Impact of S–N Bond Length, N→π* Interactions on the Stability, Reactivity, and Antibacterial Activity of 4-Amino-N-(4-methyl-2-pyrimidinyl)benzenesulfonamide: a Combined DFT, NBO, ELF, Vibrational, and Docking Analysis

IF 1.1 4区化学 Q4 CHEMISTRY, PHYSICAL

Doklady Physical Chemistry Pub Date : 2026-02-24 DOI:10.1134/S0012501625600640

M. Siva Priya, C. James, B. S. Arun Sasi, A. R. Twinkle, R. Reshma

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Abstract

This study explores the molecular structure, stability, reactivity, and antibacterial activity of sulfamerazine, a sulfonamide derivative, using computational and experimental approaches. Density functional theory (DFT) at the B3LYP/6-311+G(d,p) level was used to optimize geometry, analyze vibrational modes, and evaluate electronic properties. Key interactions such as S–N bond length, N→π* delocalization, and hydrogen bonding were found to influence antibacterial efficacy. Vibrational analysis and scaled quantum mechanical (SQM) methods revealed functional dynamics supporting molecular stability. Docking studies showed strong binding of sulfamerazine to bacterial enzymes, corroborated by in vitro assays against Staphylococcus aureus and Pseudomonas aeruginosa. Electron localization function (ELF) and natural bond orbital (NBO) analyses confirmed significant charge transfer and delocalization. Pharmacokinetic and toxicity evaluations supported its drug-likeness and safety. These results highlight sulfamerazine’s potential as a versatile antibacterial agent and provide insights for designing improved sulfonamide-based therapeutics.

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S-N键长、N→π*相互作用对4-氨基-N-（4-甲基-2-嘧啶基）苯磺酰胺稳定性、反应性和抗菌活性的影响：DFT、NBO、ELF、振动和对接分析

本研究通过计算和实验方法，探讨了磺胺衍生物磺胺嗪的分子结构、稳定性、反应性和抗菌活性。B3LYP/6-311+G（d,p）水平的密度泛函理论（DFT）被用于优化几何结构、分析振动模式和评估电子特性。发现S-N键长度、N→π*离域和氢键等关键相互作用影响抗菌效果。振动分析和尺度量子力学（SQM）方法揭示了支持分子稳定性的功能动力学。对接研究表明，磺胺美嗪与细菌酶有很强的结合，这一点在体外抗金黄色葡萄球菌和铜绿假单胞菌试验中得到了证实。电子局域函数（ELF）和自然键轨道（NBO）分析证实了明显的电荷转移和离域。药代动力学和毒性评价支持其药物相似性和安全性。这些结果突出了磺胺嗪作为一种多功能抗菌剂的潜力，并为设计改进的基于磺胺的治疗方法提供了见解。

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来源期刊

Doklady Physical Chemistry 化学-物理化学

CiteScore

1.50

自引率

0.00%

发文量

审稿时长

6-12 weeks

期刊介绍： Doklady Physical Chemistry is a monthly journal containing English translations of current Russian research in physical chemistry from the Physical Chemistry sections of the Doklady Akademii Nauk (Proceedings of the Russian Academy of Sciences). The journal publishes the most significant new research in physical chemistry being done in Russia, thus ensuring its scientific priority. Doklady Physical Chemistry presents short preliminary accounts of the application of the state-of-the-art physical chemistry ideas and methods to the study of organic and inorganic compounds and macromolecules; polymeric, inorganic and composite materials as well as corresponding processes. The journal is intended for scientists in all fields of chemistry and in interdisciplinary sciences.