1. Synthesis and antioxidant activity of new lipophilic dihydropyridines.
- Author
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da Costa Cabrera D, Santa-Helena E, Leal HP, de Moura RR, Nery LEM, Gonçalves CAN, Russowsky D, and Montes D'Oca MG
- Subjects
- Antioxidants chemical synthesis, Antioxidants chemistry, Dihydropyridines chemical synthesis, Dihydropyridines chemistry, Dose-Response Relationship, Drug, Hydrophobic and Hydrophilic Interactions, Molecular Structure, Structure-Activity Relationship, Antioxidants pharmacology, Benzothiazoles antagonists & inhibitors, Biphenyl Compounds antagonists & inhibitors, Dihydropyridines pharmacology, Picrates antagonists & inhibitors, Sulfonic Acids antagonists & inhibitors
- Abstract
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.)
- Published
- 2019
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