1H-benzo[g]indazole-3-carboxylic acid | 665020-19-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1H-benzo[g]indazole-3-carboxylic acid
• 英文别名: 2H-benzo[g]indazole-3-carboxylic acid
• CAS: 665020-19-9
• 化学式: C₁₂H₈N₂O₂
• 分子量: 212.208
• InChiKey: DQANFGSPWDQZSA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  66
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1H-benzo[g]indazole-3-carboxylic acid 以 N,N-二甲基甲酰胺 为溶剂， 反应 51.0h， 生成 N3-{2-[{2-[(1H-benzo[g]indazole-3-yl-carbonyl)amino]ethyl}(methyl)amino]ethyl}-1H-benzo[g]indazole-3-carboxamide
  参考文献：
  名称：

  Chromophore-modified bis-benzo[g]indole carboxamides: synthesis and antiproliferative activity of bis-benzo[g]indazole-3-carboxamides and related dimers

  摘要：

  Tricyclic pyrazole dimers that comprise two kinds of CONH-(CH(2))(n)-N(CH(3))-(CH(2))(n)-NHCO bridges to which are linked potential DNA-intercalating groups such as 1H-benzo[g]indazole, 2H-benzo[g]indazole and 1,4-dihydroindeno[1,2-c]pyrazole were designed, synthesized and some of them evaluated in vitro by NCI (Bethesda, USA) against nine types of cancer cells. Compounds 2a, 2f-i and 2o-r demonstrated significant antiproliferative activity, all with GI(50) values in the low micromolar range. Preliminary analysis of the structure-activity relationship for dimers 2 indicated that: (i) in the ground terms (2a and 2k) antitumor activities were strongly related to the type of chromophore, (ii) in contrast, either 1H-benzo[g]indazole- or 1,4-dihydroindeno[1,2-c]pyrazole-dimers when bore a N(1)-aryl group (2g, 2h, 2i, 2o, 2p, 2q and 2r) generally showed a good level of antitumor potency and (iii) for the most representative compounds (pairs of compounds: 2g,2h; 2o,2p and 2q,2r) the length of the bridges did not significantly contribute to the variations in cytotoxicity. Two members of this series, 2f and 2q, were selected and tested in the hollow fiber cell assay to evaluate in a preliminary fashion their in vivo antitumor activity. Finally, viscosity measurement of 2f with poly(dA-dT)(2), confirmed that these promising compounds behaved as typical DNA-intercalating agents.

  DOI：

  10.1016/s0014-827x(03)00131-9
• 作为产物：
  描述：

  ethyl 4,5-dihydro-1H-benzo[g]indazole-3-carboxylate 在 氢氧化钾 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 12.0h， 生成 1H-benzo[g]indazole-3-carboxylic acid
  参考文献：
  名称：

  Chromophore-modified bis-benzo[g]indole carboxamides: synthesis and antiproliferative activity of bis-benzo[g]indazole-3-carboxamides and related dimers

  摘要：

  Tricyclic pyrazole dimers that comprise two kinds of CONH-(CH(2))(n)-N(CH(3))-(CH(2))(n)-NHCO bridges to which are linked potential DNA-intercalating groups such as 1H-benzo[g]indazole, 2H-benzo[g]indazole and 1,4-dihydroindeno[1,2-c]pyrazole were designed, synthesized and some of them evaluated in vitro by NCI (Bethesda, USA) against nine types of cancer cells. Compounds 2a, 2f-i and 2o-r demonstrated significant antiproliferative activity, all with GI(50) values in the low micromolar range. Preliminary analysis of the structure-activity relationship for dimers 2 indicated that: (i) in the ground terms (2a and 2k) antitumor activities were strongly related to the type of chromophore, (ii) in contrast, either 1H-benzo[g]indazole- or 1,4-dihydroindeno[1,2-c]pyrazole-dimers when bore a N(1)-aryl group (2g, 2h, 2i, 2o, 2p, 2q and 2r) generally showed a good level of antitumor potency and (iii) for the most representative compounds (pairs of compounds: 2g,2h; 2o,2p and 2q,2r) the length of the bridges did not significantly contribute to the variations in cytotoxicity. Two members of this series, 2f and 2q, were selected and tested in the hollow fiber cell assay to evaluate in a preliminary fashion their in vivo antitumor activity. Finally, viscosity measurement of 2f with poly(dA-dT)(2), confirmed that these promising compounds behaved as typical DNA-intercalating agents.

  DOI：

  10.1016/s0014-827x(03)00131-9

文献信息

• SUBSTITUTED PYRAZOLYL BENZENESULFAMIDE COMPOUNDS FOR THE TREATMENT OF INFLAMMATION
  申请人：Pharmacia Corporation

  公开号：EP1438293A2

  公开（公告）日：2004-07-21
• ENDOTHELIN RECEPTOR ANTAGONISTS FOR EARLY STAGE IDIOPATHIC PULMONARY FIBROSIS
  申请人：Clozel Martine

  公开号：US20100022568A1

  公开（公告）日：2010-01-28

  This present invention relates to the use of an endothelin receptor antagonist for the preparation of a medicament for the treatment of early stage idiopathic pulmonary fibrosis.
• [EN] SUBSTITUTED PYRAZOLYL BENZENESULFAMIDE COMPOUNDS FOR THE TREATMENT OF INFLAMMATION<br/>[FR] COMPOSES SUBSTITUES DE SULFAMIDE BENZENE DE PYRAZOLYL DESTINES AU TRAITEMENT DES INFLAMMATIONS
  申请人：PHARMACIA CORP

  公开号：WO2003027075A2

  公开（公告）日：2003-04-03

  The present invention relates to substituted pyrazolyl derivatives, compositions comprising such, intermediates, methods of making substituted pyrazolyl derivatives, and methods for treating cancer, inflammation, and inflammation-associated disorders, such as arthritis.
• Chromophore-modified bis-benzo[g]indole carboxamides: synthesis and antiproliferative activity of bis-benzo[g]indazole-3-carboxamides and related dimers
  作者：Gérard A Pinna、Maria A Pirisi、Jean-Mario Mussinu、Gabriele Murineddu、Giovanni Loriga、Amedeo Pau、Giuseppe E Grella

  DOI：10.1016/s0014-827x(03)00131-9

  日期：2003.9

  Tricyclic pyrazole dimers that comprise two kinds of CONH-(CH(2))(n)-N(CH(3))-(CH(2))(n)-NHCO bridges to which are linked potential DNA-intercalating groups such as 1H-benzo[g]indazole, 2H-benzo[g]indazole and 1,4-dihydroindeno[1,2-c]pyrazole were designed, synthesized and some of them evaluated in vitro by NCI (Bethesda, USA) against nine types of cancer cells. Compounds 2a, 2f-i and 2o-r demonstrated significant antiproliferative activity, all with GI(50) values in the low micromolar range. Preliminary analysis of the structure-activity relationship for dimers 2 indicated that: (i) in the ground terms (2a and 2k) antitumor activities were strongly related to the type of chromophore, (ii) in contrast, either 1H-benzo[g]indazole- or 1,4-dihydroindeno[1,2-c]pyrazole-dimers when bore a N(1)-aryl group (2g, 2h, 2i, 2o, 2p, 2q and 2r) generally showed a good level of antitumor potency and (iii) for the most representative compounds (pairs of compounds: 2g,2h; 2o,2p and 2q,2r) the length of the bridges did not significantly contribute to the variations in cytotoxicity. Two members of this series, 2f and 2q, were selected and tested in the hollow fiber cell assay to evaluate in a preliminary fashion their in vivo antitumor activity. Finally, viscosity measurement of 2f with poly(dA-dT)(2), confirmed that these promising compounds behaved as typical DNA-intercalating agents.