Characterization of Antimicrobial, Antioxidant, and Leishmanicidal Activities of Schiff Base Derivatives of 4-Aminoantipyrine

Teran, Rommy; Guevara, Rommel; Mora, Jessica; Dobronski, Lizeth; Barreiro-Costa, Olalla; Beske, Timo; Pérez-Barrera, Jorge; Araya-Maturana, Ramiro; Rojas-Silva, Patricio; Poveda, Ana; Heredia-Moya, Jorge

doi:10.3390/molecules24152696

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Characterization of Antimicrobial, Antioxidant, and Leishmanicidal Activities of Schiff Base Derivatives of 4-Aminoantipyrine

by Rommy Teran^1,†,

Rommel Guevara

^1,2,†,

Jessica Mora

¹,

Lizeth Dobronski

³,

Olalla Barreiro-Costa

^3,4,

Timo Beske

^2,5, Jorge Pérez-Barrera^1,2,

Ramiro Araya-Maturana

⁶

Patricio Rojas-Silva

^3,4,

Ana Poveda

^1,2,*

and

Jorge Heredia-Moya

^3,4,*

Facultad de Ciencias Químicas, Universidad Central del Ecuador, Quito 170521, Ecuador

Instituto de Investigación en Salud Pública y Zoonosis-CIZ, Universidad Central del Ecuador, Quito 170521, Ecuador

Centro de Investigación Traslacional, Universidad De Las Américas, Quito 170503, Ecuador

⁴

Centro de Investigación Biomédica (CENBIO), Facultad de Ciencias de la Salud Eugenio Espejo, Universidad UTE, Quito 170527, Ecuador

⁵

Facultad de Medicina Veterinaria, Universidad Central del Ecuador, Quito 170521, Ecuador

⁶

Instituto de Química de Recursos Naturales, Programa de Investigación Asociativa en Cáncer Gástrico (PIA-CG), Universidad de Talca, Talca 3460000, Chile

Authors to whom correspondence should be addressed.

^†

These authors contributed equally to this work.

Molecules 2019, 24(15), 2696; https://doi.org/10.3390/molecules24152696

Received: 26 March 2019 / Revised: 8 April 2019 / Accepted: 8 April 2019 / Published: 24 July 2019

(This article belongs to the Special Issue New Studies on the Synthesis of Biologically Active Products)

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Abstract

Our main interest is the characterization of compounds to support the development of alternatives to currently marketed drugs that are losing effectiveness due to the development of resistance. Schiff bases are promising biologically interesting compounds having a wide range of pharmaceutical properties, including anti-inflammatory, antipyretic, and antimicrobial activities, among others. In this work, we have synthesized 12 Schiff base derivatives of 4-aminoantipyrine. In vitro antimicrobial, antioxidant, and cytotoxicity properties are analyzed, as well as in silico predictive adsorption, distribution, metabolism, and excretion (ADME) and bioactivity scores. Results identify two potential Schiff bases: one effective against E. faecalis and the other with antioxidant activity. Both have reasonable ADME scores and provides a scaffold for developing more effective compounds in the future. Initial studies are usually limited to laboratory in vitro approaches, and following these initial studies, much research is needed before a drug can reach the clinic. Nevertheless, these laboratory approaches are mandatory and constitute a first filter to discriminate among potential drug candidates and chemical compounds that should be discarded. View Full-Text

Keywords: schiff base synthesis; Leishmania; antimicrobial activity; cytotoxicity

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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

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MDPI and ACS Style

Teran, R.; Guevara, R.; Mora, J.; Dobronski, L.; Barreiro-Costa, O.; Beske, T.; Pérez-Barrera, J.; Araya-Maturana, R.; Rojas-Silva, P.; Poveda, A.; Heredia-Moya, J. Characterization of Antimicrobial, Antioxidant, and Leishmanicidal Activities of Schiff Base Derivatives of 4-Aminoantipyrine. Molecules 2019, 24, 2696. https://doi.org/10.3390/molecules24152696

AMA Style

Teran R, Guevara R, Mora J, Dobronski L, Barreiro-Costa O, Beske T, Pérez-Barrera J, Araya-Maturana R, Rojas-Silva P, Poveda A, Heredia-Moya J. Characterization of Antimicrobial, Antioxidant, and Leishmanicidal Activities of Schiff Base Derivatives of 4-Aminoantipyrine. Molecules. 2019; 24(15):2696. https://doi.org/10.3390/molecules24152696

Chicago/Turabian Style

Teran, Rommy, Rommel Guevara, Jessica Mora, Lizeth Dobronski, Olalla Barreiro-Costa, Timo Beske, Jorge Pérez-Barrera, Ramiro Araya-Maturana, Patricio Rojas-Silva, Ana Poveda, and Jorge Heredia-Moya. 2019. "Characterization of Antimicrobial, Antioxidant, and Leishmanicidal Activities of Schiff Base Derivatives of 4-Aminoantipyrine" Molecules 24, no. 15: 2696. https://doi.org/10.3390/molecules24152696

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