2-(2-(diethylamino)ethyl)-6-oxo-2,6-dihydroindazolo[4,3-gh]isoquinolin-5-yl 4-methylbenzenesulfonate | 1011477-46-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 2-(2-(diethylamino)ethyl)-6-oxo-2,6-dihydroindazolo[4,3-gh]isoquinolin-5-yl 4-methylbenzenesulfonate
• 英文别名: 2-[2-(diethylamino)ethyl]-5-(p-toluenesulfonyloxy)iso-quino[8,7,6-cd]indazole-6(2H)-one；[14-[2-(Diethylamino)ethyl]-8-oxo-4,14,15-triazatetracyclo[7.6.1.02,7.013,16]hexadeca-1(15),2(7),3,5,9,11,13(16)-heptaen-10-yl] 4-methylbenzenesulfonate
• CAS: 1011477-46-5
• 化学式: C₂₆H₂₆N₄O₄S
• 分子量: 490.583
• InChiKey: VFWIVMGWFAZRGZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  35
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  103
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-(2-(diethylamino)ethyl)-6-oxo-2,6-dihydroindazolo[4,3-gh]isoquinolin-5-yl 4-methylbenzenesulfonate 、 N,N-双(3-氨丙基)甲胺 在 三乙胺 作用下， 以 乙二醇乙醚 为溶剂， 反应 5.0h， 以30%的产率得到14-[2-(Diethylamino)ethyl]-10-[3-[3-[[14-[2-(diethylamino)ethyl]-8-oxo-4,14,15-triazatetracyclo[7.6.1.02,7.013,16]hexadeca-1(15),2(7),3,5,9,11,13(16)-heptaen-10-yl]amino]propyl-methylamino]propylamino]-4,14,15-triazatetracyclo[7.6.1.02,7.013,16]hexadeca-1(15),2(7),3,5,9,11,13(16)-heptaen-8-one
  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-[2-(diethylamino)ethyl]hydrazine 、 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 1.0h， 以45%的产率得到2-(2-(diethylamino)ethyl)-6-oxo-2,6-dihydroindazolo[4,3-gh]isoquinolin-5-yl 4-methylbenzenesulfonate
  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

• 2-AMINOALKYL-5-AMINOALKYLAMINO SUBSTITUTED ISOQUINOINDAZOLE-6-(2H)-ONES WITH ANTITUMOUR ACTIVITY
  申请人：THE UNIVERSITY OF VERMONT

  公开号：EP0662076B1

  公开（公告）日：2001-04-11
• HETERO-ANNULATED INDAZOLES
  申请人：Novuspharma S.p.A.

  公开号：EP0750619B1

  公开（公告）日：2001-05-30
• US5519029A
  申请人：——

  公开号：US5519029A

  公开（公告）日：1996-05-21
• US5596097A
  申请人：——

  公开号：US5596097A

  公开（公告）日：1997-01-21
• US5604246A
  申请人：——

  公开号：US5604246A

  公开（公告）日：1997-02-18