ArticleInternational journal of molecular sciences2022
Synthesis, Crystallographic, Quantum Chemical, Antitumor, and Molecular Docking/Dynamic Studies of 4-Hydroxycoumarin-Neurotransmitter Derivatives.
Article in International journal of molecular sciences, 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 16 papers.
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Who cites it
16 citing papers in PubMed, 42 citations in OpenAlex.
- Advances in 4-Hydroxycoumarin Chemistry: Functionalization, Prominent 4-Hydroxycoumarin-based Therapeutics and their Pharmacological Significance.Mini reviews in medicinal chemistry · 2026Review
- The Therapeutic Potential ofMolecules (Basel, Switzerland) · 2025Article
- Coumarins in Anticancer Therapy: Mechanisms of Action, Potential Applications and Research Perspectives.Pharmaceutics · 2025Review
- Unexpected discovery: "A new 3,3'-bipyrazolo[3,4-Heliyon · 2024Article
- Trimethyltin(IV) Bearing 3-(4-Methyl-2-oxoquinolin-1(2H)-yl)propanoate Causes Lipid Peroxidation-Mediated Autophagic Cell Death in Human Melanoma A375 Cells.Pharmaceuticals (Basel, Switzerland) · 2024Article
- Synthesis of Chroman-2,4-diones via Ring-Opening/Ring-Closing Reaction Involving Palladium-Catalyzed Intramolecular Aryloxycarbonylation.The Journal of organic chemistry · 2024Article
- Synthesis, Structural Characterization, Cytotoxicity, and Protein/DNA Binding Properties of Pyridoxylidene-Aminoguanidine-Metal (Fe, Co, Zn, Cu) Complexes.International journal of molecular sciences · 2023Article
- The Effect of Metal Ions (Fe, Co, Ni, and Cu) on the Molecular-Structural, Protein Binding, and Cytotoxic Properties of Metal Pyridoxal-Thiosemicarbazone Complexes.International journal of molecular sciences · 2023Article
- Coumarin-Based Compounds as Inhibitors of Tyrosinase/Tyrosine Hydroxylase: Synthesis, Kinetic Studies, and In Silico Approaches.International journal of molecular sciences · 2023Article
- Synthesis and Cytotoxicity Evaluation of Novel Coumarin-Palladium(II) Complexes against Human Cancer Cell Lines.Pharmaceuticals (Basel, Switzerland) · 2022Article
- Antibacterial Activity ofMolecules (Basel, Switzerland) · 2022Article
- Influence of the Active Site Flexibility on the Efficiency of Substrate Activation in the Active Sites of Bi-Zinc Metallo-β-Lactamases.Molecules (Basel, Switzerland) · 2022Article
- Identification of MiRNA-Disease Associations Based on Information of Multi-Module and Meta-Path.Molecules (Basel, Switzerland) · 2022Article
- Electrochemotherapy of Primary Colon Rectum Cancer and Local Recurrence: Case Report and Prospective Analysis.Journal of clinical medicine · 2022Article
- Photodegradation and In Silico Molecular Docking Study of a Diuretic Drug: Clopamide.ACS omega · 2022Article
- Newly Synthesized Thymol Derivative and Its Effect on Colorectal Cancer Cells.Molecules (Basel, Switzerland) · 2022Article
Corrections and comments
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Authors and funding
11 authors at 6 institutions in 5 countries.
Funding
Abstract
In this contribution, four new compounds synthesized from 4-hydroxycoumarin and tyramine/octopamine/norepinephrine/3-methoxytyramine are characterized spectroscopically (IR and NMR), chromatographically (UHPLC-DAD), and structurally at the B3LYP/6-311++G*(d,p) level of theory. The crystal structure of the 4-hydroxycoumarin-octopamine derivative was solved and used as a starting geometry for structural optimization. Along with the previously obtained 4-hydroxycoumarin-dopamine derivative, the intramolecular interactions governing the stability of these compounds were quantified by NBO and QTAIM analyses. Condensed Fukui functions and the HOMO-LUMO gap were calculated and correlated with the number and position of OH groups in the structures. In vitro cytotoxicity experiments were performed to elucidate the possible antitumor activity of the tested substances. For this purpose, four cell lines were selected, namely human colon cancer (HCT-116), human adenocarcinoma (HeLa), human breast cancer (MDA-MB-231), and healthy human lung fibroblast (MRC-5) lines. A significant selectivity towards colorectal carcinoma cells was observed. Molecular docking and molecular dynamics studies with carbonic anhydrase, a prognostic factor in several cancers, complemented the experimental results. The calculated MD binding energies coincided well with the experimental activity, and indicated 4-hydroxycoumarin-dopamine and 4-hydroxycoumarin-3-methoxytyramine as the most active compounds. The ecotoxicology assessment proved that the obtained compounds have a low impact on the daphnia, fish, and green algae population.
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Registered trials
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