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Öğe Meso carbazole linked Bis-BODIPYs: Design, synthesis, structures and properties(Pergamon-Elsevier Science Ltd, 2023) Aksoy, Burcu Topaloglu; Senocak, Ahmet; Erol, Ismail; Saglam, Mehmet F.; Kandemir, Hakan; Sengul, Ibrahim F.; Cosut, BunyeminIn the present study, BODIPY 4 bearing carbazole ring system at meso position was successfully synthesized as a key building block by the acid-catalyzed condensation reaction of 6-bromo-9-ethyl-9H-carbazole-3-carbaldehyde 3 with 2,4-dimethylpyrrole in one step. The Suzuki and Stille coupling synthetic strategies were subsequently applied to the compound 4 for the construction of a new class of bis-BODIPYs 5 and 6 with extended pi-conjugation by introducing phenyl and bithiophene as linkers between two N-ethylcarbazole units. The structures of novel compounds 4-6 were identified by mass, 1H and 13C NMR spectroscopy along with single crystal X-ray diffraction techniques. The photo-physical features of the targeted BODIPYs were investigated via absorption and fluorescence spectroscopies in solvents with different polarity. Photophysical studies reveal important transitions between carbazole and BODIPYs in solution state, which could be controlled by solvent polarity. Crystal geometry of the molecules and the optical band gaps were supported by DFT calculations. Electrochemical and in situ spectroelectrochemical properties of the synthesized compounds were also investigated to reveal electropolymerizable properties and electrochromic potentials of the targeted materials. The results suggested that the compounds 5 and 6 can be potentially used as useful materials in a range of electrochemical research areas.Öğe Synthesis of furo[2,3-c]carbazoles as potent ?-glucosidase and ?-amylase inhibitors(Taylor & Francis Inc, 2024) Ucar, Tugce N. Uslu; Bingul, Murat; Sahin, Hasan; Kandemir, Hakan; Sengul, Ibrahim F.The carbazole-3-carbaldehyde 2, produced by N-ethyl carbazole via Vilsmeier-Haack reaction, was subjected to Dakin type oxidation with H2O2 and H2SO4 in methanol to produce the carbazole-3-ol 3. The reaction of 3 with a range of commercially available alpha-haloketones 4a-f in the presence of Al2O3 as catalyst in xylene led to their regio-selective cyclization to afford the furo[2,3-c]carbazoles 5a-f. Identification of the furo[2,3-c]carbazoles 5a-f were performed through H-1 NMR,C-13 NMR, FT-IR and high resolution mass spectrometry. Single crystal X-ray diffraction analysis was employed to further confirm the structures of the some of the targeted compounds. In vitro antidiabetic activities of the newly synthesized furocarbazoles 5a-e were investigated utilizing alpha-glucosidase and alpha-amylase enzymes. The biological evaluation revealed the obvious efficiencies of the targeted molecules toward the alpha-glucosidase enzyme inhibition with the potent IC50 values compared to the standard acarbose. In the case of alpha-glucosidase inhibition, the furo[2,3-c]carbazoles chloro substituted 5c and nitro substituted 5f were found to be more potent than acarbose with the values of 215.0 and 162.70 mu M, respectively. On the other hand, the compound 5f was found to be only promising candidate for alpha-amylase enzyme but not as effective as the standard acarbose.Öğe Synthesis of novel benzofuran-4,7-quinones from 4,6-dimethoxybenzofurans specifically targeting breast and lung cancer cells(Springer Wien, 2025) Ucar, Tugce N. Uslu; Izgi, Samet; Demir, Elif Ayazoglu; Uzuner, Selcen Celik; Sengul, Ibrahim F.; Uzuner, Ugur; Kandemir, Hakan4,6-Dimethoxy-2-phenylbenzofurans were synthesized from the one-pot reactions of 3,5-dimethoxyphenol and a range of alpha-bromoacetophenones. The dimethoxybenzofurans were then selectively formylated at C7 using Vilsmeier-Haack method to generate 4,6-dimethoxybenzofuran-7-carbaldehydes which have been effectively converted to 6-dimethoxybenzofuran-4,7-quinones by Dakin oxidation. The cytotoxic potentials of the targeted compounds in MDA-MB-231 breast cancer and A549 lung cancer cell lines were investigated and compared to the cytotoxicity profiles of normal breast and bronchial cells. 2-Phenylbenzofurans mostly targeted lung cancer cells whereas benzofuran-7-carbaldehydes were specifically cytotoxic for metastatic breast cancer cells. The targeted benzofuran derivatives were found to be the most effective compounds for lung and breast cancer. ADME analyses showed lethal doses of all compounds excluding benzofuran-4,7-quinones are around 4000 mg/kg.Öğe Synthesis, biologic properties, and molecular modeling studies of bis-indole based thiosemicarbazones(Springer Wien, 2024) Ceyhan, Sadik M.; Bingul, Murat; Sahin, Hasan; Boga, Mehmet; Saglam, Mehmet F.; Kandemir, Hakan; Sengul, Ibrahim F.The Schiff base condensation reaction of thiosemicarbazides and methylene bridged 2,2 '-bisindolylmethanes, prepared from the acid-catalyzed condensation of 3-aryl-4,6-dimethoxyindole-7-carbaldehydes and formaldehyde, produced a series of the targeted bis-indole based thiosemicarbazones. To explore the biological potential of the newly synthesized compounds, antidiabetic, anticholinesterase, and antioxidant activities were investigated. The structural derivatization carried out by the addition of bromophenyl ring at C3 position of the indole backbone increased the enzyme potency towards the anticholinesterase activity. Some of the targeted compounds showed selective the alpha-glucosidase enzyme inhibition activity. In addition to that, the inhibition concentrations were found to lower that the standard acarbose showing that they may be more efficient agents. Although most of the compounds were effective for the metal chelation capacities (CUPRAC), a couple of examples were found to be favorable for DPPH and ABTS assays. The presence of methyl substituted thiosemicarbazone tail with different indole back bones individually detected as promising targets for ABTS and DPPH activities. The compound methyl substituted thiosemicarbazone was also determined as the most potent agent with the 6 mu M inhibition concentration toward CUPRAC assay. Molecular docking study was performed to support the experimental results.Öğe Synthesis, in vitro and in silico evaluation of indole linked carbohydrazides and 1,3,4-oxadiazoles as new α-glycosidase inhibitors(Elsevier, 2025) Kocaman, Kubra; Bingul, Murat; Ceyhan, Sadik M.; Sahin, Hasan; Saglam, Mehmet F.; Kandemir, Hakan; Sengul, Ibrahim F.The Hemetsberger indole reaction afforded 6-methyl and methoxy substituted indole-2-carboxylates 8 which were then reacted with an excess of hydrazine hydrate in ethanol to produce indole-2-carbohydrazides 9. Treatment of the compounds 9 with a range of commercially available benzoyl chlorides generated new indole linked diacyl hydrazines 10-15 and the corresponding cyclodehydration reaction in the presence of N,N-diisopropylethylamine (DIPEA) and p-toluenesulfonyl chloride (p-TsCl) in acetonitrile gave the targeted indole linked 1,3,4-oxadiazoles 16-21. The antidiabetic properties of the newly synthesized compounds were evaluated by employing alpha-glycosidase and alpha-amylase enzyme inhibition assays and the targeted compounds showed a range of inhibitory activities against alpha-glycosidase and alpha-amylase. The study revealed that the compounds selectively inhibit alpha-glycosidase enzyme. The detection of selective inhibition behaviours for alpha-glycosidase enzyme increased the novelty of the study and most of the IC50 values against the designated enzyme were found to be better than the standard acarbose. The structure-activity relation study illustrated that the oxadiazole ring with the methyl substituted indole and nitro substituted benzene rings demonstrated the best inhibition towards the alpha-glycosidase enzyme. The detected IC50 value for the identified compound 21 was found to be better (>25-fold) than the standard acarbose.
