Abstract

An unexpected efficient basic catalyzed heterocyclization reactions were carried out to build blocks of potentially bioactive 2-{pyrano[2,3-c]pyrazoles-4-ylidene}malononitrile skeleton fused with pyrazole, pyridine, pyrimidine, diazepine, chromone, pyrano[2,3-c]pyrazole, and pyrano[2,3-d]pyrimidine systems in novel molecular frames. The method depended on treatment of 6-amino-4-(4-oxo-4H-chromen-3-yl)-3-phenyl-1,4-dihydro-pyrano[2,3-c]pyrazole-5-carbonitrile (1) with different nitrogen and carbon nucleophiles in ethanolic sodium ethoxide. Possible mechanisms for the reactions were suggested. Elemental analyses and spectral techniques confirmed the structures of the isolated products. The compounds were evaluated for cytotoxic activities. Among the synthesized compounds, both 4 and 11 exhibited the most potent cytotoxicity against all used cancer cell lines.

摘要

进行了意想不到的高效碱性催化杂环化反应，以构建与吡唑、吡啶、嘧啶、二氮杂卓、色酮、吡喃稠合的具有潜在生物活性的 2-{pyrano[2,3 - c ]pyrazoles-4-ylidene}丙二腈骨架块[2 ,3 - c ]吡唑和吡喃并[2,3- d ]嘧啶系统在新的分子框架中。该方法依赖于处理 6-amino-4-(4-oxo-4 H -chromen-3-yl)-3-phenyl-1,4-dihydro-pyrano[2,3- c ]pyrazole-5-carbonitrile ( 1) 在乙醇乙醇钠中具有不同的氮和碳亲核试剂。提出了可能的反应机制。元素分析和光谱技术证实了分离产物的结构。评估了这些化合物的细胞毒活性。在合成的化合物中，4和11对所有使用的癌细胞系都表现出最有效的细胞毒性。