6-fluoro-9-(p-toluenesulfonyloxy)benzo[g]isoquinoline-5,10-dione | 172779-12-3

• 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: 6-fluoro-9-(p-toluenesulfonyloxy)benzo[g]isoquinoline-5,10-dione
• 英文别名: 6-Fluoro-9-(p-toluenesulfonyloxy)benzo[g]isoquinolin-5,10-dion；6-Fluoro-9-(p-toluenesulfonyloxy)benzo [g]isoquinoline-5,10-dione；(6-fluoro-5,10-dioxobenzo[g]isoquinolin-9-yl) 4-methylbenzenesulfonate
• CAS: 172779-12-3
• 化学式: C₂₀H₁₂FNO₅S
• 分子量: 397.383
• InChiKey: PUSLJPRNTQZMPH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  98.8
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  6-fluoro-9-(p-toluenesulfonyloxy)benzo[g]isoquinoline-5,10-dione 、 2-肼基-N,N-二甲基-乙胺 在 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 生成 2-[2-(Dimethylamino)ethyl]-5-(p-toluenesulfonyloxy)isoquino[5,6,7-cd]indazol-6(2H)-on
  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

• Hetero-annulated indazoles
  申请人：The University of Vermont

  公开号：US05596097A1

  公开（公告）日：1997-01-21

  This invention is directed to heteroannulated indazoles namely to 2,5-disubstituted quinolino-, isoquinolino-, phthalazino-, and quinoxalino- annulated indazole-6(2H)-ones and related mono N-oxides. These compounds have been shown to have antitumor activity.

  本发明涉及杂环脱氢吲唑，即2,5-二取代的喹啉、异喹啉、邻苯二氮杂茂和喹啉并脱氢吲唑-6(2H)-酮及其相关的单个N-氧化物。这些化合物已被证明具有抗肿瘤活性。
• HETERO-ANNULATED INDAZOLES
  申请人：Novuspharma S.p.A.

  公开号：EP0750619B1

  公开（公告）日：2001-05-30
• US5596097A
  申请人：——

  公开号：US5596097A

  公开（公告）日：1997-01-21
• [EN] HETERO-ANNULATED INDAZOLES<br/>[FR] INDAZOLES HETERO-ANNELES
  申请人：BOEHRINGER MANNHEIM ITALIA, S.P.A.

  公开号：WO1995024407A1

  公开（公告）日：1995-09-14

  (EN) This invention is directed to hetero-annulated indazoles of formula (I) and namely to 2,5-disubstituted quinolino-, isoquinolino-, phthalazino-, and quinoxalino-annulated indazole-6(2H)-ones and related mono N-oxides. These compounds have been shown to have antitumor activity.(FR) L'invention concerne des indazoles hétéro-annelés de Formule (I), à savoir des indaxole-6(2H)-ones quinolino-, isoquinolino-, phtalazino- et quinoxalino 2,5- disubstitués et leurs mono N-oxydes apparentés. On a démontré que ces composés présentent une activité antitumorale.
• 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.