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二氢嘧啶及其区域选择性氧化产物的合成、晶体结构与抗菌研究

Synthesis, crystal structure and antibacterial studies of dihydropyrimidines and their regioselectively oxidized products.

作者信息

Huseynzada Alakbar E, Jelch Christian, Akhundzada Haji Vahid N, Soudani Sarra, Ben Nasr Cherif, Israyilova Aygun, Doria Filippo, Hasanova Ulviyya A, Khankishiyeva Rana F, Freccero Mauro

机构信息

Baku State University, ICRL Z. Khalilov 23 Baku AZ 1148 Azerbaijan

Université de Lorraine, CNRS, CRM2 54000 Nancy France.

出版信息

RSC Adv. 2021 Feb 3;11(11):6312-6329. doi: 10.1039/d0ra10255e. eCollection 2021 Feb 2.

DOI:10.1039/d0ra10255e
PMID:35423136
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC8694924/
Abstract

The syntheses and investigations of new biologically active derivatives of dihydropyrimidines by Biginelli reaction in the presence of copper triflate are reported. Due to the fact that salicylaldehyde and its derivatives under Biginelli reaction conditions can lead to the formation of 2 types of dihydropyrimidines, the influence of copper triflate on product formation was also investigated. In addition to this, regioselective oxidation of dihydropyrimidines was performed in the presence of cerium ammonium nitrate and novel oxidized dihydropyrimidines were obtained. Single crystals of some of them were obtained and as a result, the structures of them were investigated by X-ray diffraction method, which allows determining the presence of hydrogen bonds in their structures. In addition to this, the presence of hydrogen bonds in their structures affects the formation of the corresponding tautomer during oxidizing of dihydropyrimidines. Since dihydropyrimidines are claimed to be biologically active compounds, activities of the synthesized compounds were studied against , , , and bacteria.

摘要

报道了在三氟甲磺酸铜存在下通过Biginelli反应合成和研究新型生物活性二氢嘧啶衍生物。由于水杨醛及其衍生物在Biginelli反应条件下可导致形成2种类型的二氢嘧啶，因此还研究了三氟甲磺酸铜对产物形成的影响。除此之外，在硝酸铈铵存在下进行了二氢嘧啶的区域选择性氧化，并获得了新型氧化二氢嘧啶。获得了其中一些的单晶，结果通过X射线衍射法研究了它们的结构，这使得能够确定其结构中氢键的存在。除此之外，它们结构中氢键的存在会影响二氢嘧啶氧化过程中相应互变异构体的形成。由于二氢嘧啶据称是生物活性化合物，因此研究了合成化合物对 、 、 、 和 细菌的活性。

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