Abstract
Pyridazine and thiazole derivatives have various biological activities such as antimicrobial, analgesic, anticancer, anticonvulsant, antitubercular and other anticipated biological properties. Chitosan can be used as heterogeneous phase transfer basic biocatalyst in heterocyclic syntheses. Novel 1-thiazolyl-pyridazinedione derivatives were prepared via multicomponent synthesis under microwave irradiation as ecofriendly energy source and using the eco-friendly naturally occurring chitosan basic catalyst with high/efficient yields and short reaction time. All the prepared compounds were fully characterized by spectroscopic methods, and their in vitro biological activities were investigated. The obtained results were compared with those of standard antibacterial/antifungal agents. DFT calculations and molecular docking studies were used to investigate the electronic properties and molecular interactions with specific microbial receptors.
Highlights
In recent years, a substantial number of pyridazine derivatives containing different moieties and/or substituents have demonstrated anti-inflammatory/analgesic, antipyretics, antiplatelet, anticancer, antidiabetic, antihypertensive, antidepressant/anxiolytic, anticonvulsant, antifungal, antibacterial, antitubercular, anti-bronchial asthma, antiallergic and other anticipated biological properties [1,2,3,4,5,6,7,8]
In continuation of our previously reported works on the synthesis of new biologically active agents [31,32,33,34,35,36,37], we present an efficient synthesis of novel 1-thiazolyl-pyridazinedione derivatives as antimicrobial agents, which have not been reported hitherto in a multicomponent synthesis under microwave irradiation (MWI) as an ecofriendly energy source and using the eco-friendly naturally occurring chitosan catalyst
The minimum inhibitory concentration (MIC) of the tested compounds on cell metabolism/viability of S. aureus, P. aeruginosa and C. albicans was determined using XTT assay compared to the standard counterparts
Summary
A substantial number of pyridazine derivatives containing different moieties and/or substituents have demonstrated anti-inflammatory/analgesic, antipyretics, antiplatelet, anticancer, antidiabetic, antihypertensive, antidepressant/anxiolytic, anticonvulsant, antifungal, antibacterial, antitubercular, anti-bronchial asthma, antiallergic and other anticipated biological properties [1,2,3,4,5,6,7,8]. Thiazoles are considered an important class of heterocyclic compounds, found in many potent biologically active molecules such as sulfathiazole (an antimicrobial drug), Ritonavir (an antiretroviral drug), Abafungin (an antifungal drug) and Tiazofurin (an antineoplastic drug). Over the years, it has been noticed that interesting biological activities [9,10] were associated with thiazole derivatives. The utility of MCRs under microwave irradiation (MWI) in the synthesis of heterocyclic compounds enhanced reaction rates and improved regioselectivity [21,22,23,24]
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