Synthesis and Biological Activities of N-(3-Carboxylpropyl)-5-amino-2-hydroxy-3-tridecyl-1,4-benzoquinone and Analogues

Journal of Natural Products
2012.0

Abstract

The synthesis of benzoquinone natural product 2 and three analogues is described. The synthesized compounds were tested for their ability to protect Friedreich's ataxia (FRDA) lymphocytes from induced oxidative stress. One of the analogues (3) conferred cytoprotection in a dose-dependent manner in FRDA lymphocytes at micromolar concentrations. The biological assays suggest that the modification of the 2-hydroxy and N-(3-carboxypropyl) groups in the natural product can improve its antioxidant activity and significantly enhance its ability to protect mitochondrial function under conditions of oxidative stress.

Knowledge Graph

Similar Paper

Synthesis and Biological Activities of N-(3-Carboxylpropyl)-5-amino-2-hydroxy-3-tridecyl-1,4-benzoquinone and Analogues
Journal of Natural Products 2012.0
A Structurally Simplified Analogue of Geldanamycin Exhibits Neuroprotective Activity
ACS Medicinal Chemistry Letters 2013.0
Lipophilic methylene blue analogues enhance mitochondrial function and increase frataxin levels in a cellular model of Friedreich’s ataxia
Bioorganic & Medicinal Chemistry 2018.0
Phenothiazine antioxidants increase mitochondrial biogenesis and frataxin levels in Friedreich's ataxia cells
MedChemComm 2018.0
Lipophilic methylene violet analogues as modulators of mitochondrial function and dysfunction
Bioorganic & Medicinal Chemistry 2017.0
Antioxidant properties of 4-quinolones and structurally related flavones
Bioorganic & Medicinal Chemistry 2012.0
Synthesis of natural product-like polyprenylated phenols and quinones: Evaluation of their neuroprotective activities
Bioorganic & Medicinal Chemistry 2020.0
Synthesis of a natural quinoline alkaloid isolated from the deep-sea-derived fungus and its potential as a therapeutic for Parkinson’s disease
Journal of Asian Natural Products Research 2023.0
N,N-Bis-(8-hydroxyquinoline-5-yl methyl)-benzyl substituted amines (HQNBA): Peroxisome proliferator-activated receptor (PPAR-γ) agonists with neuroprotective properties
Bioorganic & Medicinal Chemistry Letters 2010.0
Toward a Rational Design of Multitarget-Directed Antioxidants: Merging Memoquin and Lipoic Acid Molecular Frameworks
Journal of Medicinal Chemistry 2009.0