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Antiproliferative Benzoindazolequinones as Potential Cyclooxygenase-2 Inhibitors

Instituto de Química, Facultad de Ciencias, Pontificia Universidad Católica de Valparaíso, Valparaíso 2373223, Chile
Centro de Bioinformática y Biología Integrativa, Facultad de Ciencias de la Vida, Universidad Nacional Andrés Bello, Santiago 8370146, Chile
Laboratorio de Farmacología, Centro de Micro Bioinnovación, Facultad de Farmacia, Universidad de Valparaíso, Valparaíso 2360102, Chile
Centro Regional de Estudios en Alimentos Saludables (CREAS), Valparaíso 2362696, Chile
Departamento de Ciencias Farmacéuticas-Química Farmacéutica, Facultad de Farmacia, CIETUS, IBSAL, Universidad de Salamanca, 37007 Salamanca, Spain
Author to whom correspondence should be addressed.
Academic Editors: David Díez and María Ángeles Castro
Molecules 2019, 24(12), 2261;
Received: 22 May 2019 / Revised: 6 June 2019 / Accepted: 15 June 2019 / Published: 18 June 2019
(This article belongs to the Special Issue Application of Organic Synthesis to Bioactive Compounds)
Quinones and nitrogen heterocyclic moieties have been recognized as important pharmacophores in the development of antitumor agents. This study aimed to establish whether there was any correlation between the in silico predicted parameters and the in vitro antiproliferative activity of a family of benzoindazolequinones (BIZQs), and to evaluate overexpressed proteins in human cancer cells as potential biomolecular targets of these compounds. For this purpose, this study was carried out using KATO-III and MCF-7 cell lines as in vitro models. Docking results showed that these BIZQs present better binding energies (ΔGbin) values for cyclooxygenase-2 (COX-2) than for other cancer-related proteins. The predicted ∆Gbin values of these BIZQs, classified in three series, positively correlated with IC50 measured in both cell lines (KATO-III: 0.72, 0.41, and 0.90; MCF-7: 0.79, 0.55, and 0.87 for Series I, II, and III, respectively). The results also indicated that compounds 2a, 2c, 6g, and 6k are the most prominent BIZQs, because they showed better IC50 and ∆Gbin values than the other derivatives. In silico drug absorption, distribution, metabolism, and excretion (ADME) properties of the three series were also analyzed and showed that several BIZQs could be selected as potential candidates for cancer pre-clinical assays. View Full-Text
Keywords: 1H-benzo[f]indazole-4,9-diones; benzoindazolequinones; antiproliferative activity; COX-2 inhibitors; docking 1H-benzo[f]indazole-4,9-diones; benzoindazolequinones; antiproliferative activity; COX-2 inhibitors; docking
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MDPI and ACS Style

Molinari, A.; Oliva, A.; Arismendi-Macuer, M.; Guzmán, L.; Acevedo, W.; Aguayo, D.; Vinet, R.; San Feliciano, A. Antiproliferative Benzoindazolequinones as Potential Cyclooxygenase-2 Inhibitors. Molecules 2019, 24, 2261.

AMA Style

Molinari A, Oliva A, Arismendi-Macuer M, Guzmán L, Acevedo W, Aguayo D, Vinet R, San Feliciano A. Antiproliferative Benzoindazolequinones as Potential Cyclooxygenase-2 Inhibitors. Molecules. 2019; 24(12):2261.

Chicago/Turabian Style

Molinari, Aurora, Alfonso Oliva, Marlene Arismendi-Macuer, Leda Guzmán, Waldo Acevedo, Daniel Aguayo, Raúl Vinet, and Arturo San Feliciano. 2019. "Antiproliferative Benzoindazolequinones as Potential Cyclooxygenase-2 Inhibitors" Molecules 24, no. 12: 2261.

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