Microwave-Assisted One Pot Three-Component Synthesis of Novel Bioactive Thiazolyl-Pyridazinediones as Potential Antimicrobial Agents against Antibiotic-Resistant Bacteria

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.

Synthetic Derivatives against Wild-Type and Non-Wild-Type Sporothrix brasiliensis: In Vitro and In Silico Analyses

“…Hydrazones are present in different aryl groups which confer antifungal activity [36,37]. Abu-Melha et al [37] performed tests with a one bis aryl hydrazine containing a thiazole ring (Hydrazone 03; Figure 3) against C. albicans.…”

“…Hydrazones are present in different aryl groups which confer antifungal activity [36,37]. Abu-Melha et al [37] performed tests with a one bis aryl hydrazine containing a thiazole ring (Hydrazone 03; Figure 3) against C. albicans. This compound resulted in MICs of 0.18 µg/mL and 3.18 µg/mL against azole-sensitive and azole-resistant C. albicans, respectively [37].…”

“…Abu-Melha et al [37] performed tests with a one bis aryl hydrazine containing a thiazole ring (Hydrazone 03; Figure 3) against C. albicans. This compound resulted in MICs of 0.18 µg/mL and 3.18 µg/mL against azole-sensitive and azole-resistant C. albicans, respectively [37]. Carvalho et al [36] evaluated a series of hydrazones containing the nucleus 7-chloroquinoline.…”

“…The hydrazone shown in Figure 3 (hydrazone 04) stood out with a high percentage of inhibition against C. albicans (71% growth inhibition at a concentration of 12.5 mg/mL). Hydrazones are present in different aryl groups which confer antifungal activity [36,37]. Abu-Melha et al [37] performed tests with a one bis aryl hydrazine containing a thiazole ring (Hydrazone 03; Figure 3) against C. albicans.…”

Synthesis, biological evaluation and induced fit docking simulation study ofd-glucose-conjugated 1H-1,2,3-triazoles having 4H-pyrano[2,3-d]pyrimidine ring as potential agents against bacteria and fungi

“…Firstly, ethyl esters of 2-amino-3-cyano-4-(substituted-phenyl)-4H-pyran-3-carboxylic acids 4a-4s were synthesized via a three-component reaction, including ethyl acetoacetate 1, malononitrile 2 and substituted benzaldehydes 3a-3s (so-called 'multicomponent reaction). [34][35][36][37][38][39][40] An ionic liquid, namely tri-(2-hydroxyethyl)ammonium acetate (THEAA), was used as the catalyst in these reactions under ultrasound-assisted conditions at 25 1C for 20 min. Esters 4a-4s were produced in yields of 88-95% (see ESI, † in the online version of this article for their NMR spectral data).…”