a; rat K-i = 0.10 nM; human TSPO genotypes K-i = 1.4 nM; clogD = 4.18).
• WO2006/58201
  申请人：——

  公开号：——

  公开（公告）日：——
• C-2 phenyl replacements to obtain potent quinoline-based <i>Staphylococcus aureus</i> NorA inhibitors
  作者：Tommaso Felicetti、Gianmarco Mangiaterra、Rolando Cannalire、Nicholas Cedraro、Donatella Pietrella、Andrea Astolfi、Serena Massari、Oriana Tabarrini、Giuseppe Manfroni、Maria Letizia Barreca、Violetta Cecchetti、Francesca Biavasco、Stefano Sabatini

  DOI：10.1080/14756366.2020.1719083

  日期：2020.1.1

  NorA is the most studied efflux pump of Staphylococcus aureus and is responsible for high level resistance towards fluoroquinolone drugs. Although along the years many NorA efflux pump inhibitors (EPIs) have been reported, poor information is available about structure-activity relationship (SAR) around their nuclei and reliability of data supported by robust assays proving NorA inhibition. In this regard, we focussed efforts on the 2-phenylquinoline as a promising chemotype to develop potent NorA EPIs. Herein, we report SAR studies about the introduction of different aryl moieties on the quinoline C-2 position. The new derivative 37a showed an improved EPI activity (16-fold) with respect to the starting hit 1. Moreover, compound 37a exhibited a high potential in time-kill curves when combined with ciprofloxacin against SA-1199B (norA+). Also, 37a exhibited poor non-specific effect on bacterial membrane polarisation and showed an improvement in terms of "selectivity index" in comparison to 1.