1,9-bis{9-[(5,10-dioxo-5,10-dihydrobenzo[g]isoquinoline-6-yl)tosylate]yl}-5-methyl-1,5,9-triazanonane | 1011477-45-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 1,9-bis{9-[(5,10-dioxo-5,10-dihydrobenzo[g]isoquinoline-6-yl)tosylate]yl}-5-methyl-1,5,9-triazanonane
• 英文别名: [9-[3-[Methyl-[3-[[6-(4-methylphenyl)sulfonyloxy-5,10-dioxobenzo[g]isoquinolin-9-yl]amino]propyl]amino]propylamino]-5,10-dioxobenzo[g]isoquinolin-6-yl] 4-methylbenzenesulfonate
• CAS: 1011477-45-4
• 化学式: C₄₇H₄₁N₅O₁₀S₂
• 分子量: 900.002
• InChiKey: FEZQOVVRXIZQPP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.1
• 重原子数：
  64
• 可旋转键数：
  16
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  225
• 氢给体数：
  2
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  1,9-bis{9-[(5,10-dioxo-5,10-dihydrobenzo[g]isoquinoline-6-yl)tosylate]yl}-5-methyl-1,5,9-triazanonane 、 N,N-二乙基乙二胺 反应 2.0h， 以60%的产率得到6-[2-(Diethylamino)ethylamino]-9-[3-[3-[[6-[2-(diethylamino)ethylamino]-5,10-dioxobenzo[g]isoquinolin-9-yl]amino]propyl-methylamino]propylamino]benzo[g]isoquinoline-5,10-dione
  参考文献：
  名称：

  Synthesis and Antitumor Evaluation of Bis Aza-anthracene-9,10-diones and Bis Aza-anthrapyrazole-6-ones

  摘要：

  The good results obtained as potential antitumor drugs with aza-anthracenediones and aza-anthrapyrazoles, e.g. pixantrone, 1a, and 1b (Chart 1), prompted us to design and synthesize a series of symmetrical bis derivatives, compounds 7-10 (Chart 1). These compounds are dimers of different aza-anthracenedione and aza-anthrapyrazolone monomers connected by the linker found to be the most appropriate among potential bis intercalators synthesized by us. The DNA-binding properties of bis derivatives 7 and 8 have been examined using fluorometric techniques: these target compounds are excellent DNA ligands, with a clear binding site preference for AT-rich duplexes. In vitro cytotoxic activity of all target compounds 7-10 and of reference compound pixantrone toward human cancer adenocarcinoma cell line HT29 is also described. Two selected compounds have been investigated for their capacity of inducing early apoptosis.

  DOI：

  10.1021/jm7013937
• 作为产物：
  描述：

  N,N-双(3-氨丙基)甲胺 、 9-fluoro-6-<<(4-methylphenyl)sulfonyl>oxy>benzisoquinoline-5,10-dione 在 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以25%的产率得到1,9-bis{9-[(5,10-dioxo-5,10-dihydrobenzo[g]isoquinoline-6-yl)tosylate]yl}-5-methyl-1,5,9-triazanonane
  参考文献：
  名称：

  Synthesis and Antitumor Evaluation of Bis Aza-anthracene-9,10-diones and Bis Aza-anthrapyrazole-6-ones

  摘要：

  The good results obtained as potential antitumor drugs with aza-anthracenediones and aza-anthrapyrazoles, e.g. pixantrone, 1a, and 1b (Chart 1), prompted us to design and synthesize a series of symmetrical bis derivatives, compounds 7-10 (Chart 1). These compounds are dimers of different aza-anthracenedione and aza-anthrapyrazolone monomers connected by the linker found to be the most appropriate among potential bis intercalators synthesized by us. The DNA-binding properties of bis derivatives 7 and 8 have been examined using fluorometric techniques: these target compounds are excellent DNA ligands, with a clear binding site preference for AT-rich duplexes. In vitro cytotoxic activity of all target compounds 7-10 and of reference compound pixantrone toward human cancer adenocarcinoma cell line HT29 is also described. Two selected compounds have been investigated for their capacity of inducing early apoptosis.

  DOI：

  10.1021/jm7013937

文献信息

• Synthesis and Antitumor Evaluation of Bis Aza-anthracene-9,10-diones and Bis Aza-anthrapyrazole-6-ones
  作者：Ippolito Antonini、Giorgio Santoni、Roberta Lucciarini、Consuelo Amantini、Diego Dal Ben、Rosaria Volpini、Gloria Cristalli

  DOI：10.1021/jm7013937

  日期：2008.2.1

  The good results obtained as potential antitumor drugs with aza-anthracenediones and aza-anthrapyrazoles, e.g. pixantrone, 1a, and 1b (Chart 1), prompted us to design and synthesize a series of symmetrical bis derivatives, compounds 7-10 (Chart 1). These compounds are dimers of different aza-anthracenedione and aza-anthrapyrazolone monomers connected by the linker found to be the most appropriate among potential bis intercalators synthesized by us. The DNA-binding properties of bis derivatives 7 and 8 have been examined using fluorometric techniques: these target compounds are excellent DNA ligands, with a clear binding site preference for AT-rich duplexes. In vitro cytotoxic activity of all target compounds 7-10 and of reference compound pixantrone toward human cancer adenocarcinoma cell line HT29 is also described. Two selected compounds have been investigated for their capacity of inducing early apoptosis.