(1R,3S)-2-[4,6-bis-(4-methylpiperazin-1-yl)-[1,3,5]-triazin-2-yl]-1-(4-methoxyphenyl)-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid methyl ester | 1230643-97-6

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 哈马拉生物碱
• 英文名称: (1R,3S)-2-[4,6-bis-(4-methylpiperazin-1-yl)-[1,3,5]-triazin-2-yl]-1-(4-methoxyphenyl)-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid methyl ester
• 英文别名: methyl (1R,3S)-2-[4,6-bis(4-methylpiperazin-1-yl)-1,3,5-triazin-2-yl]-1-(4-methoxyphenyl)-1,3,4,9-tetrahydropyrido[3,4-b]indole-3-carboxylate
• CAS: 1230643-97-6
• 化学式: C₃₃H₄₁N₉O₃
• 分子量: 611.747
• InChiKey: BLEKHENMFCIHBA-LMSSTIIKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  45
• 可旋转键数：
  7
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  106
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  N-甲基哌嗪 、 在 potassium carbonate 作用下， 以 四氢呋喃 为溶剂， 生成 (1R,3S)-2-[4,6-bis-(4-methylpiperazin-1-yl)-[1,3,5]-triazin-2-yl]-1-(4-methoxyphenyl)-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid methyl ester
  参考文献：
  名称：

  Synthesis and cytotoxicity evaluation of (tetrahydro-β-carboline)-1,3,5-triazine hybrids as anticancer agents

  摘要：

  A series of tetrahydro-beta-carbolines and 1,3,5-triazine hybrids have been synthesized and evaluated for their cytotoxicity against a panel of eight human cancer cell lines and normal human fibroblasts (NIH3T3). It led us to discovery of racemic compounds 69, 71 and 75, which are selectively cytotoxic towards KB (oral cancer) cell line with IC(50) values of 1058, 664 7 and 122.2 nM, respectively, while their enantiopure forms are less active and not selective. Enantiopure compound 42 showed 2 5 times more selectivity towards MCF7 cells over normal fibroblast NIH3T3 cells with an IC(50) value of 740 nM, also arrests cell cycle in G(1) phase and induces apoptosis in MCF7 and MDA MB231cell lines.

  DOI：

  10.1016/j.ejmech.2010.02.001