Synthesis of novel heterocyclic compounds containing pyrimidine nucleus using the Biginelli reaction: Antiproliferative activity and docking studies,Journal of Heterocyclic Chemistry

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Synthesis of novel heterocyclic compounds containing pyrimidine nucleus using the Biginelli reaction: Antiproliferative activity and docking studies
Journal of Heterocyclic Chemistry ( IF 2.0 ) Pub Date : 2020-04-02 , DOI: 10.1002/jhet.3978
Sevtap Çağlar Yavuz _{1,

2} , Senem Akkoç ₃ , Burçin Türkmenoğlu ₄ , Emin Sarıpınar ₁

Affiliation

In a single reaction step, pyrimidine derivatives (4a‐p ) were synthesized from the triple reaction of aromatic aldehydes (1) , ethyl cyanoacetate (2) , and some guanyl hydrazone derivatives (3a‐n) . These compounds were tested as in vitro against two types of cancerous cell lines, namely, a human colon cancerous cell line (DLD‐1) and a human breast cancerous cell line (MDA‐MB‐231). According to the obtained results, nearly all the compounds have cytotoxic activity in the tested cell lines. Especially, the compounds 4j , 4k , and 4n had a significant effect against DLD‐1. Furthermore, compounds 4g , 4m , and 4o exhibited lower IC₅₀ values compared to other synthesized compounds against MDA‐MB‐231. We hope that these compounds can be improved as anticancer agents in the future. Molecular docking was performed according to both topoisomerase I and N ‐acetyltransferase 1 proteins to examine theoretically the binding mode and site of pyrimidine compounds having the best activity.

中文翻译：

利用Biginelli反应合成含有嘧啶核的新型杂环化合物：抗增殖活性和对接研究

在一个反应步骤中，由芳香醛（1），氰基乙酸乙酯（2）和一些some衍生物（3a-n）的三重反应合成了嘧啶衍生物（4a-p ）。这些化合物在体外针对两种类型的癌细胞系进行了测试，分别是人结肠癌细胞系（DLD-1）和人乳腺癌细胞系（MDA-MB-231）。根据获得的结果，几乎所有化合物在测试的细胞系中均具有细胞毒活性。尤其是化合物4j，4k和4n对DLD-1具有明显的影响。此外，化合物4g，4m，和4o相比，针对MDA-MB-231的其他合成化合物，IC ₅₀值更低。我们希望这些化合物将来可以作为抗癌药得到改进。根据拓扑异构酶I和N-乙酰转移酶1蛋白进行分子对接，从理论上检查具有最佳活性的嘧啶化合物的结合模式和位点。

更新日期：2020-04-02

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