2-methoxymethyl-3-bromopredicentrine | 1367181-80-3

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 阿朴菲
• 英文名称: 2-methoxymethyl-3-bromopredicentrine
• CAS: 1367181-80-3
• 化学式: C₂₂H₂₆BrNO₅
• 分子量: 464.356
• InChiKey: QLGXKMMTAUTDPJ-HNNXBMFYSA-N

物化性质

• 沸点：
  540.5±50.0 °C(predicted)
• 密度：
  1.350±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.21
• 重原子数：
  29.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  49.39
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  二氧化碳 、 2-methoxymethyl-3-bromopredicentrine 在 正丁基锂 、 盐酸 作用下， 以 四氢呋喃 、 水 、 异丙醇 为溶剂， 反应 18.17h， 以53%的产率得到3-carboxipredicentrine hydrochloride
  参考文献：
  名称：

  Towards a more selective analogue of oxaliplatin: Synthesis of [Pt((1R,2R)-diaminocyclohexane)(3-carboxypredicentrinato)]

  摘要：

  A novel oxaliplatin analogue, [Pt((1R,2R)-diaminocyclohexane)(3-carboxypredicentrinato)], boldiplatin, has been synthesized by the coordination of the boldine derivative 3-carboxypredicentrinate to the corresponding platinum(II) moiety in 5.8% overall yield. The complex was fully characterized and biologically evaluated in vitro. Boldiplatin was compared with its parent drug oxaliplatin, showing equal activity over four human tumor cell lines (MCF-7, MDA-MB-231, PC-3 and HT-29) and a tenfold decrease in toxicity over a non-tumor cell line (DHF). This selectivity makes boldiplatin a good candidate for further evaluations to assess its potential as antitumor drug. (C) 2011 Elsevier B. V. All rights reserved.

  DOI：

  10.1016/j.ica.2011.12.013
• 作为产物：
  描述：

  (6aS)-5,6,6a,7-四氢-1,9,10-三甲氧基-6-甲基-4H-二苯并[de,g]喹啉-2-醇 在 N-溴代丁二酰亚胺(NBS) 、 sodium hydroxide 作用下， 以 水 、 三氟乙酸 为溶剂， 反应 4.0h， 生成 2-methoxymethyl-3-bromopredicentrine
  参考文献：
  名称：

  Towards a more selective analogue of oxaliplatin: Synthesis of [Pt((1R,2R)-diaminocyclohexane)(3-carboxypredicentrinato)]

  摘要：

  A novel oxaliplatin analogue, [Pt((1R,2R)-diaminocyclohexane)(3-carboxypredicentrinato)], boldiplatin, has been synthesized by the coordination of the boldine derivative 3-carboxypredicentrinate to the corresponding platinum(II) moiety in 5.8% overall yield. The complex was fully characterized and biologically evaluated in vitro. Boldiplatin was compared with its parent drug oxaliplatin, showing equal activity over four human tumor cell lines (MCF-7, MDA-MB-231, PC-3 and HT-29) and a tenfold decrease in toxicity over a non-tumor cell line (DHF). This selectivity makes boldiplatin a good candidate for further evaluations to assess its potential as antitumor drug. (C) 2011 Elsevier B. V. All rights reserved.

  DOI：

  10.1016/j.ica.2011.12.013