4-(5-acetyl-2,4-dimethoxyphenyl)-1-methylpiperidine | 872057-20-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-(5-acetyl-2,4-dimethoxyphenyl)-1-methylpiperidine
• 英文别名: 1-(2,4-dimethoxy-5-(1-methylpiperidin-4-yl)phenyl)ethanone；1-[2,4-dimethoxy-5-(1-methylpiperidin-4-yl)phenyl]ethanone
• CAS: 872057-20-0
• 化学式: C₁₆H₂₃NO₃
• 分子量: 277.364
• InChiKey: DWMXIFKZRKMMTF-UHFFFAOYSA-N

物化性质

• 熔点：
  181-182 °C(Solv: methanol (67-56-1); water (7732-18-5))
• 沸点：
  410.9±45.0 °C(Predicted)
• 密度：
  1.061±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.72
• 重原子数：
  20.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 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：

  4-(5-acetyl-2,4-dimethoxyphenyl)-1-methylpiperidine 、 邻甲氧基苯甲醛 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以80%的产率得到(E)-1-[2,4-dimethoxy-5-(1-methylpiperidin-4-yl)phenyl]-3-(2-methoxyphenyl)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：

  N-甲基-4-哌啶酮 在 palladium on activated charcoal 盐酸 、 三氟化硼-二甲醚络合物 、 氢气 、 溶剂黄146 作用下， 以 二氯甲烷 、 水 为溶剂， 20.0~100.0 ℃ 、275.79 kPa 条件下， 反应 3.0h， 生成 4-(5-acetyl-2,4-dimethoxyphenyl)-1-methylpiperidine
  参考文献：
  名称：

  Antiproliferative properties of piperidinylchalcones

  摘要：

  Methoxylated chalcones bearing N-methylpiperidinyl substituents oil ring A inhibited the growth of human tumour cell lines (MCF, HCT 116, and Jurkat) at IC50 values or < 5 mu M. Investigations oil a representative member (12) showed that antiproliferative activity was linked to the disruption of the cell cycle at G1 and G2/M phases. The effect was concentration dependent and was evident at the approximate IC50 of 12. Down regulation of cell cycle regulatory components (CDK4, cyclin B, E2F, and phosphorylated Rb) were observed under similar conditions. Methoxylated chalconcs without the piperidinyl substituent were found to exert equally potent and selective antiproliferative activity against HCT 116 tumour cells but did not interfere with cell cycle progression at their IC50 concentrations. The presence of the piperidinyl substituent in the chalcone template is proposed to lend specificity to the mechanism of antiproliferative activity, in addition to promoting a more desirable physicochemical profile. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.08.006