3-(furan-2-yl)-6,7-dihydro-2H-indazol-4(5H)-one | 13789-48-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(furan-2-yl)-6,7-dihydro-2H-indazol-4(5H)-one
• 英文别名: 4-Oxo-3--4,5,6,7-tetrahydro-2H-indazol；3-furan-2-yl-1(2),5,6,7-tetrahydro-indazol-4-one
• CAS: 13789-48-5
• 化学式: C₁₁H₁₀N₂O₂
• 分子量: 202.213
• InChiKey: RTONEKPXMYPGFI-UHFFFAOYSA-N

反应信息

• 作为产物：
  描述：

  1,3-环己二酮 在 哌啶 、 溶剂黄146 作用下， 以 二甲基亚砜 为溶剂， 生成 3-(furan-2-yl)-6,7-dihydro-2H-indazol-4(5H)-one
  参考文献：
  名称：

  Teuber,H.-J.; Braun,R., Chemische Berichte, 1967, vol. 100, # 4, p. 1353 - 1366

  摘要：

  DOI：

文献信息

• Multi-component synthesis of pyrazolo[1,5-a]quinazoline, thiazole and thiophene derivatives as cytotoxic agents
  作者：Rafat M. Mohareb、Maher H. E. Helal、Amany E. Mayhoub、Amira E. M. Abdallah

  DOI：10.4314/bcse.v37i6.17

  日期：——

  ABSTRACT. This study demonstrated the synthesis of a number of pyrazolo[1,5-a]quinazoline derivatives about 24 products based on the starting material 4-(2-phenylhydrazono)-4H-pyrazol-3-amine derivatives 1a-f. Moreover, other ring systems including thiophene, pyrazole, thiazole and pyran (16 compounds) were prepared based on another starting compounds 2-(furan-2-ylmethylene)cyclohexane-1,3-dione 10  and 5,5-dimethyl-3-phenyl-2-thioxo-2,3,5,6-tetrahydrobenzo[d]thiazol-7(4H)-one 18. The multi-component reaction was used to prepare all the previous compounds. The structures of all the synthesised compounds were confirmed by the analytical and spectral data. Some selected compounds were chosen to test their anticancer activity against six cancer cell lines, namely A549, HT-29, MKN-45, U87MG, SMMC-7721 and, H460 utilizing foretinib as the positive control and the standard MTT assay in vitro. Toward the tested cell lines, nine compounds were the most cytotoxic compounds. The results obtained revealed that the synthesized compounds are good cytotoxic agents and of great impact for future work. KEY WORDS: Multi-component reactions, Pyrazolo[1,5-a]quinazoline, Thiophene, Thiazole, Cytotoxicity Bull. Chem. Soc. Ethiop. 2023, 37(6), 1521-1538. DOI: https://dx.doi.org/10.4314/bcse.v37i6.17

  摘要本研究以起始化合物 4-(2-苯肼基)-4H-吡唑-3-胺衍生物 1a-f 为基础，合成了一系列吡唑并[1,5-a]喹唑啉衍生物，约 24 个产物。此外，以另一种起始化合物 2-(呋喃-2-亚甲基)环己烷-1,3-二酮 10 和 5,5-二甲基-3-苯基-2-硫酮-2,3,5,6-四氢苯并[d]噻唑-7(4H)-酮 18 为基础，制备了包括噻吩、吡唑、噻唑和吡喃在内的其他环系统（16 个化合物）。多组分反应用于制备之前的所有化合物。分析和光谱数据证实了所有合成化合物的结构。利用 foretinib 作为阳性对照和体外标准 MTT 试验，选择了一些化合物来测试它们对六种癌细胞株（即 A549、HT-29、MKN-45、U87MG、SMMC-7721 和 H460）的抗癌活性。在测试的细胞系中，有九种化合物的细胞毒性最强。研究结果表明，合成的化合物具有良好的细胞毒性，对今后的工作具有重要影响； 关键词：多组分反应 吡唑并[1,5-a]喹唑啉 噻吩 噻唑 细胞毒性 ； Bull.Chem.Soc. Ethiop.2023, 37(6), 1521-1538.DOI: hTTps://dx.doi.org/10.4314/bcse.v37i6.17