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Molecules 2015, 20(12), 21924-21938; doi:10.3390/molecules201219809

New 1H-Benzo[f]indazole-4,9-diones Conjugated with C-Protected Amino Acids and Other Derivatives: Synthesis and in Vitro Antiproliferative Evaluation

1
Instituto de Química, Facultad de Ciencias, Pontificia Universidad Católica de Valparaíso, Valparaíso 2373223, Chile
2
Facultad de Farmacia, Universidad de Valparaíso, Valparaíso 2360102, Chile
3
Centro Regional de Estudios en Alimentos y Salud (CREAS), Valparaíso 2362696, Chile
4
Facultad de Farmacia, Departamento de Química Farmacéutica, CIETUS, IBSAL, Universidad de Salamanca, Salamanca 37007, Spain
*
Authors to whom correspondence should be addressed.
Academic Editor: Panayiotis A. Koutentis
Received: 4 November 2015 / Revised: 30 November 2015 / Accepted: 1 December 2015 / Published: 8 December 2015
View Full-Text   |   Download PDF [1275 KB, uploaded 8 December 2015]   |  

Abstract

1H-Benzo[f]indazole-4,9-dione derivatives conjugated with C-protected amino acids (glycine, l-alanine, l-phenylalanine and l-glutamic acid) 6al 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 13C-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. View Full-Text
Keywords: 1,4-naphthoquinone; 1H-benzoindazole; pyrazole; amino acid 1,4-naphthoquinone; 1H-benzoindazole; pyrazole; amino acid
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Molinari, A.; Oliva, A.; Arismendi-Macuer, M.; Guzmán, L.; Fuentealba, M.; Knox, M.; Vinet, R.; San Feliciano, A. New 1H-Benzo[f]indazole-4,9-diones Conjugated with C-Protected Amino Acids and Other Derivatives: Synthesis and in Vitro Antiproliferative Evaluation. Molecules 2015, 20, 21924-21938.

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