1-(2-methyl-6-(p-methoxyphenyl)pyridin-3-yl)ethanone | 51080-14-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 1-(2-methyl-6-(p-methoxyphenyl)pyridin-3-yl)ethanone
• 英文别名: 1-(6-(4-methoxyphenyl)-2-methylpyridin-3-yl)ethan-1-one；2-Methyl-3-acetyl-6-p-anisylpyridin；1-[6-(4-methoxy-phenyl)-2-methyl-pyridin-3-yl]-ethanone；1-(6-(4-Methoxyphenyl)-2-methylpyridin-3-yl)ethanone；1-[6-(4-methoxyphenyl)-2-methylpyridin-3-yl]ethanone
• CAS: 51080-14-9
• 化学式: C₁₅H₁₅NO₂
• 分子量: 241.29
• InChiKey: QBOYYRNZYAEQHJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  39.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(2-methyl-6-(p-methoxyphenyl)pyridin-3-yl)ethanone 在 ammonium acetate 、 一水合肼 、 溶剂黄146 作用下， 以 5,5-dimethyl-1,3-cyclohexadiene 、 乙醇 为溶剂， 反应 14.0h， 生成 2-(6-(4-methoxyphenyl)-2-methylnicotinoyl)-N-phenylhydrazine-1-carbothioamide
  参考文献：
  名称：

  某些与芳基（硫代）氨基脲共轭的芳基烟酸的合成，体外生物学评估和计算机模拟研究

  摘要：

  在这里，我们介绍新的化合物，作为芳基烟酸与芳基（硫代）氨基脲衍生物的共轭物。基于结构指导的方法，它们被设计成通过靶向利什曼原虫主要蝶啶还原酶1（Lm -PTR1）的抗叶酸机制而具有抗利什曼病的活性。对于许多硫代氨基脲衍生物，其体外抗前鞭毛体和抗鞭毛体的活性是有希望的，并且优于参比米替福星。与参比miltefosine（IC 50）相比，活性最高的化合物8i和8j表现出其抗鞭毛的活性，IC 50值分别为4.2和3.3μM。值7.3）。它们的抗叶酸机制是通过叶酸和亚叶酸逆转这些化合物的抗Leishmanial活性的能力来证实的，与Lm -PTR1抑制剂甲氧苄啶相当。有趣的是，最活性化合物的体外细胞毒性试验显示出比米替福辛更高的选择性指数，强调了它们对哺乳动物细胞的安全性。此外，以Lm -PTR1作为推定目标的对接实验使体外抗利什曼原虫活性合理化。将在硅片预测显示最具活性的化合物具有良好的药代动

  DOI：

  10.1016/j.ejmech.2019.06.051
• 作为产物：
  描述：

  3-(二甲基氨基)-1-(4-甲氧基苯基)-2-丙烯-1-酮 、 乙酰丙酮 在 乙酸铵 、 K5 作用下， 反应 1.0h， 以86%的产率得到1-(2-methyl-6-(p-methoxyphenyl)pyridin-3-yl)ethanone
  参考文献：
  名称：

  A highly efficient regioselective one-pot synthesis of 2,3,6-trisubstituted pyridines and 2,7,7-trisubstituted tetrahydroquinolin-5-ones using K5CoW12O40·3H2O as a heterogeneous recyclable catalyst

  摘要：

  A systematic investigation into the regioselective one-pot, three-component condensation of enaminones la-g, beta-dicarbonyl compounds 2a-c, and ammonium acetate in the presence of a catalytic amount of K5CoW12O40 center dot 3H(2)O (0.01 equiv or 1.0 mol %) under solvent free conditions, as well as in refluxing isopropanol, has been reported. The reaction was highly efficient to produce 2,3,6-trisubstituted pyridines 3a-g, 4a-g, and novel 2,7,7-trisubstituted-5,6,7,8-tetrahydroquinoline-5-ones 5a-g in excellent yields. The present procedure offers advantages of short reaction time, simple work-up, and the catalyst exhibited remarkable reusable activity. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.10.014

文献信息

• Cu-Catalyzed Three-Component Cascade Annulation Reaction: An Entry to Functionalized Pyridines
  作者：Huanfeng Jiang、Jidan Yang、Xiaodong Tang、Jianxiao Li、Wanqing Wu

  DOI：10.1021/acs.joc.5b01621

  日期：2015.9.4

  A concise copper-catalyzed N-O bond cleavage/C-C/C-N bond formation procedure has been described for the synthesis of multisubstituted pyridines. Various oxime acetates, activated methylene compounds, and a wide range of aldehydes bearing aryl, heteroaryl, vinyl, and trifluoromethyl groups were employed to provide the tri- or tetrasubstituted pyridines with flexible substitution patterns. Moreover, this method features inexpensive catalysts, no need for extra oxidant, and high step-enconomy, which make it pratical and attractive.
• A highly efficient regioselective one-pot synthesis of 2,3,6-trisubstituted pyridines and 2,7,7-trisubstituted tetrahydroquinolin-5-ones using K5CoW12O40·3H2O as a heterogeneous recyclable catalyst
  作者：Srinivas Kantevari、Mahankhali Venu Chary、Srinivasu V.N. Vuppalapati

  DOI：10.1016/j.tet.2007.10.014

  日期：2007.12

  A systematic investigation into the regioselective one-pot, three-component condensation of enaminones la-g, beta-dicarbonyl compounds 2a-c, and ammonium acetate in the presence of a catalytic amount of K5CoW12O40 center dot 3H(2)O (0.01 equiv or 1.0 mol %) under solvent free conditions, as well as in refluxing isopropanol, has been reported. The reaction was highly efficient to produce 2,3,6-trisubstituted pyridines 3a-g, 4a-g, and novel 2,7,7-trisubstituted-5,6,7,8-tetrahydroquinoline-5-ones 5a-g in excellent yields. The present procedure offers advantages of short reaction time, simple work-up, and the catalyst exhibited remarkable reusable activity. (c) 2007 Elsevier Ltd. All rights reserved.
• Synthesis, in vitro biological evaluation and in silico studies of certain arylnicotinic acids conjugated with aryl (thio)semicarbazides as a novel class of anti-leishmanial agents
  作者：Wagdy M. Eldehna、Hadia Almahli、Tamer M. Ibrahim、Mohamed Fares、Tarfah Al-Warhi、Frank M. Boeckler、Adnan A. Bekhit、Hatem A. Abdel-Aziz

  DOI：10.1016/j.ejmech.2019.06.051

  日期：2019.10

  Herein we introduce new compounds as conjugates of arylnicotinic acids with aryl (thio)semicarbazide derivatives. Based on a structure-guided approach, they were designed to possess anti-leishmanial activity through anti-folate mechanism, via targeting Leishmania major pteridine reductase 1 (Lm-PTR1). The in vitro anti-promastigote and anti-amastigote activity were promising for many thiosemicarbazide

  在这里，我们介绍新的化合物，作为芳基烟酸与芳基（硫代）氨基脲衍生物的共轭物。基于结构指导的方法，它们被设计成通过靶向利什曼原虫主要蝶啶还原酶1（Lm -PTR1）的抗叶酸机制而具有抗利什曼病的活性。对于许多硫代氨基脲衍生物，其体外抗前鞭毛体和抗鞭毛体的活性是有希望的，并且优于参比米替福星。与参比miltefosine（IC 50）相比，活性最高的化合物8i和8j表现出其抗鞭毛的活性，IC 50值分别为4.2和3.3μM。值7.3）。它们的抗叶酸机制是通过叶酸和亚叶酸逆转这些化合物的抗Leishmanial活性的能力来证实的，与Lm -PTR1抑制剂甲氧苄啶相当。有趣的是，最活性化合物的体外细胞毒性试验显示出比米替福辛更高的选择性指数，强调了它们对哺乳动物细胞的安全性。此外，以Lm -PTR1作为推定目标的对接实验使体外抗利什曼原虫活性合理化。将在硅片预测显示最具活性的化合物具有良好的药代动