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Öğe Heterocyclic Schiff base derivatives containing pyrazolone moiety: Synthesis, characterization, and in vitro biological studies(Wiley, 2021) Çınar, Ercan; Başaran, Eyüp; Erdoğan, Ömer; Çakmak, Reşit; Boğa, Mehmet; Çevik, ÖzgeIn this study, some pyrazolone-based Schiff base derivatives 2a-e (except 2a)were synthesized for the first time and structurally illuminated by some spec-troscopic techniques (1H,13C NMR, FT-IR) and elemental analysis. Allsynthesized molecules were screened for their anticancer and antioxidantactivities, as well as AChE, BChE, and tyrosinase inhibitory properties.The obtained results exhibited that compounds 1b (IC50= 9.497 Μ) and 2a(IC50= 30.49 Μ) significantly decreased the proliferation of HeLa cells. Onthe other hand, the apoptotic effects of these two compounds were investigatedwith acridine orange/propidium iodide double staining. The apoptotic cellratios of the molecules treated with these two compounds were determined as60 and 64%. Compound 2b (IC50= 17.95 ± 0.47 Μ ) was determined to be avery active substance in the ABTS assay. Compound 2e (A0.5= 43.75± 0.62 M) indicated the closest antioxidant activity to the standard compoundα-TOC (A0.5= 50.58 ± 0.39 M) in the cupric reducing antioxidant capacity(CUPRAC) assay. In inhibition studies of enzymes, it was determined thatcompound 2c had a very active molecule in AChE, BChE, and tyrosinaseinhibitory activities with 82.79 ± 1.03, 91.39 ± 1.06, and 92.60 ± 1.80% inhibi-tion, respectively. It was determined that the target molecules 2a-e showedbetter antioxidant and enzyme inhibitory activities than those of ester deriva-tives 1a-e.Öğe Schiff base derivatives of 4-aminoantipyrine as promising molecules: Synthesis, structural characterization, and biological activities(Pleiades journals, 2022) Çakmak, Reşit; Başaran, Eyüp; Boğa, Mehmet; Erdoğan, Ömer; Çınar, Ercan; Çevik, ÖzgeAbstract: In this study, some Schiff bases derived from 4-aminoantipyrine (4-AAP) (VI–X) were synthesized, characterized by elemental analysis (C, H, N) and three spectral techniques (FT-IR, 1H, and 13C NMR), and then their antioxidant activity was investigated by employing four different methods. Subsequently, the inhibitory influences of the synthesized molecules against acetylcholinesterase (AChE), butyrylcholinesterase (BChE), tyrosinase enzymes were tested. More importantly, the cytotoxic effects of all title molecules were also evaluated on HeLa human cervical cancer and L929 mouse fibroblast cell lines. According to the results obtained, compound (VI) (IC50: 16.82 ± 0.17 μM) showed higher ABTS cation radical scavenging activity than BHA (IC50: 17.59 ± 0.10 μM). In CUPRAC assay, it was determined that the activity ordering of the bioactive molecules has been determined as VII > X > VII > α-TOC > IX > I > II > V > VI. In AChE assay, compound (I) indicated a high potent inhibition activity with 91.75 ± 1.15% better than galanthamine. In BChE assay, compound (VII) had good BChE inhibition activity (78.76 ± 1.47%) better than galanthamine. Compound (V) showed strong tyrosinase inhibition activity with 52.85 ± 0.23% value at 200 μM concentration. Compound (III) showed the best cytotoxic effect on HeLa cells with an IC50 dose of 21.47 µM. Consequently, it can be said that some of these synthesized molecules were potentially new anti-Alzheimer drug candidate molecules.Öğe Synthesis of new fluorinated sulfonates and their Schiff bases as anti-Alzheimer drug candidates: An in vitro-in silico study(Elsevier B.V., 2025) Çakmak, Reşit; Başaran, Eyüp; Ercan, Selami; Boğa, Mehmet; Çınar, Ercan; Topal, GirayIn this research, we designed and synthesized a series of new 3- or 4-(trifluoromethyl)- substituted sulfonate esters (1–14) linked heterocyclic Schiff base derivatives (15–28) as potential inhibitors of acetylcholinesterase and butyrylcholinesterase. The chemical structures of the target compounds were elucidated using elemental analysis and various spectral techniques. In vitro inhibitory results revealed IC50 values ranging from 12.05±0.10 to 43.08±0.20 μM against acetylcholinesterase and 0.42±0.04 to 95.52±0.00 μM against butyrylcholinesterase. Among the tested compounds, most sulfonates were found to inhibit acetylcholinesterase better than butyrylcholinesterase. In contrast, their Schiff base derivatives inhibited butyrylcholinesterase more effectively acetylcholinesterase did. Compounds 19, 20, and 21 inhibited butyrylcholinesterase better than galanthamine. The effects of trifluoromethyl group at positions 3 or 4 of the sulfonate moiety and the biosubstitutions at position R2 of the spacer moiety on the inhibitory activities were evaluated. Moreover, the antioxidant potency of these compounds was assessed by three different assays (DPPH free radical scavenging activity, ABTS cationic radical decolorization, and cupric reducing antioxidant capacity. The newly synthesized derivatives showed very low antioxidant activity (>1000 μM) in the DPPH and ABTS assays, while some of 3- trifluoromethyl substituted Schiff base derivatives (compounds 15, 20, and 21) showed activity closer to α-tocopherol in cupric reducing antioxidant capacity assay. The binding modes and binding free energies for acetylcholinesterase and butyrylcholinesterase inhibitor candidates were determined through docking studies. Taken together, we consider some inhibitor candidates to be valuable lead structures that can be used in further studies to design new anti-Alzheimer's disease drugs. © 2025 Elsevier B.V.Öğe Synthesis of novel N-Acylhydrazones derived from 3,5-dinitrobenzohydrazide and evaluation of their anticholinesterase and antioxidant activities(Pleiades Publishing, 2024) Çakmak, Reşit; Çınar, Ercan; Başaran, Eyüp; Tuneğ, Gülsüm; İzgi, Sevcan; Boǧa, MehmetAbstract: Objective: In this study, it was aimed to determine the antioxidant activities and enzyme inhibition properties of newly synthesized N-acylhydrazone compounds (IIIa–IIIp) bearing an aryl sulfonate moiety. Methods: For this purpose, a series of hydrazone derivatives based on 3,5-dinitrobenzohydrazide (I) was synthesized for the first time and characterized by spectrometric methods (FT-IR, 1H NMR and 13C NMR) and elemental analysis. In vitro anticholinesterase activities of novel hydrazone derivatives were evaluated against acetyl- and butyrylcholinesterase (AChE and BChE) at 200 µM concentration. Moreover, the antioxidant potentials of the same molecules were determined by 2,2′-azino-bis(3-ethylbenzthiazoline-6-sulfonic acid) (ABTS) radical scavenging activity and cupric ion reducing antioxidant capacity (CUPRAC) assays. Results: The obtained results displayed that some of the tested hydrazone compounds had varying enzyme inhibition and antioxidant activities. Discussion: In enzyme inhibition studies, N′-[2-{[4-fluorobenzensulfonyl]oxy}benzylidene]-3,5-dinitrobenzohydrazide (IIIb) with inhibition value 77.13 ± 0.14% showed the closest activity to the standard compound galanthamine with inhibition value 78.14 ± 0.65%. Compared to DPPH and ABTS assays, all of the molecules tested in CUPRAC assay showed antioxidant activities. The molecules tested in CUPRAC assay did not show as much activity as standard molecules (BHA, BHT and α-TOC). Conclusions: Compounds N′-[4-{[4-fluorobenzensulfonyl]oxy}benzylidene]-3,5-dinitrobenzohydrazide (IIIf) and N′-[4-{[4-methoxybenzensulfonyl]oxy}benzylidene]-3,5dinitrobenzohydrazide (IIIh) in this assay were determined to be the most active molecules.Öğe Synthesis, characterization and biological evaluation of esterderivatives of 4-(diethylamino) salicylaldehyde cholinesterase and tyrosinase inhibitors(INESEG Yayıncılık, 2021) Çakmak, Reşit; Çınar, Ercan; Başaran, Eyüp; Boğa, MehmetAlzheimer's disease, one of the diseases that still has no a specific therapy, has become amajor public health issue owing to the increasing population of the elderly, particularly in richcountries. Inhibitory of cholinesterase enzymes (acetylcholinesterase (AChE) and butyrylcholinesterase(BChE), which hydrolyze acetylcholine (ACh) and butyrylcholine (BCh) neurotransmitters, haverecently become a choice for the therapy of this disease. Therefore, there is currently a great demandfor novel enzyme inhibitors with desirable properties for applying in the treatment of AD. In this study,a series of ester derivatives of 4-(diethylamino)salicylaldehyde (1-5) were successfully prepared andstructurally illuminated with FT-IR, 1H- and 13C NMR spectroscopy. The inhibitory properties of thesynthesized molecules on AChE, BChE, and tyrosinase enzymes were investigated, respectively.Compound 1 indicated potent inhibitory activity against BChE with 87.28±0.87% inhibition better thangalanthamine (73.83±0.25 %inhibition) employed as standard. Compound 3 showed significantinhibitory effect against tyrosinase with 87.73±0.22 % inhibition, which is better than kojic acid utilizedas standard. The obtained results clearly revealed that some of these molecules have the potential to be used as potent enzyme inhibitor candidates in the future studies.Öğe Synthesis, spectroscopic, thermal analysis and in vitro cytotoxicity, anticholinesterase and antioxidant activities of new Co(II), Ni(II), Cu(II), Zn(II), and Ru(III) complexes of pyrazolone-based Schiff base ligand(Elsevier B.V., 2023) Çakmak, Reşit; Ay, Burak; Çınar, Ercan; Başaran, Eyüp; Akkoç, Senem; Boğa, Mehmet; Taş, EşrefMetal-based drugs have gained significant importance in medicine in recent years. In this research, a series of new Co(II), Ni (II), Cu (II), Zn(II), and Ru(III) complexes of a Schiff base ligand, (1,5-dimethyl-4-((1-(3-nitrophenyl)ethylidene) amino)-2-phenyl-1,2-dihydro-3H-pyrazol-3-one), were prepared for the first time in excellent yields, and characterized by elemental analysis, FT-IR, 1 H NMR, 13C NMR, ICP-OES, and thermal analysis. The in vitro antiproliferative, anticholinesterase, and antioxidant properties of complexes 1–5 were evaluated. The cytotoxic effects of complexes 1–5 on the viability of colon cancer (DLD-1), breast cancer (MDA-MB-231), and healthy lung (Wl-38) cell lines were investigated using the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide (MTT) method in vitro. The anticancer activities of the ligand and its metal complexes were lower than those of the reference drug, cisplatin. In anticholinesterase activity studies, complex 4 (88.46±0.45% inhibition) in butyrylcholinesterase (BChE) assay showed a higher inhibitory effect than the standard compound galanthamine with 78.14±0.55% inhibition. In antioxidant assays, some complexes showed higher antioxidant activities than standard antioxidant butylated hydroxytoluene (BHT). Among the prepared complexes, complex (4) (IC50=5.91±0.17 µM) in ABTS assay showed the highest antioxidant activity compared to BHT (IC50=16.19 ±0.17 µM). Also, this complex (IC50=10.17±0.36 µM) showed the best antioxidant activity in CUPRAC assay compared to BHT (IC50=39.37±0.12 µM).
