Antibacterial efficacy of pyranopyrimidinone derivatives synthesized using a facile one-pot reaction

IF 2.8 3区化学 Q2 CHEMISTRY, MULTIDISCIPLINARY Research on Chemical Intermediates Pub Date : 2024-07-03 DOI:10.1007/s11164-024-05337-y

Nasrin Saberi Harooni, Fatemeh Dehghani Tafti, Nazanin Moghaddam, Hossein Naeimi, Parisa Azerang, Azar Tahghighi

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Abstract

Discovering new and effective medications against resistant bacteria is an urgent need to save modern medicine, as well as prevent and treat life-threatening diseases. This study aimed to synthesize a series of pyrano[2,3-d]pyrimidinone derivatives using a Tandem Knoevenagel-Michael cyclocondensation reaction. All the synthetic compounds were screened for antibacterial activity against various bacterial strains and isolates. Compound 7‐amino‐6‐cyano‐5-(5-nitrofuran-2-yl)‐pyrano[2,3-d]pyrimidin‐(1H,3H)-2,4‐diones (4s) showed superb antibacterial activities against Staphylococcus aureus, Bacillus subtilis, and Escherichia coli with a minimum inhibitory concentration (MIC) ranging from 3.91 to 7.81 μg/mL. This compound also exhibited more potent antibacterial activity than levofloxacin against methicillin-resistant S. aureus (MRSA) with a MIC value of 3.91 μg/mL and demonstrated relatively no cytotoxicity at the mentioned MIC concentration. Field-emission scanning electron microscopy (FE-SEM) confirmed the complete damage of S. aureus and E. coli following exposure to compound 4s. The compound 4s has the potential to be used as an alternative antibacterial drug after supplementary studies.

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利用简单的一锅反应合成的吡喃嘧啶酮衍生物的抗菌功效

要拯救现代医学，预防和治疗危及生命的疾病，迫切需要发现针对耐药细菌的有效新药。本研究旨在利用串联 Knoevenagel-Michael 环缩合反应合成一系列吡喃并[2,3-d]嘧啶酮衍生物。对所有合成化合物进行了筛选，以检测其对各种细菌菌株和分离物的抗菌活性。化合物 7-氨基-6-氰基-5-(5-硝基呋喃-2-基)-吡喃并[2,3-d]嘧啶-(1H,3H)-2,4-二酮（4s）对金黄色葡萄球菌、枯草杆菌和大肠杆菌具有极强的抗菌活性，最低抑菌浓度（MIC）为 3.91 至 7.81 μg/mL。该化合物对耐甲氧西林金黄色葡萄球菌（MRSA）的 MIC 值为 3.91 μg/mL，比左氧氟沙星具有更强的抗菌活性，而且在上述 MIC 浓度下相对没有细胞毒性。场发射扫描电子显微镜（FE-SEM）证实，金黄色葡萄球菌和大肠杆菌在接触化合物 4s 后完全受损。经补充研究后，化合物 4s 有潜力用作替代抗菌药物。

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来源期刊

Research on Chemical Intermediates 化学-化学综合

CiteScore

5.70

自引率

18.20%

发文量

229

审稿时长

2.6 months

期刊介绍： Research on Chemical Intermediates publishes current research articles and concise dynamic reviews on the properties, structures and reactivities of intermediate species in all the various domains of chemistry. The journal also contains articles in related disciplines such as spectroscopy, molecular biology and biochemistry, atmospheric and environmental sciences, catalysis, photochemistry and photophysics. In addition, special issues dedicated to specific topics in the field are regularly published.