Chemistry Department, Faculty of Sciences, University of Sharjah, Sharjah 27272, UAE.
Chemistry of Natural and Microbial Products Department, Pharmaceutical and Drug Industries Research Division, National Research Centre, Dokki, Cairo 12622, Egypt.
Molecules. 2020 Feb 5;25(3):672. doi: 10.3390/molecules25030672.
This work describes the utility of pyrazole-4-carbaldehyde as starting material for the synthesis of a novel potent series of 5α-reductase and aromatase inhibitors derived from 1,2,3-triazole derivative. Condensation of with active methylene and different amino pyrazoles produced the respective Schiff bases -, and . On the other hand, was reacted with ethyl cyanoacetate and thiourea in one-pot reaction to afford the pyrazolo-6- thioxopyridin-2-[3]-one (). Moreover, α-β unsaturated chalcone derivative was prepared via the reaction of compound with -methoxy acetophenone, which in turn reacted with each of ethyl cyanoacetate, malononitrile, hydrazine hydrate, and thiosemicarbazide to afford the corresponding pyridine and pyrazole derivatives , , and The structure of newly synthesized compounds was characterized by analytical and spectroscopic data (IR, MS and NMR) All new compounds were evaluated against 5α-reductase and aromatase inhibitors and the results showed that many of these compounds inhibit 5α-reductase and aromatase activity; compound was found to be the highest potency among the tested samples comparing with the reference drugs.
这项工作描述了吡唑-4-甲醛作为起始原料，用于合成一系列新型强效的 5α-还原酶和芳香酶抑制剂，这些抑制剂衍生自 1,2,3-三唑衍生物。与活性亚甲基和不同的氨基吡唑缩合，分别得到相应的席夫碱-、和-。另一方面，与氰基乙酸乙酯和硫脲在一锅反应中反应，得到吡唑并-6-硫代-2-[3]-酮（）。此外，通过化合物与-甲氧基苯乙酮的反应制备了α-β 不饱和查耳酮衍生物，其又与氰基乙酸乙酯、丙二腈、水合肼和氨基硫脲反应，得到相应的吡啶和吡唑衍生物-、-、-和-。新合成化合物的结构通过分析和光谱数据（IR、MS 和 NMR）进行了表征。所有新化合物都针对 5α-还原酶和芳香酶抑制剂进行了评估，结果表明，这些化合物中有许多抑制 5α-还原酶和芳香酶活性；与参比药物相比，化合物被发现是测试样品中活性最高的一种。
