Synthesis and Antimicrobial Activity of Some Novel bis Polyfunctional Pyridine, Pyran, and Thiazole Derivatives

Abstract

In continuation of our efforts to find a new class of antimicrobial agents, treatment of N,N′‐(1,4‐phenylene)bis(2‐cyanoacetamide) (1) with formaldehyde and either benzoylacetonitrile or malononitrile to afford pyridine derivatives 5 and 8, respectively. Similarly, treatment of 1 with different types of aldehydes afforded benzylidene derivatives 9–15, followed by the reaction with rmalononitrile dime to give polyfunctional pyridine derivative 18. Moreover, cyanoacetamide 1 was reacted with chalcone, benzylidenemalononitrile, and 1,3‐diketone to afford pyran derivatives 21, 25, and 28, respectively, followed by the reaction with ammonium acetate to afford polyfunctional pyridine derivatives 22, 26, and 29, respectively. Furthermore, thiazole derivative 32 was prepared via treatment of 1 with elemental sulfur and phenyl isothiocyanate. The newly synthesized compounds were evaluated as antimicrobial activities.

Thiazoles, Their Benzofused Systems, and Thiazolidinone Derivatives: Versatile and Promising Tools to Combat Antibiotic Resistance

“…Recently, a sulfurated analogue of thiazolidinone compounds, the 1,3-thiazolidin-2-thione 76 ( Figure 26 ), was found to act as an antibacterial agent equipotent to chloramphenicol ( 60 ) against S aureus , with a MIC value of 3.12 μg/mL, and with a significant activity also against Bacillus thuringiensis , with a MIC value of 6.25 μg/mL. 133 Despite this interesting activity, thiazole derivative 76 did not demonstrate a significant increase in activity with respect to the pyridine analogue previously reported. Conversely, the authors observed a decrease in the activity against the Gram-negative pathogens was.…”

Synthesis, biological evaluation, and molecular docking studies of novel pyrazole, pyrazoline‐clubbed pyridine as potential antimicrobial agents

“…Pyridine is also an important heterocycle in medicinal chemistry and is associated with several pharmaceutical activities. [ 11–18 ] Figure 1 represents the concept of drug design based on commercially available drugs isoniazid, fezolamine, and dipyrone heterocycles.…”

A retrospect on antimicrobial potential of thiazole scaffold

“…El‐Sayed and Fadda synthesized bispolyfunctional pyridine, pyran and thiazole derivatives from N , N ′‐(1,4‐phenylene)bis(2‐cyanoacetamide). By agar diffusion method, derivatives were tested for antimicrobial effectiveness against St. aureus , B. thuringiensis , E. coli , P. aeruginosa , F. oxysporum and B. fabae in comparison to Chloramphenicol, Cephalothin and Cycloheximide.…”