Synthesis, antimicrobial activity and acid dissociation constants of methyl 5,5-diphenyl-1-(thiazol-2-yl)pyrrolidine-2-carboxylate derivatives
Nural, Yahya | Gemili, Muge | Ulger, Mahmut
In this study, a series of polysubstituted methyl 5,5-diphenyl-1-(thiazol-2-yl)pyrrolidine-2-carboxylate derivatives were designed and synthesized by the cyclization reaction of methyl 1-(benzoylcarbamothioyl)-5,5-diphenylpyrrolidine-2-carboxylates and 2-bromo-1-(4-substituted phenyl) ethanones in 70-96% yield. The starting pyrrolidine derivatives were synthesized via a 1,3-dipolar cycloaddition reaction in 83-88% yield. The stereochemistry of one of these methyl 5,5-diphenyl-1-(thiazol-2-yl)pyrrolidine-2-carboxylate derivatives was characterized by a single crystal X-ray diffraction study and the acid dissociation constants of these compounds were determined. An antimicrobial screening was performed against different bacterial and fungal strains and against the M. tuberculosis H37Rv strai...
Synthesis of novel immunomodulatory 1,4-disubstituted bis-1,2,3-triazoles by using click chemistry and their intracellular mechanism of action
Nural, Yahya | Acar, Irem | Yetkin, Derya | Efeoglu, Cagla | Ayaz, Furkan
In this study, six new 1,4-disubstituted bis-1,2,3-triazole compounds, N,N '-(1,2-phenylene)bis(2-(4-R-1H-1,2,3triazol-1-yl)acetamide), were synthesized with high yield (88-96 %) by using click chemistry and their molecular structures were characterized by using NMR, FT-IR, HRMS and elemental analysis techniques. Previous studies suggest anti-inflammatory and analgesic activities for different 1,2,3-triazole derivatives and in the light of those studies we aimed to examine these novel derivatives immunomodulatory activities on the mammalian macrophages. Pro-inflammatory cytokines (TNF, IL6, GMCSF and IL12p40) secretion levels were tested in the presence of bis-1,2,3-triazole compounds when the macrophages were activated with LPS. These new derivatives were able to suppress the product...
New bis-and tetrakis-1, 2, 3-triazole derivatives: Synthesis, DNA cleavage, molecular docking, antimicrobial, antioxidant activity and acid dissociation constants
Nural, Yahya | Ozdemir, Sadin | Yalcin, Mustafa Serkan | Demir, Bunyamin
In this study, a series of bis- and tetrakis-1,2,3-triazole derivatives were synthesized using copper-catalyzed azide-alkyne cycloaddition (CuAAC) click chemistry in 73-95% yield. The bis- and tetrakis-1,2,3-triazoles exhibited significant DNA cleavage activity while the tetrakis-1,2,3-triazole analog 6g completely degraded the plasmid DNA. Molecular docking simulations suggest that compound 6g acts as minor groove binder of DNA by binding through several noncovalent interactions with base pairs. All bis- and tetrakis-1,2,3-triazole derivatives were screened for antibacterial activity against E. coli, B. cereus, S. aureus, P. aeruginosa, E. hirae, L. pneumophila subsp. pneumophila strains and antifungal activity against microfungus C. albicans and C. tropicalis strains. Compound 4d exhibit...
1,4-Naphthoquinone thiazole urea hybrids bearing morpholine/piperazine: synthesis, crystal structure, aldose reductase and α-glycosidase enzyme inhibition, molecular docking, and electrochemical interaction with dsDNA
Efeoglu, Cagla | Nural, Yahya
In this study, new 1,4-naphthoquinone thiazole urea hybrids bearing morpholine (3a-d) or piperazine (3e-h) moiety were synthesized in 76-89 % yields and characterized by 1H NMR, 13C NMR, FT-IR, HRMS, and elemental analysis. The stereochemistry of 3d was determined by single crystal x-ray diffraction study. We evaluated the inhibitory potential of these compounds 3a-h on aldose reductase (ALR2) and alpha-glycosidase enzyme (alpha-GLY) activity. Our results indicate that these compounds substantially inhibit ALR2 at micromolar doses, with inhibition constants (KIs) between 0.79 and 2.20 mu M and inhibit alpha-GLY KI between 0.67 and 2.82 mu M. Molecular docking simulations were utilized to elucidate inhibitory effects and establish structure-activity relationships for the synthesized compoun...