Molecular iodine catalyzed C(sp2)–H sulfenylation of biologically active enaminone compounds under mechanochemical conditions and studies on their biocidal activity including molecular docking and DFT

Here we demonstrated a solvent free, mechanochemical I 2 catalyzed C(sp2)–H sulfenylation of enaminones under grinding condition. Only catalytic amount of I 2 is required on silica surface without any external heating. The reaction time has reduced to a great extent in comparison to their solution b...

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Published in:Molecular diversity 2024-06, Vol.28 (3), p.1597-1607
Main Authors: Islam, Aminul, Choudhury, Prasun, Sarkar, Kaushik, Das, Rajesh Kumar, Bhattacharya, Malay, Ghosh, Pranab
Format: Article
Language:English
Subjects:
Anti-Bacterial Agents - chemical synthesis
Anti-Bacterial Agents - chemistry
Anti-Bacterial Agents - pharmacology
Antiparasitic agents
Bacteria - drug effects
Biochemistry
Biomedical and Life Sciences
Catalysis
Density Functional Theory
E coli
Iodine
Iodine - chemistry
Life Sciences
Malaria
Microbial Sensitivity Tests
Molecular Docking Simulation
Organic Chemistry
Original Article
Pharmacy
Pneumonia
Polymer Sciences
Solvents
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Summary:Here we demonstrated a solvent free, mechanochemical I 2 catalyzed C(sp2)–H sulfenylation of enaminones under grinding condition. Only catalytic amount of I 2 is required on silica surface without any external heating. The reaction time has reduced to a great extent in comparison to their solution based counterpart. The frictional energy created by ball-mill on mesoporous silica materials has attracted much attention towards this mechanochemical approach for molecular heterogeneous catalysis. Their large surface area and well defined porous architecture certainly increase the catalytic ability of iodine in this developed protocol. Anti-microbial activities of our synthesized compounds were investigated against two gram positive ( Staphylococcus aureus and Bacillus cereus ) and two gram negative ( Escherichia coli and Klebsiella pneumonia ) bacteria. To understand the potency of these compounds (3a–3m) as antimalarial agents, molecular docking studies were also performed. Density functional theory was also used to investigate the chemical reactivity and kinetic stability of the compound 3a–3m.
ISSN:1381-1991
1573-501X
1573-501X
DOI:10.1007/s11030-023-10677-9