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Synthesis, antitumor activity, enzyme assay, DNA binding and molecular docking of Bis -Schiff bases of pyrazoles
Journal of the Iranian Chemical Society ( IF 2.2 ) Pub Date : 2020-07-22 , DOI: 10.1007/s13738-020-02004-y
Nesrin M. Morsy , Ashraf S. Hassan , Taghrid S. Hafez , Mohamed R. H. Mahran , Inass A. Sadawe , Abdul M. Gbaj

A novel series of Bis-Schiff bases of pyrazoles 924 were synthesized by the direct condensation of 5-aminopyrazoles 4ad with dialdehydes 8ad in ethanol. The newly synthesized Bis-Schiff bases of pyrazoles 924 were characterized and confirmed by analytical and spectroscopic data. Some selected Bis-Schiff bases were investigated for their in vitro anti-proliferation activity toward three human carcinoma cell lines {HepG2 (liver), MCF-7 (breast) and RPE-1 (normal retina pigmented epithelium)} using MTT assay. The result in vitro showed that the compound 23 was found to be the active candidate against HepG2 and MCF-7 cells, while compound 16 was found to be the most potent derivative against RPE-1 cells. All the Bis-Schiff bases of pyrazoles 924 were evaluated for their screening on thymidine phosphorylase and DNA binding energy. The DNA binding energy showed that the compound 12 shows the lowest IC50 compared to other series of compounds and is the nearest one to the IC50 of the standard taxol. The molecular docking of the new Bis-Schiff base 9 was carried out and showed good binding energies (− 4.45, − 4.95, − 2.62, − 3.83 and − 5.03 kcal/mol with 1bna, 102d, 1k2j, 2gvr and 2des double-strand DNA targets, respectively) when compared to standard doxorubicin. This study is an introduction to promising compounds.



中文翻译:

吡唑的双-席夫碱的合成,抗肿瘤活性,酶法测定,DNA结合和分子对接

一种新颖的一系列吡唑的-Schiff碱9 - 24由5-氨基吡唑的直接缩合合成4A - d与二醛图8a - d乙醇。新合成的吡唑类的-Schiff碱9 - 24进行了表征,并通过分析和光谱数据确认。使用MTT测定法研究了一些选定的Bis- Schiff碱基对三种人类癌细胞系(HepG2(肝),MCF-7(乳腺癌)和RPE-1(正常视网膜色素上皮))的体外抗增殖活性。体外结果表明该化合物发现23是对抗HepG2和MCF-7细胞的活性候选物,而发现化合物16是对抗RPE-1细胞的最有效衍生物。所有吡唑-Schiff基地9 - 24它们对胸苷磷酸化酶和DNA结合能筛选评估。DNA结合能表明,与其他系列化合物相比,化合物12的最低IC 50值与标准紫杉醇的IC 50值最接近。新的Bis -Schiff base 9的分子对接与标准的阿霉素相比,具有1bna,102d,1k2j,2gvr和2des双链DNA靶标的结合能(分别为-4.45,-4.95,-2.62,-3.83和-5.03 kcal / mol)分别显示。这项研究是对有前途的化合物的介绍。

更新日期:2020-07-22
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