Quantitative relationships between structure and cytotoxic activity of flavonoid derivatives. An application of Hirshfeld surface derived descriptors
| Autor: | Urszula Krajewska, Mariusz Zapadka, Bogumiła Kupcewicz, Elzbieta Budzisz, Marek Rozalski, Magdalena Małecka |
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| Rok vydání: | 2016 |
| Předmět: |
Quantitative structure–activity relationship
Surface Properties Stereochemistry Clinical Biochemistry Pharmaceutical Science chemistry.chemical_element Antineoplastic Agents HL-60 Cells Pyrazoline 010402 general chemistry 01 natural sciences Biochemistry Cell Line Structure-Activity Relationship chemistry.chemical_compound Flavonoid derivatives Drug Discovery Humans Cytotoxic T cell Cytotoxicity Molecular Biology Cell Proliferation Flavonoids Bromine Dose-Response Relationship Drug Molecular Structure 010405 organic chemistry Organic Chemistry 0104 chemical sciences chemistry Halogen Molecular Medicine Drug Screening Assays Antitumor Flavanone |
| Zdroj: | Bioorganic & Medicinal Chemistry Letters. 26:3336-3341 |
| ISSN: | 0960-894X |
| DOI: | 10.1016/j.bmcl.2016.05.038 |
| Popis: | Quantitative relationships between the structure and cytotoxic activity of series flavonoid derivatives were examined. The first regression-based model, developed for 18 flavanone-2-pyrazoline hybrids, involved two interpretable descriptors: a Mor04v and partial atomic charge. The second model, developed for structurally diverse set of compounds, was based on descriptors derived from Hirshfeld surface analysis. This model suggests that cytotoxic activity of compounds can be successfully predicted based on a fraction of H⋯H contacts and a fraction of interactions involving a halogen atom. For non-halogen derivatives, the data reveal that cytotoxic activity is inversely proportional to the percentage of O⋯H and N⋯H close contacts to Hirshfeld surface, while directly proportional to the percentage of H⋯H interactions. Chlorine (1k) and bromine (1l) derivatives of compounds, containing flavanone fused with N-methyl-2-pyrazoline, exhibited high cytotoxic potential against HL-60 cancer cell line (IC50 |
| Databáze: | OpenAIRE |
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