1,9-bis(9-chloro-5,10-dioxo-5,10-dihydrobenzo[g]isoquinoline-6-yl)-5-methyl-1,5,9-triazanonane | 1011477-48-7

• 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-chloro-5,10-dioxo-5,10-dihydrobenzo[g]isoquinoline-6-yl)-5-methyl-1,5,9-triazanonane
• 英文别名: 9-Chloro-6-[3-[3-[(9-chloro-5,10-dioxobenzo[g]isoquinolin-6-yl)amino]propyl-methylamino]propylamino]benzo[g]isoquinoline-5,10-dione
• CAS: 1011477-48-7
• 化学式: C₃₃H₂₇Cl₂N₅O₄
• 分子量: 628.514
• InChiKey: VRYGTVKWQLKIHQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  44
• 可旋转键数：
  10
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  121
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  1,9-bis(9-chloro-5,10-dioxo-5,10-dihydrobenzo[g]isoquinoline-6-yl)-5-methyl-1,5,9-triazanonane 、 N,N-二甲基-1,3-二氨基丙烷 反应 2.0h， 以61%的产率得到9-[3-(Dimethylamino)propylamino]-6-[3-[3-[[9-[3-(dimethylamino)propylamino]-5,10-dioxobenzo[g]isoquinolin-6-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 、 1-fluorobenz[g]isoquinoline-5,10-dione derivative 在 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 以28%的产率得到1,9-bis(9-chloro-5,10-dioxo-5,10-dihydrobenzo[g]isoquinoline-6-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.