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Elsevier4
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8th Black Sea Basin Conference on Analytical Chemistry (8th BBCAC)2
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Anatolian Conference on Synthetic Organic Chemistry ACSOC II2
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11th International Symposium on Pharmaceutical Sciences (ISOPS-11)1
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2nd Cilicia International Symposium On Engineering And Technology (CISET)1
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3rd International Turkish Congress on Molecular Spectroscopy (TURCMOS2017)1
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International Eurasian Conference on Biological and Chemical Sciences (EurasianBioChem 2018)1
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Manisa Celal Bayar Üniversitesi1
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SPRINGER BIRKHAUSER1
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WILEY1
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...
Novel highly functionalized 1,4-naphthoquinone 2-iminothiazole hybrids: Synthesis, photophysical properties, crystal structure, DFT studies, and anti(myco)bacterial/antifungal activity
Gemili, Muge | Nural, Yahya | Ülger, Mahmut | Erat, Selma
In this paper, a series of novel highly functionalized 1,4-naphthoquinone 2-iminothiazole hybrids were synthesized via a cyclization reaction of 2,3-diaminonaphthalene-1,4-dione N-aroylthioureas and alpha-bromoketones in good to excellent yields (74-94%). The stereochemistry of one of the 1,4-naphthoquinone 2-iminothiazole products was characterized by single crystal X-ray diffraction technique. Photophysical properties of the compounds in DMSO, HAc and THF were determined by using UV-vis spectroscopy. The ground state geometries and the absorption spectra of the compounds were also determined using Density Functional Theory (DFT) and time-dependent DFT (TD-DFT) at B3LYP/631 + g(d,p) level of theory. The computed results are consistent with experimental values. An antimicrobial screening w...
Stability constants of cobalt (II) complexes of octahydropyrrolo[3,4-c]pyrrole N-benzoylthiourea derivatives
Gemili, Muge | Nural, Yahya
It is very important to determine the stability constants of complexes, because metals are an integral part of living systems and complexes of many transition metals such as cobalt, platinum, nickel, zinc have an important place in pharmaceutical chemistry. Stability constants of complexes provide information about properties of metals and ligands, such as complex formation requests, coordination and solubility of complex molecules. It is known that aroylthiourea derivatives have been intensively studied in coordination chemistry as bidentate ligands, in analytical chemistry as sensor and in medicinal chemistry as pharmacophore group or intermediate compounds for synthesis of pharmacologically important compounds [1-3]. As a continuation of our previous work [4, in this study, we d...
Acid dissociation constants of 4-aryl-2-(pyrrolidin-1-yl)thiazole derivatives in dimethyl sulfoxide-water hydroorganic solvent”,
Gemili, Muge | Nural, Yahya
Acid dissociation constants (pKa) are among the important parameters having critical significance in the field of pharmacy, chemistry, biology, medicine etc. due to providing information related to acidity, solubility, lipophilicity, bonding to receptors, transport behavior properties of pharmaceutically important molecules, determining the optimum conditions in the development of analytical methods, and understanding the interactions between ligands and metal ions in complexes [1-3]. The thiazole and pyrrolidine scaffolds are intensively studied in drug research, and both of these pharmacophore groups exhibited a wide range of pharmacological activities such as antimicrobial, anticancer activities [3-6]. As a continuation of our previous work [3], in this study, three acid dissoci...
Synthesis and antimycobacterial activity of Co(III) complexes of N-benzoyl-4,6-dioxo-hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carbothioamide derivatives”,
Nural, Yahya | Gemili, Muge | Ersen, Duygu | Ulger, Mahmut | Belveren, Samet | Poyraz, Samet | Serin, Mehmet Sami | Dondas, Haci Ali
S) ligands, play an impotrant role in drug research studies and it has been reported that some of Co(III) complexes show antimycobacterial, antimicrobial, antiviral and other biological activities [1]. Likewise, N-aryl/acyl thiourea derivatives have been intensivelly studied in many chemistry disciplines due to their significant complexation and biological properties [2]. One of the other important classes of drug research studies is heterocyclic compounds containing nitrogen atom as pyrrolidine and its derivatives [3].
Potentiometric Determination of Stability Constants of Co(II), Cu(II), Ni(II) and Zn (II) Complexes of Methyl 5-methyl-4,6-dioxo-2-(5-(2-oxo-2H-chromene-3-carbonyl)-4-phenylthiazol-2-yl)-3,3-diphenyl-octahydro pyrrolo[3,4-c]pyrrole-1-carboxylate
Gemili, Muge | Nural, Yahya
The stability constant parameters have an important place in drug research and development studies. The stability constant provides information to understand the formation and stability of bonds in a complex and to understand the bonding mechanisms, and to determine the concentration of the components present in a mixture in equilibrium [1-3]. In this study, stability constants of Co(II), Cu(II), Ni(II) and Zn(II) complexes of methyl 5-methyl-4,6-dioxo-2-(5-(2-oxo-2H-chromene-3-carbonyl)-4-phenylthiazol 2-yl)-3,3-diphenyl-octahydropyrrolo[3,4-c]pyrrole-1-carboxylate were potentiometrically determined at 25.0 ± 0.1 ºC in a 40% (v/v) DMSO-water mixture. The potentiometrically obtained data were used for the calculation of the stability constants values using the HYPERQUAD comput...
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...
Synthesis and anti(myco)bacterial activity of novel 5,5-diphenylpyrrolidine N-aroylthiourea derivatives and a functionalized hexahydro-1H-pyrrolo[1,2-c]imidazole
Ersen, Duygu | Ulger, Mahmut | Gemili, Muge | Nural, Yahya
In this paper, five novel 5,5-diphenylpyrrolidine N-aroylthiourea derivatives were synthesized by stereoselective cycloaddition of N-diphenylmethylene-protected glycine methyl ester and methyl acrylate, and subsequent coupling with aroylisothiocyanates. The cis-stereochemistry of one of the heterocyclic thiourea derivatives was characterized by single crystal X-ray diffraction studies. The compounds showed antibacterial activity against Staphylococcus aureus, Bacillus subtilis, Aeromonas hydrophila, Escherichia. coli and Acinetobacter baumannii with minimum inhibitory concentration values in the range of 62.5-1000 mu g/mL against these bacterial strains. Antimycobacterial activity of the compounds was investigated against the M. tuberculosis H37Rv strain and all compounds exhibited antimyc...
Acid Dissociation Constants of 5,5-Diphenylpyrrolidine NAroylthioureas and Stability Constants of their Pt(II) and Ni(II) Complexes in Acetonitrile-Water Hydroorganic Solvent
Ersen, Duygu | Gemili, Muge | Nural, Yahya
In this study, acid dissociation constants of 5,5-diphenylpyrrolidine N-aroylthiourea derivatives, exhibiting anti(myco)bacterial activity, were determined by potentiometric titration in 30% (v/v) acetonitrile-water hydroorganic solventat 25 ± 0.1 °C, at an ionic background of 0.1 mol / L of NaCl using the HYPERQUAD computer program. Three acid dissociation constants were determined for each compound 1a-e and we suggest that these acid dissociation constants are related to the carboxyl, enol and enthiol groups. Stability constants of their Pt(II) and Ni(II) complexes were also determined by potentiometric titration under the same conditions stated above using the HYPERQUAD computer program. The ligands behave as bidentate and bind to the metal atom via the S and O atoms. In various p...
Determination of Acid Dissociation Constants (pKa) of Bicyclic Thiohydantoin-Pyrrolidine Compounds in 20% Ethanol-Water Hydroorganic Solvent
Nural, Yahya | Dondas, Haci Ali | Belveren, Samet | Gemili, Muge
The acid dissociation constants of potential bioactive fused ring thiohydantoin- pyrrolidine compounds were determined by potentiometric titration in 20% ( v/ v) ethanol- water mixed at 25 +/- 0.1(0) C, at an ionic background of 0.1 mol/ L of NaCl using the HYPERQUAD computer program. Proton affinities of potential donor atoms of the ligands were calculated by AM1 and PM3 semiempiric methods. We found, potentiometrically, three different acid dissociation constants for 1a- f. We suggest that these acid dissociation constants are related to the carboxyl, enol, and amino groups.