Facile green in situ hemisynthesis of new chiral chromeno-pyrimidine derivatives: antibacterial, antioxidant activities and molecular docking study

IF 1.9 3区化学 Q3 CHEMISTRY, APPLIED

Natural Product Research Pub Date : 2025-02-16 DOI:10.1080/14786419.2023.2290148

Ramzi Maadadi , Abbes Benmerache , Rafik Menacer , Borhane E.C Ziani , Zahia Kabouche , Liza Saher , Khaldoun Bachari , Dominique Harakat

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引用次数: 0

Abstract

A hemisynthesis ‘in situ’ reaction of (thio)barbituric acids with an α,β-unsaturated aldehyde using perillaldehyde from Ammodaucus leucotrichus essential oil, afforded chromeno-pyrimidine derivatives B-1 and B-2. The reaction was carried out in water and water/ethanol medium without a catalyst. The obtained pyrimidines were identified by their spectral ¹H,¹³C, Dept-135, HMBC, HSQC, COSY, and NOESY 2D. The antioxidant activity of both compounds was evaluated using different in vitro methods (DPPH, ABTS, and CUPRAC). The hemisynthesized molecules exhibited a bacteriostatic effect against ten tested gram (+) and gram (–) strains. According to the molecular docking analysis, B-1 showed lower binding energies compared to B-2 against (PDB: 1HD2) and (PDB: 1KZN) targets, which is in agreement with the ABTS and E. Coli assays. Furthermore, a probable promising anti-HIV activity was noticed against reverse transcriptase (PDB: 2RKI), a key enzyme for HIV replication. The ADME properties calculations showed no Lipinski’s rule violation for both compounds.

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新型手性色烯嘧啶衍生物的简便绿色原位半合成：抗菌、抗氧化活性和分子对接研究

利用从Ammodaucus leucotrichus精油中提取的perillaldehyde，对(硫)巴比妥酸与α,β-不饱和醛进行 "原位 "半合成反应，得到了铬嘧啶衍生物。

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来源期刊

Natural Product Research 化学-医药化学

CiteScore

5.10

自引率

9.10%

发文量

605

审稿时长

2.1 months

期刊介绍： The aim of Natural Product Research is to publish important contributions in the field of natural product chemistry. The journal covers all aspects of research in the chemistry and biochemistry of naturally occurring compounds. The communications include coverage of work on natural substances of land and sea and of plants, microbes and animals. Discussions of structure elucidation, synthesis and experimental biosynthesis of natural products as well as developments of methods in these areas are welcomed in the journal. Finally, research papers in fields on the chemistry-biology boundary, eg. fermentation chemistry, plant tissue culture investigations etc., are accepted into the journal. Natural Product Research issues will be subtitled either ""Part A - Synthesis and Structure"" or ""Part B - Bioactive Natural Products"". for details on this , see the forthcoming articles section. All manuscript submissions are subject to initial appraisal by the Editor, and, if found suitable for further consideration, to peer review by independent, anonymous expert referees. All peer review is single blind and submission is online via ScholarOne Manuscripts.