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, crystal structure, DFT studies, acid dissociation constant, and antimicrobial activity of methyl 2-(4-chlorophenyl)-7a-((4-chlorophenyl)carbamothioyl)-1-oxo-5,5-diphenyl-3-thioxo-hexahydro-1H-pyrrolo[1,2-e]imidazole-6-carboxylate
Nural, Yahya | Gemili, Muge | Ulger, Mahmut
A novel bicyclic thiohydantoin fused to pyrrolidine compound, methyl 2-(4-chlorophenyl)-7a-((4-chlorophenyl)carbamothioyl)-1-oxo-5,5-diphenyl-3-thioxo-hexahydro-1H-pyrrolo[1,2-e]imidazole-6-carboxylate, was synthesized by the cyclization reaction of dimethyl 5,5-diphenylpyrrolidine-2,4-dicarboxylate and 4-chlorophenyl isothiocyanate in the presence of 4-(dimethylamino)pyridine to form methyl 2-(4-chlorophenyl)-1-oxo-5,5-diphenyl-3-thioxo-hexahydro-1H-pyrrolo[1,2-e]imidazole-6-carboxylate with concomitant addition reaction of the 4-chlorophenyl isothiocyanate in 79% yield. The structural characterization was performed by NMR, FT-IR, MS and HRMS techniques, and the stereochemistry of the compound was determined by single crystal X-ray diffraction study. In addition, the molecular structure a...
Synthesis, biological properties, and acid dissociation constant of novel naphthoquinone–triazole hybrids.
Nural, Yahya | Ozdemir, Sadin | Demir, Bunyamin | Yalcin, Mustafa Serkan | Erat, Selma
A series of novel 1,4-naphthoquinone-triazole hybrids, N-(3-amino-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-2-(4-R-1H-1,2,3-triazol-1-yl)acetamide, was synthesized by click chemistry in the presence of sodium ascorbate and copper(II) sulfate pentahydrate in 81-94% yield. Various biological properties of the synthesized compounds including DNA binding/cleavage, antioxidant, antibacterial and antifungal properties were evaluated. The DNA binding study was performed using dsDNA and G-quadruplex DNA. All of the compounds showed fluorescence increase in the presence of DNA, regardless of the structure. Up to 2.9 and 2.5 times fluorescence increase upon incubation with double stranded or G-quadruplex DNA was detected for 5f and 5g, respectively. The docking studies performed on dsDNA and G-quadruple...
Synthesis, anti-inflammatory activity, inverse molecular docking, and acid dissociation constants of new naphthoquinone-thiazole hybrids
Efeoglu, Cagla | Selcuk, Ozge | Celik, Begum | Tumkaya, Ece | Nural, Yahya
hronic Inflammation is associated with various types of diseases that involves pro-inflammatory cytokines like IL-6 and TNF-alpha. High costs and serious side effects of available anti-inflammatory/immunomodulatory drugs led us to design new compounds with promising anti-inflammatory activities. Many drugs and biologically important compounds involve naphthoquinone and thiazole moieties in their core structures. Thereby, here we report the synthesis, characterization and anti-inflammatory activities of new naphthoquinone thiazole hybrids by reaction of naphthoquinone acyl thioureas with various alpha-bromoketone derivatives. The position of NO2 group in one of the phenyl rings of naphthoquinone thiazole hybrids was changed while different substituents were introduced at the para position o...
Pt(II) and Ni(II) complexes of octahydropyrrolo[3,4-c]pyrrole N-benzoylthiourea derivatives: Synthesis, characterization, physical parameters and biological activity
Gemili, Muge | Ulger, Mahmut | Nural, Yahya
In this study, four novel Pt(II) and Ni(II) complexes of octahydropyrrolo[3,4-c]pyrrole, consisting of pyrrolidine fused to pyrrolidine-2,5-dione, N-benzoylthiourea derivatives were synthesized and their structural characterization was performed by NMR, FT-IR, MS, HRMS and elemental analysis techniques and single crystal X-ray diffraction studies. The octahydropyrrolo[3,4-c]pyrrole N-benzoylthiourea compound 3c crystallizes triclinic, with space group P-1. Pt(II) and Ni(II) ions created cis-complexes Pt(II) 4c and Ni (II) 5a forming distorted square-planar structures in orthorhombic space groups Pnma and Pbca, respectively. Furthermore, the ligands behave as bidentate and bind to the metal atom via the S and O atoms. Acid dissociation constants of the ligands were determined by potentiomet...
Anti-inflammatory Potential of 1,4-Naphthoquinone Acyl Thiourea Hybrids on Lipopolysaccharide-Activated Mammalian Macrophages, and Their Acid Dissociation Constants
Canatar, Ceren | Türkben, Havva | Efeoglu, Cagla | Karasu, Elize | Nural, Yahya | Ayaz, Furkan
In this study, seven new and known 1,4-naphthoquinone acyl thiourea hybrids were synthesized and their molecular structures were confirmed by various analytical methods. These derivatives were tested for their anti-inflammatory potential on the murine macrophages. Pro-inflammatory cytokine production levels and cell viabilities were compared between the groups and with LPS positive control groups to determine the most potent anti-inflammatory drug candidate. Our results suggest that these derivatives had anti-inflammatory activity without exerting major cytotoxicity. Their future evaluation in inflammatory and autoimmune disease settings will be crucial for their possible utilization in the clinical setting. The acid dissociation constants of synthesized hybrids 1-7 were determined potenti...