2-[6-(dimethylamino)-1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl]ethyl 2-[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]acetate | 1246182-31-9

• 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: 2-[6-(dimethylamino)-1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl]ethyl 2-[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]acetate
• 英文别名: 2-[6-(dimethylamino)-1,3-dioxobenzo[de]isoquinolin-2-yl]ethyl 2-[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetate
• CAS: 1246182-31-9
• 化学式: C₃₅H₃₀ClN₃O₆
• 分子量: 624.093
• InChiKey: SGHZYSUNTQMMST-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  45
• 可旋转键数：
  9
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  98.2
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  英文名称 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 乙醇 、 氯仿 为溶剂， 反应 49.5h， 生成 2-[6-(dimethylamino)-1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl]ethyl 2-[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]acetate
  参考文献：
  名称：

  Novel naphthalimide–indomethacin hybrids as potential antitumor agents: effects of linkers on hypoxic/oxic cytotoxicity and apoptosis-inducing activity

  摘要：

  A series of novel naphthalimide-indomethacin hybrids with different linkers were designed and synthesized. Their antitumor activity was evaluated against HeLa, A549, P388, HL-60, MCF-7, HCT-8, and A375 cancer cell lines in vitro. Preliminary results showed that the hybrids had moderate cytotoxic activity with 50% inhibition concentration (IC50) values of similar to 10(-5) M, and could effectively induce apoptosis in HeLa cells. More importantly, the amide derivatives had better cytotoxic and proapoptotic activity than their ester counterparts, whereas the ester derivatives had hypoxic preferred cytotoxicity and might be used as promising candidates of prodrug in hypoxic tumor cells. This work provides a novel class of naphthalimide-indomethacin hybrids with unique antitumor activity for further optimization.

  DOI：

  10.1007/s00706-010-0337-x

文献信息

• Novel naphthalimide–indomethacin hybrids as potential antitumor agents: effects of linkers on hypoxic/oxic cytotoxicity and apoptosis-inducing activity
  作者：Aibin Wu、Yufang Xu、Xuhong Qian

  DOI：10.1007/s00706-010-0337-x

  日期：2010.8

  A series of novel naphthalimide-indomethacin hybrids with different linkers were designed and synthesized. Their antitumor activity was evaluated against HeLa, A549, P388, HL-60, MCF-7, HCT-8, and A375 cancer cell lines in vitro. Preliminary results showed that the hybrids had moderate cytotoxic activity with 50% inhibition concentration (IC50) values of similar to 10(-5) M, and could effectively induce apoptosis in HeLa cells. More importantly, the amide derivatives had better cytotoxic and proapoptotic activity than their ester counterparts, whereas the ester derivatives had hypoxic preferred cytotoxicity and might be used as promising candidates of prodrug in hypoxic tumor cells. This work provides a novel class of naphthalimide-indomethacin hybrids with unique antitumor activity for further optimization.