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Title: Synthesis of Amino Acid–Naphthoquinones and In Vitro Studies on Cervical and Breast Cell Lines
Authors: Rivera Avalos, Ernesto
De Loera, Denisse
Araujo Huitrado, Jorge Gustavo
Escalante García, Ismailia Leilani
Muñoz Sánchez, Miguel Antonio
Hernández López, Hiram
López, Jesús Adrian
López, Lluvia
Issue Date: Nov-2019
Publisher: MDPI
Abstract: We performed an extensive analysis about the reaction conditions of the 1,4-Michael addition of amino acids to 1,4-naphthoquinone and substitution to 2,3-dichloronaphthoquinone, and a complete evaluation of stoichiometry, use of different bases, and the pH influence was performed. We were able to show that microwave-assisted synthesis is the best method for the synthesis of naphthoquinone–amino acid and chloride–naphthoquinone–amino acid derivatives with 79–91% and 78–91% yields, respectively. The cyclic voltammetry profiles showed that both series of naphthoquinone–amino acid derivatives mainly display one quasi-reversible redox reaction process. Interestingly, it was shown that naphthoquinone derivatives possess a selective antitumorigenic activity against cervix cancer cell lines and chloride–naphthoquinone–amino acid derivatives against breast cancer cell lines. Furthermore, the newly synthetized compounds with asparagine–naphthoquinones (3e and 4e) inhibited ~85% of SiHa cell proliferation. These results show promising compounds for specific cervical and breast cancer treatment
ISSN: 1420-3049
Other Identifiers: info:eu-repo/semantics/publishedVersion
Appears in Collections:*Documentos Académicos*-- M. en Ciencias y Tecnología Química

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