Synthesis, Characterization of Novel Fused Thiabenzene-1-Methyl-1-Oxide Analogs: DFT Computational, in Silico Molecular Docking Studies and Its Antibacterial Activity

• Published in: Polycyclic aromatic compounds 2023-02, Vol.43 (2), p.1395-1406
• Main Authors: Sathish Kumar, S., Venkatasubramanian, H., Jayaprakash, R., Mahasampath Gowri, S., Kutti Rani, S.
• Format: Article
• Language: English
• Subjects: Analogs; anti-MRSA activity; Antibacterial activity; Chemical synthesis; Computer applications; Density functional theory; Developing countries; DFT studies; DIMSOY; Drug development; fused thiabenzene-1-methyl-1-oxide; Infectious diseases; LDCs; Methicillin; Molecular docking; molecular docking studies; Multidrug resistance; NMR; Nuclear magnetic resonance; Staphylococcus aureus; Staphylococcus infections; Sulfur ylides; thiabenzene-S-oxide; tRNA; Tyrosine-tRNA ligase
• ISSN: 1040-6638; 1563-5333
• DOI: 10.1080/10406638.2022.2027793

The novel and fused thiabenzene-1-methyl-1-oxide analogs (5a-e) were synthesized by the reaction of Dimethylsulfoxoniummethylide (DIMSOY) and 4-alkoxy-2H-chromene-carboxaldehydes with cyclic Michel acceptors and having a leaving group at β-position. The compounds thus prepared were characterized by mass analysis, 1 H and 13 C NMR techniques and screened for their antibacterial activity by in vitro and in silico studies. The antibacterial activity of all the purified analogs (5a-e) were determined for Methicillin-resistant Staphylococcus aureus (MRSA) by disk diffusion technique. Molecular docking studies for these compounds (5a-e) were performed against Tyrosyl-tRNA synthetase inhibitor using AutoDock. Also discussed the Density functional theory (DFT) computational studies for these compounds (5a-e). Infectious diseases caused by MDRB (multidrug resistant bacteria) are an important problem to be addressed globally. They have been among the leading causes of death, disability, growing challenges to health security and human progress, especially in developing countries for centuries. The inspiring preliminary results of these fused thisbenzene-1-methyl-1-oxide analogs (5a-e), upon further modification will produce a best drug candidate having anti-MRSA activity.