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4-(5-溴-1H-吲哚-3-基)-2,6-二甲基-1,4-二氢吡啶-3,5-二羧酸二乙酯的评估:合成、防腐潜力及生物医学应用

Evaluation of diethyl 4-(5-bromo-1H-indol-3-yl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate: synthesis, anti-corrosion potential, and biomedical applications.

作者信息

Ahamed F M Mashood, Padusha M Syed Ali, Banu A Mushira, Maitra Swastika, Alharbi Hanan M, Kumarasamy Vinoth, Uti Daniel E, Mohite Popat, Alexiou Athanasios, Ali Iftikhar

机构信息

PG and Research Department of Chemistry, Jamal Mohamed College (Autonomous), Affiliated to Bharathidasan University, Tiruchirappalli, Khajanagar, 620020, India.

Center for Global Health Research, Saveetha Medical College and Hospital, Saveetha Institute of Medical and Technical Sciences, Chennai, India.

出版信息

BMC Chem. 2024 May 10;18(1):98. doi: 10.1186/s13065-024-01123-4.

Abstract

The pursuit of advanced multifunctional compounds has gained significant momentum in recent scientific endeavours. This study is dedicated to elucidating the synthesis, rigorous characterization, and multifaceted applications-encompassing anti-corrosion, antimicrobial, and antioxidant properties-of Diethyl 4-(5-bromo-1H-indol-3-yl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate. The 1,4-dihydropyridine derivative was meticulously synthesized through a strategic reaction of ethyl acetoacetate, ammonium acetate, and 5-bromoindole-3-carboxaldehydein the ethanol medium at 60  C. Subsequent spectral validations were conducted using sophisticated techniques, namely FTIR, NMR, and Mass spectrometry, resulting in data that perfectly resonated with the hypothesized chemical structure of the compound. Its anti-corrosive potential was assessed on mild steel subjected to an aggressive acidic environment, employing comprehensive methodologies like gravimetric analysis, Tafel polarization, and EIS. Concurrently, its antimicrobial prowess was ascertained against a spectrum of bacterial and fungal pathogens viz., Staphylococcus aureus, Bacillus subtilis, Escherichia coli, Pseudomonas, Candida albicansandAspergillusniger, leveraging the disc diffusion method and using Gentamicin as a reference standard.The empirical results illustrated a substantial decrement in corrosion rates with ascending concentrations of the organic compound, achieving an apex of anti-corrosive efficacy at 81.89% for a concentration of 2 × 10 M. Furthermore, the compound outperformed Gentamicin in antimicrobial screenings, manifesting superior efficacy against all tested pathogens. The antioxidant potential, quantified using the DPPH free radical scavenging assay against ascorbic acid as a benchmark, was found to have an IC value of 113.964 ± 0.076 µg/ml.This comprehensive investigation accentuates the paramount potential of the synthesized dihydropyridine derivative in diverse domains-from industrial applications as a corrosion inhibitor to therapeutic avenues given its pronounced antimicrobial and antioxidant capabilities. The compelling results obtained pave the way for expansive research and development initiatives cantered around this multifaceted compound.

摘要

在最近的科学研究中,对先进多功能化合物的追求获得了巨大的发展势头。本研究致力于阐明4-(5-溴-1H-吲哚-3-基)-2,6-二甲基-1,4-二氢吡啶-3,5-二羧酸二乙酯的合成、严格表征及其多方面应用,包括防腐、抗菌和抗氧化性能。通过乙酰乙酸乙酯、乙酸铵和5-溴吲哚-3-甲醛在60℃乙醇介质中的策略性反应精心合成了1,4-二氢吡啶衍生物。随后使用傅里叶变换红外光谱(FTIR)、核磁共振(NMR)和质谱等先进技术进行光谱验证,所得数据与该化合物的假设化学结构完全吻合。在遭受侵蚀性酸性环境的低碳钢上评估其防腐潜力,采用了重量分析、塔菲尔极化和电化学阻抗谱(EIS)等综合方法。同时,利用纸片扩散法并以庆大霉素作为参考标准,确定其对一系列细菌和真菌病原体,即金黄色葡萄球菌、枯草芽孢杆菌、大肠杆菌、假单胞菌、白色念珠菌和黑曲霉的抗菌能力。实验结果表明,随着有机化合物浓度的增加,腐蚀速率大幅降低,在浓度为2×10⁻³M时防腐效果达到顶点,防腐效率为81.89%。此外,该化合物在抗菌筛选中表现优于庆大霉素,对所有测试病原体均表现出卓越的功效。以抗坏血酸为基准,使用DPPH自由基清除试验对其抗氧化潜力进行量化,发现其IC₅₀值为113.964±0.076μg/ml。这项全面的研究突出了合成的二氢吡啶衍生物在各个领域的巨大潜力——从作为缓蚀剂的工业应用到因其显著的抗菌和抗氧化能力而在治疗领域的应用。所获得的令人信服的结果为围绕这种多面化合物展开广泛的研发计划铺平了道路。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1abf/11084046/fc17631e1096/13065_2024_1123_Fig1_HTML.jpg

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