Abstract
A new series of quinoline derivatives 5–12 were efficiently synthesized via one-pot multicomponent reaction (MCR) of resorcinol, aromatic aldehydes, β-ketoesters, and aliphatic/aromatic amines under solvent-free conditions. All products were obtained in excellent yields, pure at low-cost processing, and short time. The structures of all compounds were characterized by means of spectral and elemental analyses. In addition, all the synthesized compounds 5–12 were in vitro screened for their antioxidant and antibacterial activity. Moreover, in silico molecular docking studies of the new quinoline derivatives with the target enzymes, human NAD (P)H dehydrogenase (quinone 1) and DNA gyrase, were achieved to endorse their binding affinities and to understand ligand–enzyme possible intermolecular interactions. Compound 9 displayed promising antioxidant and antibacterial activity, as well as it was found to have the highest negative binding energy of -9.1 and -9.3 kcal/mol for human NAD (P)H dehydrogenase (quinone 1) and DNA gyrase, respectively. Further, it complied with the Lipinski’s rule of five, Veber, and Ghose. Therefore, the quinoline analogue 9 could be promising chemical scaffold for the development of future drug candidates as antioxidant and antibacterial agents.
Highlights
Quinolines are very important compounds used for new drug development
A new series of quinoline derivatives 5–12 were efficiently synthesized via one-pot multicomponent reaction (MCR) of resorcinol, aromatic aldehydes, β-ketoesters, and aliphatic/aromatic amines under solvent-free conditions
The present study entails the synthesis of a novel series of quinoline analogues 5–12 via one-pot multicomponent reaction (MCR) under solvent-free conditions
Summary
Quinolines are very important compounds used for new drug development. They are reported as highly selective cytotoxic (Luo et al, 2009; Bawa et al, 2010; Meshram et al, 2012; Sidoryk et al., 2015), broad-spectrum antimicrobial (including activity against Mycobacterium tuberculosis as well as HIV-1 integrase inhibition activity) (Wang et al, 2019), antileishmanial (Asif, 2014), anticonvulsant, anti-inflammatory, cardiovascular activity (Acharyulu et al, 2008; Kumar, Bawa, and Gupta, 2010), and have antidiabetic effect (Shang, et al, 2018a). Synthetic manipulations have to be made to minimize the use of hazardous chemicals by replacing the traditional organic solvents in reactions and their subsequent workup with other nontoxic and environmentally benign solvents such as water. For complementing this way and in continuation of our search work Toxicity (ADME/T) properties of the newly synthesized compounds were calculated
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