Synthesis and in vitro antibacterial evaluation of 6-substituted 4-amino-pyrazolo[3,4-d]pyrimidines

Abstract

Pyrazolo[3,pyrimidines are one of the most important classes of fused heterocyclic compounds which exhibit a broad range of biological and medicinal properties. They are known as anticancer, antifungal, antibacterial, antiviral and anti-inflammatory agents. In this study, some new 6-substituted 4-amino-pyrazolo[3,4-d]pyrimidine derivatives were prepared via reaction of 5-amino-3-methyl-1-phenyl-1H-pyrazole-4-carbonitrile with various nitriles in the presence of sodium ethoxide as catalyst. The inhibitory properties of synthesized compounds were studied according to CLSI guidelines against some pathogenic bacteria including four gram-positive strains (Streptococcus pyogenes, Staphylococcus aureus, Bacillus cereus and Bacillus subtilis subsp. spizizenii) and three gramnegative strains (Pseudomonas aeruginosa, Shigella flexneri and Salmonella enterica subsp. enterica). The antibacterial effects of all derivatives were compared with those of antibiotics belonging to different classes. The values were reported as inhibition zone diameter (IZD), minimum inhibitory concentration (MIC) and minimum bactericidal concentration (MBC). The effect of substituents on the biological activity of derivatives was discussed as well. The inhibitory effect of compound 6a, was shown to be the most, with MIC values in the range of 32-4096 lg/mL. Since most of the synthesized compounds were effective against Streptococcus pyogenes and Pseudomonas aeruginosa, they can be considered as inhibitors of these two bacteria.

Synthesis and evaluation of antimicrobial and antioxidant activity of novel 7‐Aryl‐6H,7H‐ benzo[f]chromeno[4,3‐b]chromen‐6‐one by MgO nanoparticle as green catalyst

“…MIC values were determination by Broth microdilution methods according to CLSI guidelines M07‐A9 and M27‐A2 and MBC and MFC values was applied by Time‐kill test according to CLSI guideline M26‐A …”

Green multicomponent synthesis, antimicrobial and antioxidant evaluation of novel 5-amino-isoxazole-4-carbonitriles

“…Broth microdilution methods according to CLSI guidelines M07-A9 and M27-A2 were used for the determination of MIC values [32, 33]. Bacterial and fungal suspensions at 0.5 McFarland standard were prepared in MHB and SDB, respectively.…”

Synthesis, Characterization and Antimicrobial Evaluation of Novel 6’-Amino-spiro[indeno[1,2-b] quinoxaline[1,3]dithiine]-5’-carbonitrile Derivatives

“…Antimicrobial properties including broth microdilution and time-kill susceptibility were tested based on the IZD, MIC, MBC and MFC values according to the CLSI (the clinical and laboratory standards institute) guidelines M07-A9, M26-A, M02-A11, M44-A and M27-A2. 17,[22][23][24] Gram-negative pathogenic bacteria including Pseudomonas aeruginosa (PTCC 1310), Escherichia coli (PTCC 1399), and Salmonella enterica subsp. enterica (PTCC 1709); Gram-positive strains including Staphylococcus aureus (PTCC 1189) and Staphylococcus epidermidis (PTCC 1435); fungi including Fusarium oxysporum (PTCC 5115) were prepared from the Persian Type Culture Collection (PTCC), Tehran, Iran.…”