5-chloro-2-(3-(dimethylamino)propyl)indazolo[3,4-fg]isoquinolin-6(2H)-one | 1011477-49-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡唑类
• 英文名称: 5-chloro-2-(3-(dimethylamino)propyl)indazolo[3,4-fg]isoquinolin-6(2H)-one
• 英文别名: 10-Chloro-14-[3-(dimethylamino)propyl]-5,14,15-triazatetracyclo[7.6.1.02,7.013,16]hexadeca-1(15),2(7),3,5,9,11,13(16)-heptaen-8-one
• CAS: 1011477-49-8
• 化学式: C₁₈H₁₇ClN₄O
• 分子量: 340.812
• InChiKey: XJWQMNCKFJWMMJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  51
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-chloro-2-(3-(dimethylamino)propyl)indazolo[3,4-fg]isoquinolin-6(2H)-one 、 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20%的产率得到14-[3-(Dimethylamino)propyl]-10-[3-[3-[[14-[3-(dimethylamino)propyl]-8-oxo-5,14,15-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]-5,14,15-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：

  3-(dimethylamino)propylhydrazine 、 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66%的产率得到5-chloro-2-(3-(dimethylamino)propyl)indazolo[3,4-fg]isoquinolin-6(2H)-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

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