Abstract
New candidates of imidazo[1,2-a]pyridine were designed by combining 2-amino pyridine, TOSMIC and various assorted aldehydes to explore their antioxidant and antifungal potential. The design of these derivatives was based on utilizing the antifungal potential of azoles and TOSMIC moiety. These derivatives were synthesized by adopting multi-component reaction methodology, as it serves as a rapid and efficient tool to target structurally diverse heterocyclic compounds in quantitative yield. The resulting imidazo[1,2-a]pyridine derivatives were structurally verified by 1 HNMR, 13 CNMR, HRMS, and HPLC. The compounds were analyzed for their antioxidant and fluorescent properties and it was observed that compound 15 depicted highest potential. The compounds were evaluated for their antifungal potential to highlight their medical application in the area of Invasive Fungal Infections (IFI). Compound 12 gave the highest antifungal inhibition against Aspergillus fumigatus 3007 and Candida albicans 3018. To elucidate the antifungal mechanism, confocal images of treated fungi were analyzed, which depicted porous nature of fungal membrane. Estimation of fungal membrane sterols by UPLC indicated decrease in ergosterol component of fungal membrane. In silico studies further corroborated with the in vitro results as docking studies depicted interaction of synthesized heterocyclic compounds with amino acids present in the active site of target enzyme (lanosterol 14 alpha demethylase). Absorption, distribution, metabolism, and excretion (ADME) analysis was indicative of drug-likeliness of the synthesized compounds.
Highlights
The importance of heterocyclic compounds is directly associated with the structures that are frequently found in medicines[1]
The compounds were evaluated for their antifungal potential against both Aspergillus fumigatus 3007 & Candida albicans 3018 and it was observed that all the compounds had moderate to significant antifungal effect
The reaction was further screened for different catalyst to optimize the reaction conditions, the experimental results are summarized in Table 1 (Entries 3-10)
Summary
The importance of heterocyclic compounds is directly associated with the structures that are frequently found in medicines[1]. Imidazo[1,2-a]pyridines are one of the most widely used N- heterocyclics and have depicted significant biological activity[4] relevant to medicinal applications. Besides their biological application the core has many applications in electronic devices[5]. These N- heterocyclic often form a complex π- conjugated system and serve as fluorophores[6]. Owing to their robust applications the development of Nitrogen-rich novel heterocyclic compounds is highly desirable
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