9-benzyl-1-methyl-2-(2-(naphthalen-2-yl)-2-oxoethyl)-9H-pyrido[3,4-b]indol-2-ium bromide

• 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: 9-benzyl-1-methyl-2-(2-(naphthalen-2-yl)-2-oxoethyl)-9H-pyrido[3,4-b]indol-2-ium bromide
• 英文别名: 2-(9-Benzyl-1-methylpyrido[3,4-b]indol-2-ium-2-yl)-1-naphthalen-2-ylethanone;bromide；2-(9-benzyl-1-methylpyrido[3,4-b]indol-2-ium-2-yl)-1-naphthalen-2-ylethanone;bromide
• 化学式: Br*C₃₁H₂₅N₂O
• 分子量: 521.456
• InChiKey: SRTZBUGHWZCYGJ-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  3.48
• 重原子数：
  35
• 可旋转键数：
  5
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  25.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-methyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid 在 碘苯二乙酸 、 sodium hydride 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 13.0h， 生成 9-benzyl-1-methyl-2-(2-(naphthalen-2-yl)-2-oxoethyl)-9H-pyrido[3,4-b]indol-2-ium bromide
  参考文献：
  名称：

  Design, synthesis and in vitro cytotoxicity studies of novel β -carbolinium bromides

  摘要：

  A series of novel beta-carbolinium bromides has been synthesized from easily accessible beta-carbolines and 1-aryl-2-bromoethanones. The newly synthesized compounds were evaluated for their in vitro anticancer activity. Among the synthesized derivatives, compounds 161, 16o and 16s exhibited potent anticancer activity with IC50 values of <10 mu M against tested cancer cell lines. The most potent analogue 161 was broadly active against all the tested cancer cell lines (IC50 = 3.16-7.93 mu M). In order to test the mechanism of cell death, we exposed castration resistant prostate cancer cell line (C4-2) to compounds 161 and 16s, which resulted in increased levels of cleaved PARP1 and AO/EB staining, indicating that a-carbolinium salts induce apoptosis in these cells. Additionally, the most potent beta-carbolines 161 and 16s were found to inhibit tubulin polymerization. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2017.02.010