ethyl 1-methyl-1,4-dihydro-indeno[1,2-c]pyrazole-3-carboxylate | 665020-28-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: ethyl 1-methyl-1,4-dihydro-indeno[1,2-c]pyrazole-3-carboxylate
• CAS: 665020-28-0
• 化学式: C₁₄H₁₄N₂O₂
• 分子量: 242.277
• InChiKey: IWZOOQUEUGHRCQ-UHFFFAOYSA-N

物化性质

• 沸点：
  419.0±33.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.17
• 重原子数：
  18.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  44.12
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  ethyl 1-methyl-1,4-dihydro-indeno[1,2-c]pyrazole-3-carboxylate 在 氯化亚砜 、 三乙胺 、 sodium hydroxide 作用下， 以 四氯化碳 、 水 、 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：

  1-茚酮 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 生成 ethyl 1-methyl-1,4-dihydro-indeno[1,2-c]pyrazole-3-carboxylate
  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

• Synthesis and Antineoplastic Evaluation of Novel Unsymmetrical 1,3,4-Oxadiazoles
  作者：Valentina Nieddu、Giansalvo Pinna、Irene Marchesi、Luca Sanna、Battistina Asproni、Gerard A. Pinna、Luigi Bagella、Gabriele Murineddu

  DOI：10.1021/acs.jmedchem.6b00468

  日期：2016.12.8

  A series of novel 1,3,4-oxadiazoles was synthesized and evaluated for their cytotoxic activity in in vitro tumor models. Four of the new compounds (2d, 2j, 2k, and 2n) showed growth inhibition in the XTT dye assay. The most active agent, 2j, showed high potency against human cancer cells with IC50s ranging from 0.05 to 1.7 μM. Preliminary SAR correlations suggested that the nature of chains on the

  合成了一系列新型的1,3,4-恶二唑类化合物，并在体外肿瘤模型中评估了它们的细胞毒活性。在XTT染料分析中，四种新化合物（2d，2j，2k和2n）显示出生长抑制作用。活性最高的试剂2j对人癌细胞显示出高效力，IC 50值为0.05至1.7μM。初步的SAR相关性表明，恶二唑上链的性质对于体外抗肿瘤效力很重要。化合物2j确定了细胞周期的G 2 / M停滞，并且还激活了强烈的凋亡反应。β-微管蛋白免疫荧光分析表明该化合物2j有效抑制所有癌细胞系中的微管组织，导致异常纺锤体的形成，这并不影响正常人成纤维细胞NB1，Mrc-5和IBR3。由于所有这些原因，化合物2j在化学预防或化学治疗策略中可能是很好的候选者。