Microwave‐assisted rapid and efficient synthesis of chromene‐fused pyrrole derivatives through multicomponent reaction and evaluation of antibacterial activity with molecular docking investigation

Abstract

The current study aimed to identify a new strategy of FeCl 3 catalyzed multicomponent synthesis of substituted 2H-chromene-fused pyrrole derivatives.A series of chromene-based pyrrole prepared by employing an array of 3-nitro-2H-chromenes, aniline, and acetylacetone in toluene under microwave irradiation. Using FeCl 3 as a prompt catalyst and microwave irradiation to synthesize 2H-chromene-fused pyrrole motifs significantly reduces the reaction time and facilitates to high yields (83%-95%). Structure of all synthesized compounds analyzed by spectroscopic analysis. One-pot reaction, short reaction period, and simple experimental procedure are the fascinating properties associated with this protocol. The in vitro antibacterial activity of the entire series was assessed against Staphylococcus aureus and Escherichia coli. Out of all the compounds, 15b and 15h revealed most excellent potency against both the bacterial strains relative to the reference gentamicin. Docking study was employed to determine the possible binding orientation of DNA gyrase with the active sites of chromene-fused pyrrole analog. The docking results show that compounds 15b and 15h have higher binding affinity with energy −8.00 and −8.80 kcal/mol. These results illuminate the mode of binding progression and provide an esteemed pathway for the design and the structural modification of chromene-fused pyrroles as a newly advanced class of antibacterial agent.

Nostocine A Derivatives as Human DNA Topoisomerase II-alpha Inhibitor

“…Furthermore, the docking study was carried out by using AutoDock Tools 4.2. for ligand-receptor interaction with visualization by Discovery Studio R2 2017 and analyzed by PyMOL program. 11,12…”

Green and Efficient Construction of Chromeno[3,4-c]pyrrole Core via Barton–Zard Reaction from 3-Nitro-2H-chromenes and Ethyl Isocyanoacetate

“…The chromenopyrrole moiety is present in a wide range of natural and synthetic compounds with a number of important useful properties [ 1 , 2 , 3 , 4 , 5 , 6 , 7 , 8 , 9 , 10 , 11 , 12 , 13 , 14 , 15 ]. Thus, chromeno[3,4- b ]pyrrole scaffold is the basis of the skeleton of type I lamellarin alkaloids isolated from marine mollusks, tunicates and sponges [ 1 , 2 ] ( Figure 1 ).…”

Síntese, caracterização e avaliação antimicrobiana de 1,2,4-oxadiazóis derivados do ácido trans-3,4-(metilenodioxi)-cinâmico

“…Several biological functions, such as anticancer, (Maftei, et al, 2013;Kumar et al, 2011;Moniot et al, 2017), antiinflammatory (Bezerra et al, 2005;Gobec et al, 2015;Bora et al, 2014), anticonvulsant (Mohammadi-Khanaposhtani et al, 2016, antibacterial (Baral et al, 2019), antifungal (Sortino et al, 2008), antiviral (Chernyshov et al, 2022), antioxidant Gobec et al, 2015), analgesic (Farooqui et al, 2009), antiinsomnia (Brotschi et al, 2019), antiparasitic (Haugwitz et al, 1985), antidepressant, anti-edema, and anti-Alzheimer (Biernacki et al, 2020) activity have been attributed to compounds with the 1,2,4-oxadiazole ring. Additionally, 1,2,4-oxadiazoles exhibit pesticidal activity, such as insecticidal (Liu et al, 2017), antifungal (Yang et al, 2021), and herbicidal activity (Ölmez & Waseer, 2020).…”