Bülent Alıcı

2-Imidazoline– and 1,4,5,6-tetrahydropyrimidine–ruthenium(II) complexes and catalytic synthesis of furan

Abstract The complexes RuCl 2 (L 1 )(arene) ( 3–4 ) (L1=H CNCH 2 CH 2 N R, R=Et, arene= p -MeC 6 H 4 CHMe 2 or C 6 Me 6 ) and RuCl 2 (L 2 )(arene) ( 5–6 ) (L 2 =H CNCH 2 CH 2 CH 2 N R, R=Me, Ph, CH 2 Ph, p -MeC 6 H 4 ) have been synthesized by reaction of [RuCl 2 (arene)] 2 with 1-alkyl-2-imidazoline ( 1 ) or 1-alkyl-1,4,5,6-tetrahydropyrimidine ( 2 ). In each of these complexes ( 3–6 ) the ligand is bound via the imine (NC) nitrogen atom. The new complexes are capable of catalyzing the activation of ( Z )-3-methylpent-2-en-4-yn-1-ol into 2,3-dimethylfuran in very good yield, via intramolecular cyclization, and the 1,4,5,6-tetrahydropyrimidine complexes 5 and 6 appeared to be the best catalyst precursors. Cyclic voltammetry shows that the nature of the arene ligand, rather than that of the nitrogen containing ligand, controls the electron-richness of the complexes.

Synthesis, characterization and antimicrobial activities of novel silver(I) complexes with coumarin substituted N-heterocyclic carbene ligands.

Eight new coumarin substituted silver(I) N-heterocyclic carbene (NHC) complexes were synthesized by the interaction of the corresponding imidazolium or benzimidazolium chlorides and Ag2O in dichloromethane at room temperature. Structures of these complexes were established on the basis of elemental analysis, (1)H NMR, (13)C NMR, IR and mass spectroscopic techniques. The antimicrobial activities of carbene precursors and silver NHC complexes were tested against standard strains: Enterococcus faecalis, Staphylococcus aureus, Escherichia coli, Pseudomonas aeruginosa and the fungi Candida albicans and Candida tropicalis. Results showed that all the compounds inhibited the growth of the all bacteria and fungi strains and some complexes performed good activities against different microorganisms. Among all the compounds, the most lipophilic complex bis[1-(4-methylene-6,8-dimethyl-2H-chromen-2-one)-3-(naphthalene-2-ylmethyl)benzimidazol-2-ylidene]silver(I) dichloro argentate (5e) was found out as the most active one.

Synthesis and carbonic anhydrase inhibitory properties of novel coumarin derivatives

A newly series of water-soluble 1-alkyl-3-(4-methyl-7, 8-dihydroxy-2H-chromen-2-one) benzimidazolium chloride salts (3a-j) were synthesized and their inhibitory effects on the activity of purified human carbonic anhydrase (hCA) I and II were evaluated. hCA I and II from human erythrocytes were purified by a simple one step procedure by using Sepharose 4B-L-tyrosine-sulphanilamide affinity column. The result showed that all the synthesized compounds were inhibited the CA isoenzymes activity. Among them, 3g and 3j were found to be most active (IC50 = 22.09 µM and 20.33 µM) for hCA I and hCA II, respectively.

Synthesis and characterization of N-substituted 1,4,5,6-tetrahydropyrimidine containing functional polymers as SO2 and CO2 sorbents

Novel vinyl monomers containing 1,4,5,6-tetrahydropyrimidine were prepared by the reaction of N-substituted-1,3-diaminopropane with N,N-dimethyl-formamide dimethylacetal, which gave 1-alkyl or aryl substituted 1,4,5,6-tetrahydropyrimidines, Alkylation of the tetrahydropyrimidine derivatives by chloromethylstyrene produces the N-methyl-N′-vinyl benzyl-1,4,5,6-tetrahydropyrimidinium chloride in high yields. These monomers were readily polymerized in dimethylformamide by AIBN at 80°C. Homopolymers and soluble linear copolymers were prepared and copolymerization parameters were rationalized. Further, insoluble terpolymers prepared from these monomers, styrene and divinylbenzene were tested for the sorption of the weakly acidic gases gave excellent results.

Coumarin or benzoxazinone based novel carbonic anhydrase inhibitors: synthesis, molecular docking and anticonvulsant studies

Abstract Among many others, coumarin derivatives are known to show human carbonic anhydrase (hCA) inhibitory activity. Since hCA inhibition is one of the underlying mechanisms that account for the activities of some antiepileptic drugs (AEDs), hCA inhibitors are expected to have anti-seizure properties. There are also several studies reporting compounds with an imidazole and/or benzimidazole moiety which exert these pharmacological properties. In this study, we prepared fifteen novel coumarin-bearing imidazolium and benzimidazolium chloride, nine novel benzoxazinone-bearing imidazolium and benzimidazolium chloride derivatives and evaluated their hCA inhibitory activities and along with fourteen previously synthesized derivatives we scanned their anticonvulsant effects. As all compounds inhibited purified hCA isoforms I and II, some of them also proved protective against Maximal electroshock seizure (MES) and ScMet induced seizures in mice. Molecular docking studies with selected coumarin derivatives have revealed that these compounds bind to the active pocket of the enzyme in a similar fashion to that previously described for coumarin derivatives.

Synthesis and catalytic properties of arene complexes of ruthenium(II) prepared from Si, Zr, Ti and Al alkoxides by the sol-gel process

Methods of synthesizing materials for catalysis were developed by synthesizing eta;-arene complexes of ruthenium(ii) coordinated to vinylpyridine that was followed by sol-gel polymerization with 3-methacryloxypropyltriethoxysilane. To enforce sufficient catalytic properties, a series of hybrid materials from Si, Zr, Ti and Al alkoxides were prepared by co-condensation. The hydrolysis and polycondensation of materials were performed at different experimental conditions. The monomeric compounds were identified and catalytic activities were tested for cyclization of (Z)-3-methylpent-2-en-4-yn-1-ol to 2,3-dimethylfuran.

Synthesis, characterization and tyrosinase inhibitory properties of benzimidazole derivatives

Abstract1-Alkylbenzimidazole and 1,3-dialkyl benzimidazolium salts were synthesized and characterized by the data of IR, 1H NMR, 13C NMR spectra and elemental analyses. These compounds were investigated as tyrosinase inhibitors. Tyrosinase has been purified from banana by affinity chromatography on a Sepharose 4B gel conjugated with L-tyrosine-p-aminobenzoic acid. All the synthesized compounds inhibited the tyrosinase activity. Among the compounds studied, 1,4-di(1H-benzo[d]imidazol-1-yl)butane was found to be the most active tyrosinase inhibitor (IC50 0.31 mM).

New coumarin derivatives as carbonic anhydrase inhibitors

Abstract In the current study, a series of 4-chloromethyl-7-hydroxy-coumarin derivatives containing imidazolium, benzimidazolium, bisbenzimidazolium and quaternary ammonium salts were synthesized, characterized and the inhibition effects of the derivatives on human carbonic anhydrases (hCA I and hCA II) were investigated as in vitro. Structures of these coumarins were confirmed by FT-IR, (1)H NMR, (13)C NMR and LC–MS analyses. Structure activity relationship study showed that 3d (IC50: 79 μM for hCA I and 88 μM for hCA II) performed higher inhibitory activity than others.

Synthesis and radical polymerization of novel vinyl monomers having the imidazoline and pyrimidine moiety

SummaryAlkylation of the methylene bridged tetrahydropyrimidine derivatives by chloromethylstyrene produces the bridged bis(4-vinylbenzyl)-1,4,5,6,-tetrahydropyrimidinium salts in high yields. Similar procedures are used to prepare 2-imidazolinium derivatives. The quaternary salts which support functional side groups of potential biomedical interest are characterized by means of spectroscopic methods. These monomers are readily polymerized free radically in solution of dimethyl formamide at moderate temperatures. The soluble and insoluble polymers containing 2-imidazolinium and 1,4,5,6-tetrahydropyrimidinium salts were found to exhibit antibacterial activites againstEscherichia coli.

Functionalized imidazolium and benzimidazolium salts as paraoxonase 1 inhibitors: Synthesis, characterization and molecular docking studies

Paraoxonase (PON) is a key enzyme in metabolism of living organisms and decreased activity of PON1 was acknowledged as a risk for atherosclerosis and organophosphate toxicity. The present study describes the synthesis, characterization, PON1 inhibitory properties and molecular docking studies of functionalized imidazolium and benzimidazolium salts (1a-5g). The structures of all compounds were elucidated by IR, NMR, elemental analysis and structures of compounds 2b and 2c were characterized by single-crystal X-ray diffraction. Compound 1c, a coumarin substituted imidazolium salt showed the best inhibitory effect on the activity of PON1 with good IC50 value (6.37 μM). Kinetic investigation was evaluated for this compound and results showed that this compound is competitive inhibitor of PON1 with Ki value of 2.39 μM. Molecular docking studies were also performed for most active compound 1c and one of least active compound 2c in order to determine the probable binding model into active site of PON1 and validation of the experimental results.