Design and synthesis of 2-quinolones as antioxidants and antimicrobials: a rational approach

Abstract

As an important class of compounds, 2-quinolones are isomeric to 4-quinolones and isosteric to coumarins. The compounds that have 2-quinolone moiety are associated with interesting biologic activities such as antibacterial, anticancer, antiviral, cardiotonic, and N-methyl-D-aspartate receptor inhibitor functions, among others. In the current study, based on the rational approach, lead molecules of the 2-quinolone skeleton were designed for binding to the bacterial DNA gyrase subunit A. Docking simulations and quantitative structure activity relationship (QSAR) analysis were performed using the Molegro Virtual Docker and Sarchitech softwares. Based on these studies, the 7-amino-4-methylquinolin-2(1H)-one parent compound and its carboxamides (JST 1-15) were synthesized using Conrad Limpach synthesis. The synthesized test compounds then were characterized by thin-layer chromatography and melting point determination, as well as by ultraviolet, infrared (IR), 1 H-NMR, and MS studies. All synthesized and purified compounds were tested for antioxidant and antibacterial activity.

Synthesis, characterization and biological activity of some new carbostyril bearing 1H-pyrazole moiety

“…Carbostyril (2-quinolone) ring system represents an important class of compounds not only for their theoretical interest but also for their antimicrobial (Jayashree et al, 2010;Creaven et al, 2010), antiproliferative (Chen et al, 2007), antithrombotic (Buchanan et al, 1989), antihepatitis B (Cheng et al, 2008), anti-HIV (Zhang et al, 2003), antitumor (Joseph et al, 2002), antioxidative activity (Chung and Woo, 2001) and cytotoxicity against human tumor cell lines (He et al, 2005). Several carbostyril derivatives are also nitric oxide production inhibitors (Ito et al, 2004), 5-HT 1B /5-HT 2A receptor antagonists (McCort et al, 2001), Rho-kinase inhibitors (Letellier et al, 2008), androgen receptor (Oeveren et al, 2007), p38aMAP kinase inhibitors (Peifer et al, 2008) and induce mitochondrial dysfunction (Chilin et al, 2005).…”

Synthesis, characterization, and antimicrobial evaluation of carbostyril derivatives of 1H-pyrazole

“…The carbostyril (2-quinolone) skeleton is a fertile source of biologically important molecules possessing a wide spectrum of biological and pharmacological activities, such as antimicrobial (Jayashree et al, 2009;Creaven et al, 2010), antiproliferative (Chen et al, 2007), antithrombotic (Buchanan et al, 1989), anti-hepatitis B (Cheng et al, 2008), anti-HIV (Zhang et al, 2003), anti-tumor (Joseph et al, 2002), antioxidative activity (Chung and Woo, 2001) and cytotoxicity against human tumor cell lines (He et al, 2005). Several carbostyril derivatives are also nitric oxide production inhibitors (Ito et al, 2004), 5-HT 1B /5-HT 2A receptor antagonists (McCort et al, 2001), Rho-kinase inhibitors (Letellier et al, 2008), androgen receptors (Oeveren et al, 2007), p38aMAP kinase inhibitors (Peifer et al, 2008) and induce mitochondrial dysfunction (Chilin et al, 2005).…”

The simple synthesis and antimicrobial activity of novel fluoroquinolone derivatives from natural amino acid salts

“…Due to such a wide range of applicability in medicine, bioorganic chemistry, as well as synthetic organic chemistry, there has been increasing interests in the development of new quinolone and fluoroquinolone derivatives to enrich this domain (Sakineh et al, 2009;Murugesan et al, 2008;Chai et al, 2009). Structureactivity relationship studies discovered that N1, C2-H, C3-carboxylic acid, C4-carbonyl, C6-F, and C7-piperazine are essential or beneficial for antibacterial activity (Najma et al, 2009;Jayashree et al, 2009;Patel and Patel 2009). As part of our ongoing interests to find new fluoroquinolone derivatives, we have focused our attention on introducing natural amino acid piece to the fluoroquinolone ring at N1-position.…”