5-methyl-7,13-dioxo-12,13-dihydro-7H-12-aza-5-azonia-indeno[1,2-b]phenanthrene iodide | 1129983-77-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 5-methyl-7,13-dioxo-12,13-dihydro-7H-12-aza-5-azonia-indeno[1,2-b]phenanthrene iodide
• 英文别名: N-methylcalothrixin B；20-methyl-10-aza-20-azoniapentacyclo[11.8.0.03,11.04,9.014,19]henicosa-1(13),3(11),4,6,8,14,16,18,20-nonaene-2,12-dione;iodide
• CAS: 1129983-77-2
• 化学式: C₂₀H₁₃N₂O₂*I
• 分子量: 440.24
• InChiKey: NJAQPQNEIVRGSM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.08
• 重原子数：
  25
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  53.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  calothrixin B 、 碘甲烷 反应 240.0h， 以65%的产率得到5-methyl-7,13-dioxo-12,13-dihydro-7H-12-aza-5-azonia-indeno[1,2-b]phenanthrene iodide
  参考文献：
  名称：

  Calothrixins, a New Class of Human DNA Topoisomerase I Poisons

  摘要：

  Calothrixins A (1) and B (2) were converted to their O- and N-methylated derivatives, respectively. All four compounds were found to act as poisons of DNA topoisomerase I and to do so reversibly. Three of the calothrixins (1-3) were tested for their cytotoxicity toward cultured (p53 proficient) CEM leukemia cells and found to exhibit IC50 values ranging from 0.20 to 5.13 mu M. The cell cycle effects of calothrixins 1-3 were also studied. Calothrixin B (2) produced G(1) arrest at 0.1 mu M concentration, while higher concentrations of calothrixins 1 and 3 resulted in cell accumulation in both the S and G(2)/M phases of the cell cycle. The cell cycle effects produced by the calothrixins were more readily reversible upon removal of the compounds than those produced by camptothecin.

  DOI：

  10.1021/np8007232

文献信息

• Calothrixins, a New Class of Human DNA Topoisomerase I Poisons
  作者：Qasim A. Khan、Jun Lu、Sidney M. Hecht

  DOI：10.1021/np8007232

  日期：2009.3.27

  Calothrixins A (1) and B (2) were converted to their O- and N-methylated derivatives, respectively. All four compounds were found to act as poisons of DNA topoisomerase I and to do so reversibly. Three of the calothrixins (1-3) were tested for their cytotoxicity toward cultured (p53 proficient) CEM leukemia cells and found to exhibit IC50 values ranging from 0.20 to 5.13 mu M. The cell cycle effects of calothrixins 1-3 were also studied. Calothrixin B (2) produced G(1) arrest at 0.1 mu M concentration, while higher concentrations of calothrixins 1 and 3 resulted in cell accumulation in both the S and G(2)/M phases of the cell cycle. The cell cycle effects produced by the calothrixins were more readily reversible upon removal of the compounds than those produced by camptothecin.