1-methyl-1,4-dihydro-1H-indeno[1,2-c]pyrazole-3-carboxylic acid | 665020-23-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-methyl-1,4-dihydro-1H-indeno[1,2-c]pyrazole-3-carboxylic acid
• 英文别名: 1-methyl-1,4-dihydroindeno[1,2-c]pyrazole-3-carboxylic acid；1-methyl-4H-indeno[1,2-c]pyrazole-3-carboxylic acid
• CAS: 665020-23-5
• 化学式: C₁₂H₁₀N₂O₂
• 分子量: 214.224
• InChiKey: AMBYXLSFMUTOQU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  55.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-methyl-1,4-dihydro-1H-indeno[1,2-c]pyrazole-3-carboxylic acid 在 氯化亚砜 、 三乙胺 作用下， 以 四氯化碳 、 乙腈 为溶剂， 反应 2.0h， 生成 (1,5-dimethyl-9-oxo-3,7-diazabicyclo[3.3.1]nonane-3,7-diyl)bis((1-methyl-1,4-dihydroindeno[1,2-c]pyrazol-3-yl)methanone)
  参考文献：
  名称：

  Design and Evaluation of Bispidine-Based SARS-CoV-2 Main Protease Inhibitors

  摘要：

  DOI：

  10.1021/acsmedchemlett.1c00299
• 作为产物：
  描述：

  ethyl β-(1-oxo-2,3-dihydro-1H-inden-2-yl)-α-oxoacetate 在 氢氧化钾 作用下， 以 甲醇 、 乙醇 为溶剂， 生成 1-methyl-1,4-dihydro-1H-indeno[1,2-c]pyrazole-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

• 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.
• Design and Evaluation of Bispidine-Based SARS-CoV-2 Main Protease Inhibitors
  作者：Dmitriy Shcherbakov、Dmitriy Baev、Mikhail Kalinin、Alexander Dalinger、Varvara Chirkova、Svetlana Belenkaya、Aleksei Khvostov、Dmitry Krut’ko、Aleksei Medved’ko、Ekaterina Volosnikova、Elena Sharlaeva、Daniil Shanshin、Tatyana Tolstikova、Olga Yarovaya、Rinat Maksyutov、Nariman Salakhutdinov、Sergey Vatsadze

  DOI：10.1021/acsmedchemlett.1c00299

  日期：2022.1.13