Easy and rapid preparation of benzoylhydrazides and their diazene derivatives as inhibitors of 15-lipoxygenase
| Autor: | Carolina Mascayano, Macarena Rojas-Poblete, Pablo Dahech, Williams Acevedo-Fuentes, Claudia Torrent, Pablo Barrias, Cristian Tirapegui |
|---|---|
| Rok vydání: | 2017 |
| Předmět: |
0301 basic medicine
Phenylhydrazines Clinical Biochemistry Pharmaceutical Science Chemistry Techniques Synthetic Imides Benzoates 01 natural sciences Biochemistry Antioxidants Structure-Activity Relationship 03 medical and health sciences chemistry.chemical_compound Lipoxygenase Non-competitive inhibition Drug Discovery Arachidonate 15-Lipoxygenase Humans Organic chemistry Lipoxygenase Inhibitors Imide Molecular Biology Benzoic acid biology 010405 organic chemistry Chemistry Organic Chemistry Active site Combinatorial chemistry 0104 chemical sciences Molecular Docking Simulation Hydrazines 030104 developmental biology Docking (molecular) Lipophilicity biology.protein Molecular Medicine Soybeans Oxidation-Reduction |
| Zdroj: | Bioorganic & Medicinal Chemistry Letters. 27:1649-1653 |
| ISSN: | 0960-894X |
| Popis: | Two series of diaza derivatives were prepared by solvent-free condensation of benzoic acid and 4-substituted phenylhydrazines in order to obtain phenylhydrazides (HYD series) and, by oxidation of these compounds, the corresponding benzoyldiazenes (DIA series). Both sets were evaluated as inhibitors of soybean 15-lipoxygenase activity and antioxidant capability in the FRAP and CUPRAC assays. The most potent inhibitors of both series exhibited IC50 values in the low micromolar range. Kinetic studies showed that at least the more active compounds were competitive inhibitors. Docking results indicated that the most potent inhibitor interacts strongly with Ile-839 and iron in the active site. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|
Full Text from ScienceDirect