Synthesis and antioxidant activity of new lipophilic dihydropyridines.

Autor: da Costa Cabrera D; Kolbe Laboratory of Organic Synthesis, School of Chemistry and Food, Federal University of Rio Grande-FURG, Rio Grande, RS, Brazil., Santa-Helena E; Institute of Biological Sciences, Federal University of Rio Grande-FURG, Rio Grande, RS, Brazil., Leal HP; Kolbe Laboratory of Organic Synthesis, School of Chemistry and Food, Federal University of Rio Grande-FURG, Rio Grande, RS, Brazil., de Moura RR; Kolbe Laboratory of Organic Synthesis, School of Chemistry and Food, Federal University of Rio Grande-FURG, Rio Grande, RS, Brazil., Nery LEM; Institute of Biological Sciences, Federal University of Rio Grande-FURG, Rio Grande, RS, Brazil., Gonçalves CAN; Institute of Biological Sciences, Federal University of Rio Grande-FURG, Rio Grande, RS, Brazil., Russowsky D; Laboratory of Organic Synthesis, Institute of Chemistry, Federal University of Rio Grande do Sul, Porto Alegre, RS, Brazil., Montes D'Oca MG; Kolbe Laboratory of Organic Synthesis, School of Chemistry and Food, Federal University of Rio Grande-FURG, Rio Grande, RS, Brazil. Electronic address: dqmdoca@furg.br.
Jazyk: angličtina
Zdroj: Bioorganic chemistry [Bioorg Chem] 2019 Mar; Vol. 84, pp. 1-16. Date of Electronic Publication: 2018 Nov 13.
DOI: 10.1016/j.bioorg.2018.11.009
Abstrakt: Dihydropyridines (DHPs) obtained from Hantzsch multicomponent reactions are an important pharmaceutical class of compounds marketed as antihypertensive (e.g., nifedipine, nitrendipine, and amlodipine) drugs. This study synthesized new symmetrical and unsymmetrical long-chain fatty DHPs using multicomponent reactions under metal-free conditions with sulfamic acid as a catalyst. The DHPs were tested for antioxidant activity using three different methods. The insertion of a long chain into the DHP core contributed to antioxidant potential, and compounds derived from nitro aldehydes have better antioxidant potential than the antihypertensive drug nifedipine. In addition, fatty analogs to nifedipine derived from palmitic and oleic chains showed similar antioxidant activity to the common standards butylated hydroxytoluene and vitamin E. These results showed that our new synthesized products may find novel applications as antioxidant additives or for tools for use in drug discovery.
(Copyright © 2018 Elsevier Inc. All rights reserved.)
Databáze: MEDLINE
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