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Evaluation of Antibacterial, Cytotoxicity, and Apoptosis Activity of Novel Chromene-Sulfonamide Hybrids Synthesized Under Solvent-Free Conditions and 3D-Qsar Modeling Studies Publisher Pubmed



Ghomashi S1 ; Ghomashi R2 ; Damavandi MS3, 4 ; Fakhar Z5 ; Mousavi SY6 ; Salarijazi A7, 8 ; Gharaghani S5 ; Massah AR9, 10
Authors
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Authors Affiliations
  1. 1. Department of Medicinal Chemistry, Shahreza Branch, Islamic Azad University, Isfahan, Shahreza, Iran
  2. 2. Department of Medicinal Chemistry, School of Pharmacy and Pharmaceutical Sciences, Isfahan University of Medical Sciences, Isfahan, Iran
  3. 3. Department of Microbiology and Virology, Faculty of Medicine, Mashhad University of Medical Sciences, Mashhad, Iran
  4. 4. Antimicrobial Resistance Research Center, Mashhad University of Medical Sciences, Mashhad, Iran
  5. 5. Laboratory of Bioinformatics and Drug Design (LBD), Institute of Biochemistry and Biophysics, University of Tehran, Tehran, Iran
  6. 6. Department of Animal Biology, Faculty of Natural Sciences, University of Tabriz, Tabriz, Iran
  7. 7. Faculty of Medicine and Health Technology, Tampere University, Tampere, Finland
  8. 8. Department of Drug Development and Innovation, Behban Pharmed Lotus, Tehran, Iran
  9. 9. Department of Chemistry, Shahreza Branch, Islamic Azad University, Isfahan, Shahreza, Iran
  10. 10. Department of Chemistry, Brock University, St. Catharines, ON, Canada

Source: Scientific Reports Published:2024


Abstract

In this study, eleven novel chromene sulfonamide hybrids were synthesized by a convenient method in accordance with green chemistry. At first, chromene derivatives (1–9a) were prepared through the multi-component reaction between aryl aldehydes, malononitrile, and 3-aminophenol. Then, synthesized chromenes were reacted with appropriate sulfonyl chlorides by grinding method to give the corresponding chromene sulfonamide hybrids (1–11b). Synthesized hybrids were obtained in good to high yield and characterized by IR, 1HNMR, 13CNMR, CHN and melting point techniques. In addition, the broth microdilution assay was used to determine the minimal inhibitory concentration of newly synthesized chromene-sulfonamide hybrids. The MTT test was used to determine the cytotoxicity and apoptotic activity of the newly synthesized compounds against fibroblast L929 cells. The 3D‑QSAR analysis confirmed the experimental assays, demonstrating that our predictive model is useful for developing new antibacterial inhibitors. Consequently, molecular docking studies were performed to validate the findings of the 3D-QSAR analysis, confirming the potential binding interactions of the synthesized chromene-sulfonamide hybrids with the target enzymes. Molecular docking studies were employed to support the 3D-QSAR predictions, providing insights into the binding interactions between the newly synthesized chromene-sulfonamide hybrids and their target bacterial enzymes, thereby reinforcing the potential efficacy of these compounds as antibacterial agents. Also, some of the experimental outcomes supported or conflicted with the pharmacokinetic prediction (especially about compound carcinogenicity). The performance of ADMET predictor results was assessed. The work presented here proposes a computationally driven strategy for designing and discovering a new sulfonamide scaffold for bacterial inhibition. © The Author(s) 2024.
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