Synthesis of 4,4-Disubstituted 3-Methylidenechroman-2-ones as Potent Anticancer Agents
| Autor: | Anna Janecka, Tomasz Janecki, Rafal Jakubowski, Marek Mirowski, Tomasz Bartosik, Marek Rozalski, Angelika Długosz, Urszula Krajewska, Dorota K. Pomorska |
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| Rok vydání: | 2017 |
| Předmět: |
Antineoplastic Agents
HL-60 Cells 010402 general chemistry 01 natural sciences Biochemistry Umbilical vein Carboplatin chemistry.chemical_compound Structure-Activity Relationship Isomerism Coumarins Drug Discovery Human Umbilical Vein Endothelial Cells Moiety Structure–activity relationship Humans Phenols General Pharmacology Toxicology and Pharmaceutics Cytotoxicity IC50 Pharmacology 010405 organic chemistry Organic Chemistry Combinatorial chemistry 0104 chemical sciences chemistry Reagent Michael reaction MCF-7 Cells Molecular Medicine |
| Zdroj: | ChemMedChem. 12(8) |
| ISSN: | 1860-7187 |
| Popis: | The synthesis of a new library of 4,4-disubstituted 3-methylidene-3,4-dihydro-2H-chroman-2-ones applying Horner-Wadsworth-Emmons methodology for the construction of an exo-methylidene moiety is reported. Corresponding 3-diethoxyphosphorylchroman-2-ones were synthesized in a three-step reaction sequence consisting of O-methylation of ethyl 2-diethoxyphosphoryl-3-oxoalkanoates, followed by reaction of the obtained 2-diethoxyphosphoryl-3-methoxy-2-alkenoates with phenols or 1-naphthol. The resulting 3-diethoxyphosphorylochromen-2-ones proved to be effective Michael acceptors in reactions with various Grignard reagents. Preliminary biological evaluations showed that many of the synthesized 3-methylidenechroman-2-ones possess very high cytotoxic activity against NALM-6 and HL-60 cancer cell lines (IC50 |
| Databáze: | OpenAIRE |
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