Straightforward synthesis, antiproliferative screening, and density functional theory study of some pyrazolylpyrimidine derivatives,Journal of Heterocyclic Chemistry

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Straightforward synthesis, antiproliferative screening, and density functional theory study of some pyrazolylpyrimidine derivatives
Journal of Heterocyclic Chemistry ( IF 2.0 ) Pub Date : 2020-12-09 , DOI: 10.1002/jhet.4204
Karema N. M. Halim ₁ , Sameh A. Rizk ₁ , Maher A. El‐Hashash ₁ , Sayed K. Ramadan ₁

Affiliation

Tetrahydropyrimidinone derivative was synthesized through one‐pot three components condensation of 1,3‐diphenylpyrazole‐4‐carbaldehyde with pentan‐2,4‐dione and urea under Biginelli reaction conditions. The corresponding chloro‐ and hydrazino derivatives were synthesized and utilized for the construction of some valuable N‐heterocycles encompassing both pyrazole and pyrimidine cores, such as triazolopyrimidine, tetrazolopyrimidine, pyrazole, and pyrazolone derivatives through condensation with nitrogen nucleophiles and carbon electrophiles. The antiproliferative activity evaluation of the synthesized compounds against four human carcinoma cell lines namely, liver carcinoma (HepG2), breast adenocarcinoma (MCF7), prostate cancer (PC3), and colon cancer (HCT‐116) cell lines revealed that some of them provided significant potency, as well as the density‐functional theory (DFT) was studied. The permeability of various hydrophilic and hydrophobic synthesized compounds across both normal and cancer cells is confirmed via DFT simulation in which the much higher permeability through aquaporin channels revealed the selective cytotoxicity toward cancer cells.

中文翻译：

吡唑基嘧啶衍生物的简单合成，抗增殖筛选和密度泛函理论研究

四氢嘧啶酮衍生物是通过Biginelli反应条件下的1,3-二苯并吡唑-4-甲醛与戊丹-2,4-二酮和尿素的一锅三组分缩合而合成的。合成了相应的氯代和肼代衍生物，并将其用于构建一些有价值的氮通过与氮亲核试剂和碳亲电子试剂缩合，涵盖吡唑和嘧啶核的杂环，例如三唑并嘧啶，四唑并嘧啶，吡唑和吡唑啉酮衍生物。合成化合物对肝癌细胞（HepG2），乳腺腺癌（MCF7），前列腺癌（PC3）和结肠癌（HCT-116）四种人癌细胞系的抗增殖活性评估表明，其中一些提供了研究了显着的效能以及密度泛函理论（DFT）。通过DFT模拟证实了各种亲水性和疏水性合成化合物在正常细胞和癌细胞中的渗透性，其中通过水通道蛋白通道的更高的渗透性揭示了对癌细胞的选择性细胞毒性。

更新日期：2021-02-12

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