N-methyl-4-(2,4-dimethoxyphenyl)piperidine | 872057-19-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: N-methyl-4-(2,4-dimethoxyphenyl)piperidine
• 英文别名: 4-(2,4-Dimethoxyphenyl)-1-methylpiperidine
• CAS: 872057-19-7
• 化学式: C₁₄H₂₁NO₂
• 分子量: 235.326
• InChiKey: YOTTWZVXECBWSE-UHFFFAOYSA-N

物化性质

• 沸点：
  329.1±42.0 °C(Predicted)
• 密度：
  1.024±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  21.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-methyl-4-(2,4-dimethoxyphenyl)piperidine 在 sodium hydroxide 、 三氟化硼-二甲醚络合物 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 12.0h， 生成 (E)-1-[2,4-dimethoxy-5-(1-methylpiperidin-4-yl)phenyl]-3-phenylprop-2-en-1-one
  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
• 作为产物：
  描述：

  N-甲基-4-哌啶酮 在 palladium on activated charcoal 盐酸 、 氢气 、 溶剂黄146 作用下， 以 水 为溶剂， 20.0~100.0 ℃ 、275.79 kPa 条件下， 反应 3.0h， 生成 N-methyl-4-(2,4-dimethoxyphenyl)piperidine
  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

文献信息

• Proline derivatives and use thereof as drugs
  申请人：Mitsubishi Tanabe Pharma Corporation

  公开号：EP1930319A1

  公开（公告）日：2008-06-11

  The present invention aims at providing compounds having therapeutic effects due to a DPP-IV inhibitory action, and satisfactory as pharmaceutical products. The present inventors have found that derivatives having a substituent introduced into the γ-position of proline represented by the formula (I) wherein each symbol is as defined in the specification, have a potent DPP-IV inhibitory activity, and completed the present invention by increasing the stability.

  本发明旨在提供因具有 DPP-IV 抑制作用而具有治疗效果的化合物，并提供令人满意的药物产品。 本发明者发现，在式 (I) 所代表的脯氨酸的 γ 位上引入取代基的衍生物 其中各符号如说明书中所定义，具有强效的 DPP-IV 抑制活性，并通过提高稳定性完成了本发明。