1-(2,4-dimethoxy-5-(1-ethylpiperidin-4-yl)phenyl)ethanone | 958453-86-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(2,4-dimethoxy-5-(1-ethylpiperidin-4-yl)phenyl)ethanone
• CAS: 958453-86-6
• 化学式: C₁₇H₂₅NO₃
• 分子量: 291.39
• InChiKey: BPKPMZVNQLFDNL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.11
• 重原子数：
  21.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  38.77
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  1-(2,4-dimethoxy-5-(1-ethylpiperidin-4-yl)phenyl)ethanone 、 2-氯苯甲醛 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以68%的产率得到(E)-3-(2-chlorophenyl)-1-[5-(1-ethylpiperidin-4-yl)-2,4-dimethoxyphenyl]prop-2-en-1-one
  参考文献：
  名称：

  Antiproliferative activity of chalcones with basic functionalities

  摘要：

  A library of chalcones with different basic groups were synthesized and evaluated for antiproliferative activities against the human breast cancer (MCF 7) and colon cancer (HCT 116) cell lines. Structure-activity relationships were analyzed by projection methods (PCA/PLS) and multiple linear regression. Polar volume, hydrogen bonding features, HOMO energies, and charge on the carbon were found to be important factors. A basic group on either ring A or B of the chalcone led to a favourable increase in polar Volume, but when present on ring B, it increased HOMO energies and decreased the positive charge on the carbon, both of which led to lower activity. Several examples showed that final activity of the chalcone was influenced by compensatory interactions among these parameters. In general, a single basic group on ring A was associated with good activity. A notable exception was compound 1-123 which had basic groups on both rings A and B but Still maintained a good activity profile with IC50 < 10 PM and selectivity ratios >2.5. There was some evidence to show that structural differences in chalcones influenced not only activity but mechanism of action. Compounds 6-130 and 7-140 which had basic groups on ring A interfered with cell cycle progression, but the dibasic chalcone 1-123 had no effect. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.07.042
• 作为产物：
  描述：

  1-ethyl-4-(2,4-dimethoxyphenyl)piperidine 、 乙酸酐 在 三氟化硼-二甲醚络合物 作用下， 以 二氯甲烷 为溶剂， 生成 1-(2,4-dimethoxy-5-(1-ethylpiperidin-4-yl)phenyl)ethanone
  参考文献：
  名称：

  Antiproliferative activity of chalcones with basic functionalities

  摘要：

  A library of chalcones with different basic groups were synthesized and evaluated for antiproliferative activities against the human breast cancer (MCF 7) and colon cancer (HCT 116) cell lines. Structure-activity relationships were analyzed by projection methods (PCA/PLS) and multiple linear regression. Polar volume, hydrogen bonding features, HOMO energies, and charge on the carbon were found to be important factors. A basic group on either ring A or B of the chalcone led to a favourable increase in polar Volume, but when present on ring B, it increased HOMO energies and decreased the positive charge on the carbon, both of which led to lower activity. Several examples showed that final activity of the chalcone was influenced by compensatory interactions among these parameters. In general, a single basic group on ring A was associated with good activity. A notable exception was compound 1-123 which had basic groups on both rings A and B but Still maintained a good activity profile with IC50 < 10 PM and selectivity ratios >2.5. There was some evidence to show that structural differences in chalcones influenced not only activity but mechanism of action. Compounds 6-130 and 7-140 which had basic groups on ring A interfered with cell cycle progression, but the dibasic chalcone 1-123 had no effect. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.07.042