3-(dimethylamino)-1-(4-methoxyphenyl)-2-methyl-2-propen-1-one | 208529-38-8

• 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: 3-(dimethylamino)-1-(4-methoxyphenyl)-2-methyl-2-propen-1-one
• 英文别名: 3-(Dimethylamino)-1-(4-methoxyphenyl)-2-methylprop-2-en-1-one；3-(dimethylamino)-1-(4-methoxyphenyl)-2-methylprop-2-en-1-one
• CAS: 208529-38-8
• 化学式: C₁₃H₁₇NO₂
• 分子量: 219.283
• InChiKey: HZWQLRTZRCEFOL-UHFFFAOYSA-N

物化性质

• 沸点：
  329.8±42.0 °C(Predicted)
• 密度：
  1.035±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(dimethylamino)-1-(4-methoxyphenyl)-2-methyl-2-propen-1-one 在 吡啶 、 sodium methylate 、 三溴化硼 、 一水合肼 、 三氯氧磷 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 28.0h， 生成 Cyclopropanecarboxylic acid [6-(4-hydroxy-phenyl)-5-methyl-1H-pyrazolo[3,4-b]pyridin-3-yl]-amide
  参考文献：
  名称：

  6-Aryl-pyrazolo[3,4-b]pyridines: potent inhibitors of glycogen synthase kinase-3 (GSK-3)

  摘要：

  A novel series of 6-aryl-pyrazolo[3,4-b]pyridines has been identified that are potent inhibitors of glycogen synthase kinase-3 (GSK-3).(C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00645-0
• 作为产物：
  描述：

  N,N-二甲基甲酰胺二甲基缩醛 、 对甲氧基苯丙酮 以 5,5-dimethyl-1,3-cyclohexadiene 为溶剂， 反应 4.0h， 以69%的产率得到3-(dimethylamino)-1-(4-methoxyphenyl)-2-methyl-2-propen-1-one
  参考文献：
  名称：

  Synthesis and biological evaluation of novel pyrazole derivatives with anticancer activity

  摘要：

  We synthesized thirty-six novel pyrazole derivatives and studied their antiproliferative activity in human ovarian adenocarcinoma A2780 cells, human lung carcinoma A549 cells, and murine P388 leukemia cells.Four of these substances were selected because of their higher antiproliferative activity and further analyses showed that they were all able to induce apoptosis, although to a different extent. The expression of p53 and p21(waf1), which induce apoptosis and cell cycle arrest, was evaluated by western blot analysis in cells treated with compound 12d.The analysis of the cell cycle showed that all the selected compounds cause a partial G2/M block and the formation of polyploid cells. Furthermore, the four selected compounds were tested for their interaction with the microtubular cytoskeletal system by docking analysis, tubulin polymerization assay and immunofluorescence staining, demonstrating that the compound 12d, unlike the other active derivatives, was able to significantly bind dimers of alpha- and beta-tubulin, probably causing a molecular distortion resulting in the disassembly of microtubules. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.08.014

文献信息

• Nickel‐Catalyzed Tandem Ring Contraction of TEMPO and C−N Bond Transamination of Enaminones toward Amino Diversity of Enaminones
  作者：Haozhi Wu、Tian Luo、Jie‐Ping Wan、Jianwen Jiang、Yunyun Liu

  DOI：10.1002/ejoc.202200552

  日期：2022.7.14

  The Ni(II)-catalyzed ring contraction in TEMPO providing 2,3-dimethyl pyrrolidine as well as the capture of this species with N,N-dimethyl enaminones through transamination are realized for the practical synthesis of 2,3-dimethyl pyrrolidine functionalized enaminones for the first time.

  在 TEMPO 中 Ni(II) 催化的环收缩提供 2,3-二甲基吡咯烷，以及通过氨基转移用N,N-二甲基烯胺酮捕获该物种，实现了 2,3-二甲基吡咯烷官能化烯胺酮的实际合成首次。
• Synthesis and biological evaluation of novel pyrazole derivatives with anticancer activity
  作者：Alessandro Balbi、Maria Anzaldi、Chiara Macciò、Cinzia Aiello、Mauro Mazzei、Rosaria Gangemi、Patrizio Castagnola、Mariangela Miele、Camillo Rosano、Maurizio Viale

  DOI：10.1016/j.ejmech.2011.08.014

  日期：2011.11

  We synthesized thirty-six novel pyrazole derivatives and studied their antiproliferative activity in human ovarian adenocarcinoma A2780 cells, human lung carcinoma A549 cells, and murine P388 leukemia cells.Four of these substances were selected because of their higher antiproliferative activity and further analyses showed that they were all able to induce apoptosis, although to a different extent. The expression of p53 and p21(waf1), which induce apoptosis and cell cycle arrest, was evaluated by western blot analysis in cells treated with compound 12d.The analysis of the cell cycle showed that all the selected compounds cause a partial G2/M block and the formation of polyploid cells. Furthermore, the four selected compounds were tested for their interaction with the microtubular cytoskeletal system by docking analysis, tubulin polymerization assay and immunofluorescence staining, demonstrating that the compound 12d, unlike the other active derivatives, was able to significantly bind dimers of alpha- and beta-tubulin, probably causing a molecular distortion resulting in the disassembly of microtubules. (C) 2011 Elsevier Masson SAS. All rights reserved.
• 6-Aryl-pyrazolo[3,4-b]pyridines: potent inhibitors of glycogen synthase kinase-3 (GSK-3)
  作者：Jason Witherington、Vincent Bordas、Alessandra Gaiba、Neil S. Garton、Antoinette Naylor、Anthony D. Rawlings、Brian P. Slingsby、David G. Smith、Andrew K. Takle、Robert W. Ward

  DOI：10.1016/s0960-894x(03)00645-0

  日期：2003.9

  A novel series of 6-aryl-pyrazolo[3,4-b]pyridines has been identified that are potent inhibitors of glycogen synthase kinase-3 (GSK-3).(C) 2003 Elsevier Ltd. All rights reserved.