9-O-2-(1-piperidinyl)ethylberberine chloride | 1462359-83-6

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 原小檗碱生物碱及其衍生物
• 英文名称: 9-O-2-(1-piperidinyl)ethylberberine chloride
• 英文别名: 17-Methoxy-16-(2-piperidin-1-ylethoxy)-5,7-dioxa-13-azoniapentacyclo[11.8.0.02,10.04,8.015,20]henicosa-1(13),2,4(8),9,14,16,18,20-octaene;chloride；17-methoxy-16-(2-piperidin-1-ylethoxy)-5,7-dioxa-13-azoniapentacyclo[11.8.0.02,10.04,8.015,20]henicosa-1(13),2,4(8),9,14,16,18,20-octaene;chloride
• CAS: 1462359-83-6
• 化学式: C₂₆H₂₉N₂O₄*Cl
• 分子量: 468.98
• InChiKey: RYLSUALIAQVXFQ-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  0.96
• 重原子数：
  33
• 可旋转键数：
  5
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  44
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  盐酸小檗碱 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 80.0~190.0 ℃ 、4.0 kPa 条件下， 反应 0.33h， 生成 9-O-2-(1-piperidinyl)ethylberberine chloride
  参考文献：
  名称：

  Synthesis, cytotoxicity, and DNA-binding property of berberine derivatives

  摘要：

  9-Substituted berberine derivatives (4a-4f) with polyethylene glycol side chain and terminal group were synthesized and characterized by elemental (C, H, and N) and spectral analysis (NMR, HRMS and FTIR). These compounds were tested for their in vitro cytotoxic activity against four human tumor cell lines: granulocyte leukemia (HL-60), gastrocarcinoma (BGC-823), carcinoma (Bel-7402), and nasopharyngeal carcinoma (KB) by the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay. The DNA-binding properties were investigated by UV-Vis absorption, fluorescence, CD spectroscopies, and thermal denaturation measurements. The results indicated that 4a-4f exerted cytotoxic effects with selectivity against tested cell lines. 4a exhibited higher cytotoxicity than cisplatin, berberine, and berberrubine against HL-60 and BGC-823 cell lines. The length of side chains and nature of terminal groups played an important role in the cytotoxicity. Berberine derivatives binded to CT-DNA in an intercalating mode. The binding affinities decreased with the increasing length of side chains. Compounds 4a-4c and 4e could change the DNA conformation from B to A-like form.

  DOI：

  10.1007/s00044-013-0796-9

文献信息

• Synthesis, cytotoxicity, and DNA-binding property of berberine derivatives
  作者：Cui Liu、Siyuan Liu、Yuechai Wang、Shuxiang Wang、Jinchao Zhang、Shenghui Li、Xinying Qin、Xiaoliu Li、Kerang Wang、Quoqiang Zhou

  DOI：10.1007/s00044-013-0796-9

  日期：2014.4

  9-Substituted berberine derivatives (4a-4f) with polyethylene glycol side chain and terminal group were synthesized and characterized by elemental (C, H, and N) and spectral analysis (NMR, HRMS and FTIR). These compounds were tested for their in vitro cytotoxic activity against four human tumor cell lines: granulocyte leukemia (HL-60), gastrocarcinoma (BGC-823), carcinoma (Bel-7402), and nasopharyngeal carcinoma (KB) by the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay. The DNA-binding properties were investigated by UV-Vis absorption, fluorescence, CD spectroscopies, and thermal denaturation measurements. The results indicated that 4a-4f exerted cytotoxic effects with selectivity against tested cell lines. 4a exhibited higher cytotoxicity than cisplatin, berberine, and berberrubine against HL-60 and BGC-823 cell lines. The length of side chains and nature of terminal groups played an important role in the cytotoxicity. Berberine derivatives binded to CT-DNA in an intercalating mode. The binding affinities decreased with the increasing length of side chains. Compounds 4a-4c and 4e could change the DNA conformation from B to A-like form.