New 1H-Benzo[f]indazole-4,9-diones Conjugated with C-Protected Amino Acids and Other Derivatives: Synthesis and in Vitro Antiproliferative Evaluation
| Autor: | Marcela Knox, Leda Guzmán, Arturo San Feliciano, Alfonso Oliva, Mauricio Fuentealba, Aurora Molinari, Marlene Arismendi-Macuer, Raúl Vinet |
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| Jazyk: | angličtina |
| Rok vydání: | 2015 |
| Předmět: |
Indazoles
Stereochemistry Substituent Pharmaceutical Science Antineoplastic Agents Breast Neoplasms 1 4-Naphthoquinone Pyrazole Conjugated system In Vitro Techniques Article Analytical Chemistry lcsh:QD241-441 chemistry.chemical_compound Structure-Activity Relationship lcsh:Organic chemistry Stomach Neoplasms Drug Discovery Tumor Cells Cultured Structure–activity relationship Humans Physical and Theoretical Chemistry Amino Acids Cell Proliferation chemistry.chemical_classification Indazole 1H-benzoindazole Molecular Structure Organic Chemistry Condensation reaction Amino acid pyrazole 1 4-naphthoquinone chemistry amino acid Chemistry (miscellaneous) Molecular Medicine Female Drug Screening Assays Antitumor |
| Zdroj: | Molecules, Vol 20, Iss 12, Pp 21924-21938 (2015) Molecules Volume 20 Issue 12 Pages 21924-21938 Molecules; Volume 20; Issue 12; Pages: 21924-21938 |
| ISSN: | 1420-3049 |
| Popis: | 1H-Benzo[f]indazole-4,9-dione derivatives conjugated with C-protected amino acids (glycine, l-alanine, l-phenylalanine and l-glutamic acid) 6a-l were prepared by chemically modifying the prenyl substituent of 3-methyl-7-(4-methylpent-3-enyl)-1H-benzo[f]indazole-4,9-dione 2 through epoxidation, degradative oxidation, oxidation and N-acyl condensation reactions. The chemical structures of the synthesized compounds were elucidated by analyzing their IR, ¹H-NMR and (13)C-NMR spectral data together with elemental analysis for carbon, hydrogen and nitrogen. The preliminary in vitro antiproliferative activity of the synthesized derivatives was evaluated on KATO-III and MCF-7 cell lines using a cell proliferation assay. The majority of the derivatives exhibited significant antiproliferative activity with IC50 values ranging from 25.5 to 432.5 μM. These results suggest that 1H-benzo[f]indazole-4,9-dione derivatives are promising molecules to be researched for developing new anticancer agents. |
| Databáze: | OpenAIRE |
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