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Synthesis 2025; 57(04): 784-799
DOI: 10.1055/s-0043-1775425
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Synthesis, In Vitro, and In Silico Approach to Quinoline-Arylsulfonate Derivatives as Antimicrobial Agents: DFT, Molecular Docking, and ADMET Studies

Sabahat Samreen
a   Department of Chemistry, Jamia Millia Islamia, Jamia Nagar, New Delhi 110025, India
,
Shabana Khatoon
b   Department of Biosciences, Jamia Millia Islamia, Jamia Nagar, New Delhi 110025, India
,
Saleem Javed
a   Department of Chemistry, Jamia Millia Islamia, Jamia Nagar, New Delhi 110025, India
,
Nafis Raj
b   Department of Biosciences, Jamia Millia Islamia, Jamia Nagar, New Delhi 110025, India
,
Nikhat Manzoor∗
b   Department of Biosciences, Jamia Millia Islamia, Jamia Nagar, New Delhi 110025, India
,
Afreen Inam∗
a   Department of Chemistry, Jamia Millia Islamia, Jamia Nagar, New Delhi 110025, India
› Author AffiliationsAfreen Inam acknowledges financial support UGC-BSR Research Start-up-Grant: F.No. 30-569/2021(BSR) from the University Grant Commission (UGC), Govt. of India. Sabahat Samreen acknowledges the University Grant Commission (UGC), Gov. of India for providing JRF and SRF Fellowships as financial support.
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Abstract

A series of novel 4-((7-chloroquinolin-4-yl)amino)phenyl arenesulfonates were synthesized via a two-step process and characterized by different spectroscopic technique for structural confirmation. The electronic structure of these derivatives was investigated by Density Functional Theory (DFT), a quantum mechanical method. All the derivatives were evaluated for their biological potency. The antibacterial activity was examined against a panel of bacteria, but they were found to be inactive. Antifungal examination demonstrated that these derivatives exhibited good to potent efficacy against fungal strain Candida albicans. Five derivatives had better MIC values between 125–250 μg/mL among all the synthesized compounds. These derivatives inhibited the formation and development of biofilms and other virulence factors of C. albicans such as adhesion and extracellular secreted proteinases and phospholipases. Furthermore, the result showed that these derivatives have low toxicity against human RBC cells. An in silico docking study showed a good binding energy with Als3 protein (PDB ID: 4LE8) and Sap2 protein (PDB ID: 1EAG) for 4-((7-chloroquinolin-4-yl)amino)phenyl 4-isopropylbenzenesulfonate and 4-((7-chloroquinolin-4-yl)amino)phenyl 4-methoxybenzenesulfonate. Considering the inhibitory effects of these derivatives against C. albicans, they can be used as potential candidates for antifungal development.

Key words

quinoline - sulfonyl ester - DFT study - antimicrobial - Candida albicans - hemolysis assay

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0043-1775425. Included are general information, antifungal activity of compounds (Figure S1), proteinase secretion (Figure S2), spectral data, copy of 1H NMR and 13C NMR spectra (Figure S3 – Figure S13), and LCMS spectra (Figure S14 – Figure S24) of synthesized compounds (QL1 -QL11) (PDF).
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Publication History

Received: 08 October 2024

Accepted after revision: 29 November 2024

Article published online:
07 January 2025

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