Novel nosylation reagent mediated highly efficient synthesis, DFT approach and biological activities of sulfonamides

IF 1.7 3区化学 Q3 CHEMISTRY, MULTIDISCIPLINARY

Journal of Sulfur Chemistry Pub Date : 2026-01-02 Epub Date: 2025-11-13 DOI:10.1080/17415993.2025.2582553

Ravi Kumar Shekunti , Sudharshan Reddy Akkamolla , Nagelli Kishore , Sridhar Reddy Kothakapu , Annapurna Padmavathi Devarakonda

{"title":"Novel nosylation reagent mediated highly efficient synthesis, DFT approach and biological activities of sulfonamides","authors":"Ravi Kumar Shekunti , Sudharshan Reddy Akkamolla , Nagelli Kishore , Sridhar Reddy Kothakapu , Annapurna Padmavathi Devarakonda","doi":"10.1080/17415993.2025.2582553","DOIUrl":null,"url":null,"abstract":"<div><div>The study reports a highly efficient, eco-friendly method using a novel reagent, N-pyridinium nosyl chloride ([DMAPNS]+Cl-), for the rapid synthesis of sulfonamides under mild conditions. Equimolar reactions of the reagent with various amines in dichloromethane at room temperature were completed within 15 minutes, affording isolated yields of up to 97% without the need for chromatographic purification. Density functional theory (DFT) calculations at the B3LYP/6-311G level were performed to examine the electronic structures and reactivity of the pyridinium salts. Key quantum chemical parameters such as EHOMO, ELUMO, energy gap (ΔE), electron affinity (EA), ionization potential (IP), global electrophilicity index (ω), dipole moment (µ), softness (S), chemical hardness (η), and absolute electronegativity (χ) were evaluated to interpret molecular stability and reactivity trends. Among these, compound 18 exhibited the highest ionisation potential (7.84 eV) and hardness (2.05 eV), indicating enhanced chemical stability. . Antibacterial screening against selected MTCC and NCIM strains showed that compounds 4, 8, 12, 16 and 18 displayed strong broad-spectrum activity, while compounds 14, 20, and 22 exhibited moderate effects. The integration of synthetic methodology, quantum chemical analysis, and biological evaluation highlights the potential of this nosylation approach for the design of future sulfonamide-based therapeutics.</div></div>","PeriodicalId":17081,"journal":{"name":"Journal of Sulfur Chemistry","volume":"47 1","pages":"Pages 87-102"},"PeriodicalIF":1.7000,"publicationDate":"2026-01-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of Sulfur Chemistry","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/org/science/article/pii/S1741599325000583","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"2025/11/13 0:00:00","PubModel":"Epub","JCR":"Q3","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}

引用次数: 0

Abstract

The study reports a highly efficient, eco-friendly method using a novel reagent, N-pyridinium nosyl chloride ([DMAPNS]⁺Cl^-), for the rapid synthesis of sulfonamides under mild conditions. Equimolar reactions of the reagent with various amines in dichloromethane at room temperature were completed within 15 minutes, affording isolated yields of up to 97% without the need for chromatographic purification. Density functional theory (DFT) calculations at the B3LYP/6-311G level were performed to examine the electronic structures and reactivity of the pyridinium salts. Key quantum chemical parameters such as E_HOMO, E_LUMO, energy gap (ΔE), electron affinity (EA), ionization potential (IP), global electrophilicity index (ω), dipole moment (µ), softness (S), chemical hardness (η), and absolute electronegativity (χ) were evaluated to interpret molecular stability and reactivity trends. Among these, compound 18 exhibited the highest ionisation potential (7.84 eV) and hardness (2.05 eV), indicating enhanced chemical stability. . Antibacterial screening against selected MTCC and NCIM strains showed that compounds 4, 8, 12, 16 and 18 displayed strong broad-spectrum activity, while compounds 14, 20, and 22 exhibited moderate effects. The integration of synthetic methodology, quantum chemical analysis, and biological evaluation highlights the potential of this nosylation approach for the design of future sulfonamide-based therapeutics.

查看原文本刊更多论文

新型甲基化试剂介导的高效合成、DFT方法及磺胺类化合物的生物活性

该研究报告了一种高效、环保的方法，使用一种新型试剂n -吡啶甲基氯（[DMAPNS]+Cl-），在温和条件下快速合成磺胺类药物。该试剂在室温下与各种胺在二氯甲烷中进行等摩尔反应，在15分钟内完成，分离收率高达97%，无需进行色谱纯化。在B3LYP/6-311G水平上进行密度泛函理论（DFT）计算，考察了吡啶盐的电子结构和反应性。通过评价关键的量子化学参数，如EHOMO、ELUMO、能隙（ΔE）、电子亲和性（EA）、电离势（IP）、全局亲电性指数（ω）、偶极矩（µ）、柔软度(S)、化学硬度（η）和绝对电负性（χ）来解释分子的稳定性和反应性趋势。其中化合物18具有最高的电离电位（7.84 eV）和硬度（2.05 eV），表明化合物具有较强的化学稳定性。对选定的MTCC和NCIM菌株进行抗菌筛选，化合物4、8、12、16和18表现出较强的广谱活性，而化合物14、20和22表现出中等的广谱活性。合成方法、量子化学分析和生物学评价的整合突出了这种甲基化方法在设计未来基于磺胺的治疗方法方面的潜力。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

求助全文

约1分钟内获得全文求助全文

来源期刊

Journal of Sulfur Chemistry CHEMISTRY, MULTIDISCIPLINARY-

CiteScore

4.10

自引率

9.10%

发文量

审稿时长

6-12 weeks

期刊介绍： The Journal of Sulfur Chemistry is an international journal for the dissemination of scientific results in the rapidly expanding realm of sulfur chemistry. The journal publishes high quality reviews, full papers and communications in the following areas: organic and inorganic chemistry, industrial chemistry, materials and polymer chemistry, biological chemistry and interdisciplinary studies directly related to sulfur science. Papers outlining theoretical, physical, mechanistic or synthetic studies pertaining to sulfur chemistry are welcome. Hence the target audience is made up of academic and industrial chemists with peripheral or focused interests in sulfur chemistry. Manuscripts that truly define the aims of the journal include, but are not limited to, those that offer: a) innovative use of sulfur reagents; b) new synthetic approaches to sulfur-containing biomolecules, materials or organic and organometallic compounds; c) theoretical and physical studies that facilitate the understanding of sulfur structure, bonding or reactivity; d) catalytic, selective, synthetically useful or noteworthy transformations of sulfur containing molecules; e) industrial applications of sulfur chemistry; f) unique sulfur atom or molecule involvement in interfacial phenomena; g) descriptions of solid phase or combinatorial methods involving sulfur containing substrates. Submissions pertaining to related atoms such as selenium and tellurium are also welcome. Articles offering routine heterocycle formation through established reactions of sulfur containing substrates are outside the scope of the journal.