ArticleRSC advances2019
Highly efficient microwave synthesis of rhodanine and 2-thiohydantoin derivatives and determination of relationships between their chemical structures and antibacterial activity.
Article in RSC advances, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 15 papers.
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Who cites it
15 citing papers in PubMed.
- Design, synthesis and multitarget evaluation of cyclopropyl-appended thiohydantoin derivatives as dual cholinesterase and COX inhibitors with antioxidant activity: a combined experimental and computational study.Journal of computer-aided molecular design · 2026Article
- Overcoming Photodynamic Therapy Resistance: GSH-Responsive AIE Photosensitizer-Hydroxycamptothecin Nanoliposomes for Extrahepatic Cholangiocarcinoma.Advanced healthcare materials · 2026Article
- Microwave-Assisted One-Pot Synthetic Pathways for Pyrido[2,3-The Journal of organic chemistry · 2026Article
- Pd-, Cu-, and Ni-Catalyzed Reactions: A Comprehensive Review of the Efficient Approaches towards the Synthesis of Antibacterial Molecules.Pharmaceuticals (Basel, Switzerland) · 2024Review
- Synthesis of bis-thiohydantoin derivatives as an antiproliferative agents targeting EGFR inhibitory pathway.Molecular diversity · 2024Article
- Synthesis and Identification of Heterobivalent Anticancer Compounds Containing Urea and 5-Arylidene-2-Thiohydantoin Motifs.ChemistrySelect · 2024Article
- How Can Deep Eutectic Systems Promote Greener Processes in Medicinal Chemistry and Drug Discovery?Pharmaceuticals (Basel, Switzerland) · 2024Review
- Gastroprotective effect of rhodanine and 2,4-thiazolidinediones scaffolds in rat stomachs by contribution of anti-apoptotic (BCL-2) and tumor suppressor (P53) proteins.Scientific reports · 2024Article
- Chalcogen-Varied Imidazolone Derivatives as Antibiotic Resistance Breakers inAntibiotics (Basel, Switzerland) · 2023Article
- Development of Novel 1,3-Disubstituted-2-Thiohydantoin Analogues with Potent Anti-Inflammatory Activity;Molecules (Basel, Switzerland) · 2022Article
- One-Pot High-throughput Synthesis ofTetrahedron letters · 2022Article
- Discovery of Cinnamylidene Derivative of Rhodanine with High Anthelmintic Activity againstMolecules (Basel, Switzerland) · 2022Article
- A wearable AIEgen-based lateral flow test strip for rapid detection of SARS-CoV-2 RBD protein and N protein.Cell reports. Physical science · 2022Article
- Preliminary Studies of Antimicrobial Activity of New Synthesized Hybrids of 2-Thiohydantoin and 2-Quinolone Derivatives Activated with Blue Light.Molecules (Basel, Switzerland) · 2022Article
- 2-Thiohydantoin Moiety as a Novel Acceptor/Anchoring Group of Photosensitizers for Dye-Sensitized Solar Cells.Materials (Basel, Switzerland) · 2020Article
Corrections and comments
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Authors and funding
9 authors.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Here we report studies on the synthesis of 12 new heterocyclic derivatives that differ in three structural motifs and the simultaneous evaluation of the impact of these three variables on the biological properties. The examined compounds are based on rhodanine and 2-thiohydantoin cores equipped with hydrogen or carboxymethyl substituents at the N-3 position and linked to a triphenylamine moiety through 1,4-phenylene, 1,4-naphthalenylene and 1,9-anthracenylene spacers at the C-5 position of the heterocycles. All the compounds were synthesized very quickly, selectively and in high yields according to the developed microwave-assisted Knoevenagel condensation protocol, and they were characterized thoroughly with NMR, FT-IR and ESI-HRMS techniques. The derivatives were tested for their activity against selected strains of Gram-positive and Gram-negative bacteria and yeast. Two compounds showed good activity against Gram-positive bacteria, and all of them showed low cytotoxicity against three cell lines of the human immune system. Based on membrane permeability assays it was demonstrated that the active compounds do not penetrate the cell membrane, and thus they must act on the bacterial cell surface. Finally, we proved that the evaluated structure modifications had a synergistic effect and the simultaneous presence of a 1,4-phenylene spacer and carboxymethyl group at N-3 caused the highest boost in antimicrobial activity.
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Registered trials
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