ArticleBMC chemistry2024
New thiophene derivatives: chemoselective synthesis, antitumor effectiveness, structural characterization, DFT calculations, Hirshfeld surface, and Fukui function analysis.
Article in BMC chemistry, 2024. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 3 papers.
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Who cites it
3 citing papers in PubMed.
- Ethyl 4-oxo-2-(phenylamino)-4,5-dihydrothiophene-3-carboxylate: crystal structure, computational analysis, and drug likeness studies.BMC chemistry · 2026Article
- Synthetic Progress and Antifungal Potential of Thiophene Chalcone Derivatives: A Review.Current organic synthesis · 2026Review
- A Risk-Based Framework for Hospital Compounding: Integrating Degradation Mechanisms and Predictive Toxicology.Pharmaceutics · 2025Article
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Authors and funding
8 authors.
Funding
Abstract
In this study, the chemoselective synthesis of two new thiophene derivatives is presented. The structure of newly synthesized thiophenes derivatives; ethyl 4-acetyl-3-phenyl-5-(phenylamino)thiophene-2-carboxylate (5) and ethyl (E)-4-(3-(dimethylamino)acryloyl)-3-phenyl-5-(phenylamino)thiophene-2-carboxylate (8) were established using different FTIR and NMR spectral analyses. Compound 8 was isolated as single crystal and its 3D structure was determined using X-ray crystallographic analysis. Possible intermolecular interactions that control the molecular packing of 8 were elucidated using Hirshfeld topology analysis. The O…H (13.7%), H…H (55.3%) and C…C (2.3%) intermolecular interactions are the most significant. Fukui functions showed that C4 in thiophene 5 and C3 in thiophene 8 are the most reactive atoms for nucleophilic attack, while N9 in thiophene 5 and C1 in thiophene 8 are the most reactive atoms for electrophilic attack. Antitumor activity of thiophene 5 was assessed and the results showed higher activity against HepG-2 (7.46 µg/mL) compared to the HCT 116 (12.60 µg/mL) cell line.
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