Synthesis and antioxidant activity of new lipophilic dihydropyridines
| Autor: | Diego da Costa Cabrera, Heloisa P. Leal, Eduarda Santa-Helena, Dennis Russowsky, Luiz Eduardo Maia Nery, Renata Rodrigues de Moura, Carla Amorim Neves Gonçalves, Marcelo Gonçalves Montes D'Oca |
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| Rok vydání: | 2018 |
| Předmět: |
Dihydropyridines
Antioxidant medicine.medical_treatment DHPS Biochemistry Antioxidants chemistry.chemical_compound Structure-Activity Relationship Nitrendipine Nifedipine Picrates Drug Discovery medicine Sulfamic acid Butylated hydroxytoluene Organic chemistry Benzothiazoles Molecular Biology Dose-Response Relationship Drug Molecular Structure Vitamin E Organic Chemistry Biphenyl Compounds chemistry Nitro Sulfonic Acids Hydrophobic and Hydrophilic Interactions medicine.drug |
| Zdroj: | Bioorganic chemistry. 84 |
| ISSN: | 1090-2120 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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