A facile synthesis, biological evaluation, ADMET profiling and computational insights of novel triazole-linked tetrahydrobenzo[b]thiophenes: A sonochemical click synthetic strategy in recyclable ionic liquid medium.

Λεπτομέρειες βιβλιογραφικής εγγραφής
Τίτλος: A facile synthesis, biological evaluation, ADMET profiling and computational insights of novel triazole-linked tetrahydrobenzo[b]thiophenes: A sonochemical click synthetic strategy in recyclable ionic liquid medium.
Συγγραφείς: Kurahatti S; Department of Chemistry, Karnatak University's Karnatak Science College, Dharwad, Karnataka 580001, India., Kalkhambkar RG; Department of Chemistry, Karnatak University's Karnatak Science College, Dharwad, Karnataka 580001, India. Electronic address: rgkalkhambkar2020@gmail.com., Dalbanjan NP; Dr. Prabhakar Kore Basic Science Research Centre, KLE Academy of Higher Education and Research (Deemed to be University), Nehru Nagar, Belagavi, Karnataka 590010, India.
Πηγή: Bioorganic chemistry [Bioorg Chem] 2026 Oct 05; Vol. 181, pp. 110286. Date of Electronic Publication: 2026 Jul 28.
Τύπος έκδοσης: Journal Article
Γλώσσα: English
Στοιχεία περιοδικού: Publisher: Elsevier Country of Publication: United States NLM ID: 1303703 Publication Model: Print-Electronic Cited Medium: Internet ISSN: 1090-2120 (Electronic) Linking ISSN: 00452068 NLM ISO Abbreviation: Bioorg Chem Subsets: MEDLINE
Imprint Name(s): Publication: Amsterdam : Elsevier
Original Publication: New York, London, Academic Press.
Ιατρικοί όροι (MeSH): Ionic Liquids*/chemistry , Triazoles*/chemistry , Triazoles*/pharmacology , Thiophenes*/pharmacology , Thiophenes*/chemistry , Thiophenes*/chemical synthesis , Anti-Bacterial Agents*/pharmacology , Anti-Bacterial Agents*/chemical synthesis , Anti-Bacterial Agents*/chemistry , Antifungal Agents*/pharmacology , Antifungal Agents*/chemical synthesis , Antifungal Agents*/chemistry , Antioxidants*/pharmacology , Antioxidants*/chemical synthesis , Antioxidants*/chemistry, Staphylococcus aureus/drug effects ; Candida albicans/drug effects ; Escherichia coli/drug effects ; Candida glabrata/drug effects ; Biphenyl Compounds/antagonists & inhibitors ; Microbial Sensitivity Tests ; Molecular Structure ; Click Chemistry ; Structure-Activity Relationship ; Molecular Docking Simulation ; Dose-Response Relationship, Drug
Περίληψη: A series of novel 1,2,3-triazole-linked tetrahydrobenzo[b]thiophene derivatives were synthesized through a Green and sustainable sonochemical protocol by employing copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC) in a recyclable [BMIM][BF4]/ H2O (1:1) medium to explore their antimicrobial and antioxidant potential. The method features mild reaction conditions, excellent yields and notably, the ionic liquid (IL) employed was effectively recycled for five runs without significant loss of its efficiency. A comparative study under conventional conditions also demonstrated improved green metrics, such as high atom economy (100%) and reaction mass efficiency (94%), and low E-factor (0.064) and process mass intensity (1.06). The in-vitro biological assessment showed significant antimicrobial potency of these compounds, compound 3a demonstrated the highest potency against Staphylococcus aureus and Escherichia coli, with a low MIC value of 8 μg/mL, as well as activity against Candida albicans and Candida glabrata (MIC = 16 μg/mL). Additionally, antioxidant assays revealed moderate free-radical scavenging activity for compound 3c. Molecular docking simulation validated the binding interaction of the synthesized molecules with selected key proteins. This supports the proposed mechanism of action, as stable binding was observed in the target protein's active site. Moreover, ADMET analysis revealed that the synthesized compounds have good drug-like properties, which include efficient gastrointestinal absorption and adherence to Lipinski's rule. Overall, the present study describes an environmentally friendly approach with significant biological potential of designed scaffolds.
(Copyright © 2026 Elsevier Inc. All rights reserved.)
Competing Interests: Declaration of competing interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper.
Contributed Indexing: Keywords: Click chemistry; Green chemistry; Ionic liquids; Sonochemistry; Thiophenes; Triazoles; Ultrasonication
Substance Nomenclature: 0 (Ionic Liquids)
0 (Triazoles)
0 (Thiophenes)
0 (Anti-Bacterial Agents)
0 (Antifungal Agents)
0 (Antioxidants)
0 (Biphenyl Compounds)
Entry Date(s): Date Created: 20260801 Date Completed: 20260909 Latest Revision: 20260909
Update Code: 20260909
DOI: 10.1016/j.bioorg.2026.110286
PMID: 42542009
Βάση Δεδομένων: MEDLINE
Περιγραφή
ISSN:1090-2120
DOI:10.1016/j.bioorg.2026.110286