Synthesis, antibacterial, anti-oxidant and molecular docking studies of imidazoquinolines

Abstract

Quinoline and imidazole derivatives have been playing a significant role in functional bioactivities and were potentially used as antibacterial, antifungal, anticancer, and anti-inflammatory drugs. Owing to the limitation of drug resistance, herein we synthesized thio-, chloro-, and hydroxyl-functionalized various imidazoquinolines by molecular hybridization approach. All the imidazoquinoline derivatives were examined for their antibacterial activity against selected bacterial pathogens by the agar well diffusion method. In addition, the anti-oxidant efficacy of imidazoquinolines was also tested using ferric reducing antioxidant power (FRAP). Among them, electron-withdrawing (-Cl) substituent containing imidazoquinoline 5f showed higher antibacterial and antioxidant activities than other imidazoquinolines and reached the effectiveness of the standard. In addition, compounds 4f, 5e, and 3f showed moderate antibacterial activity and other derivatives displayed weak activity against various pathogens. Molecular docking studies were also performed on selected imidazoquinoline derivatives (3f, 4f, and 5f), which showed high docking score and strong binding energy values. These results revealed that thio-imidazoquinoline could assist as a prototype for the designing of multidrug-resistant antibiotics against various microbial organisms.

Zeolite (Y‐H)‐based green synthesis, antimicrobial activity, and molecular docking studies of imidazole bearing oxydibenzene hybrid molecules

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Synthesis of novel conjugated benzofuran-triazine derivatives: Antimicrobial and in-silico molecular docking studies

“…In this method, it is claimed that the pharmacophores used in the structure of the compounds can be a powerful center for biological activity. There are many studies in which hybridization is used to strengthen the biological effect of two pharmacophores possessing the same biological effects [ 4 , 5 ]. Many of the presented biologically active hybrid molecules are under different phases of clinical trials [ [6] , [7] , [8] ].…”

New quinoline-based triazole hybrid analogs as effective inhibitors of α-amylase and α-glucosidase: Preparation, in vitro evaluation, and molecular docking along with in silico studies

“…Quinoline scaffolds find application in numerous pharmaceutically potent drugs and received much attention in the field of medicinal chemistry. Quinoline scaffolds were reported to show a broad range of biological activities such as antifungal ( Tabassum et al, 2021 ), antibacterial ( Ghosh et al, 2020 ), antileishmanial ( Gupta et al, 2021 ), anticonvulsant ( Al-Ostoot et al, 2021 ), anti-Zaka virus ( Taha et al, 2019 ), antimalarial ( Vinindwa et al, 2021 ), proton pump inhibitors ( Cernicchi et al, 2021 ), antiproliferative ( Ammar et al, 2021 ), antiulcer ( Atukuri et al, 2020 ), antidiabetic ( Taha et al, 2019 ), antimicrobial, anti-inflammatory ( Douadi et al, 2020 ), antitrypanosomal ( Zhang et al, 2018 ), antitubercular ( Nesaragi et al, 2021 ), antioxidant agent ( Velmurugan et al, 2021 ), and antihypertensive ( Kumari et al, 2019 ).…”