9-methylheptaphylline | 1335011-98-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 9-methylheptaphylline
• 英文别名: 2-hydroxy-9-methyl-1-(3-methylbut-2-enyl)carbazole-3-carbaldehyde
• CAS: 1335011-98-7
• 化学式: C₁₉H₁₉NO₂
• 分子量: 293.365
• InChiKey: HUOOGLOSOSLEPY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  42.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-hydroxy-1-(3-methylbut-2-en-1-yl)-9H-carbazole-3-carbaldehyde 、 碘甲烷 在 sodium hydride 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 0.17h， 以15%的产率得到2-methoxy-1-(3-methylbuten-1-yl)-9H-carbazole-3-carbaldehyde
  参考文献：
  名称：

  Synthesis and cytotoxic activity of the heptaphylline and 7-methoxyheptaphylline series

  摘要：

  Nineteen carbazole alkaloids modified from heptaphylline (I) and 7-methoxyheptaphylline (II) isolated from Clausena harmandiana were synthesized. Among these derivatives, Ih and IIi showed cytotoxicity against the NCI-H187 cell line with IC50 values of 0.02 and 0.66 mu M, respectively, which are about 138 and 4 fold stronger than the ellipticine standard. In addition, oxime Ih displayed cytotoxicity against KB cells with an IC50 value of 0.17 mu M which is about 10 times stronger than the ellipticine. This compound demonstrated weak cytotoxicity against Vero cells (IC50 = 66.01 mu M). The results show convincingly that Ih may be a promising lead for the development of cytotoxic agents. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.05.041

文献信息

• Synthesis and cytotoxic activity of the heptaphylline and 7-methoxyheptaphylline series
  作者：Tula Thongthoom、Pawantree Promsuwan、Chavi Yenjai

  DOI：10.1016/j.ejmech.2011.05.041

  日期：2011.9

  Nineteen carbazole alkaloids modified from heptaphylline (I) and 7-methoxyheptaphylline (II) isolated from Clausena harmandiana were synthesized. Among these derivatives, Ih and IIi showed cytotoxicity against the NCI-H187 cell line with IC50 values of 0.02 and 0.66 mu M, respectively, which are about 138 and 4 fold stronger than the ellipticine standard. In addition, oxime Ih displayed cytotoxicity against KB cells with an IC50 value of 0.17 mu M which is about 10 times stronger than the ellipticine. This compound demonstrated weak cytotoxicity against Vero cells (IC50 = 66.01 mu M). The results show convincingly that Ih may be a promising lead for the development of cytotoxic agents. (C) 2011 Elsevier Masson SAS. All rights reserved.