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- ArticleAçık Erişim2024Exploring new 5-Nitroimidazole Derivatives as Potent Acetylcholinesterase and Butyrylcholinesterase Enzyme Inhibitors
Gursoy, Sule; Satici, Doruk; Kuzu, Burak; Turkmenoglu, Burcin; Dilek, Esra; Algul, Oztekin
Discovering new compounds capable of inhibiting physiologically and metabolically significant drug targets or enzymes is of paramount importance in biological chemistry. With this aim, new 5-nitroimidazole derivatives (1–4) were designed and synthesized, and their inhibitory activities against acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) were discovered using acetyl (butyryl) thiocholine and Ellman's reagents for spectrophotometric assay. The inhibitory profiles of the synthesized compounds were assessed by comparing their IC50 and Ki values. Results demonstrate significant inhibitory activity of all synthesized compounds against both AChE and BuChE compared to the reference compound, donepezil. Notably, compound 4 exhibited dual inhibition of these enzymes, showing the highest activity against Electrophorus electricus AChE (EeAChE) with a Ki value of 0.024±0.009 nM and against equine BuChE (eqBuChE) with a Ki value of 0.087±0.017 nM. Furthermore, molecular modeling was conducted to study the interaction modes of the most potent compound (4) and donepezil in the active site of their related enzymes’ crystal structures (PDB ID: 4EY7 and 4BDS, respectively). Additionally, drug-likeness, ADME, and toxicity profiles of the compounds and metronidazole were predicted. The above results indicated that the dual inhibition of these enzymes is considered as a promising strategy for the treatment of neurological disorder especially Alzheimer's disease.
RDL Kalıcı Kaydıİncele - ArticleAçık Erişim2023New Fluoro- and Trifluoromethyl-Substituted Trimethoxychalcones as Anticancer Agents: Synthesis, Bio-evaluation, and Computational Studies
Polat, M. Fatih; Anil, Derya Aktas; Ozkemahli, Gizem; Turkmenoglu, Burcin; Hepokur, Ceylan; Burmaoglu, Serdar; Algul, Oztekin
We designed and synthesized a novel series of trimethoxy chalcones with CF3 or F substituents at various positions of ring B, characterized using IR, NMR spectral data, and elemental analyses, based on the fact that methoxy and fluoro-substituted chalcones are included in the literature as a pharmacophore due to their anticancer activities. All compounds (12-21) were tested for cytotoxicity against A549, HEPG2, MCF7, and normal mouse fibroblasts (L929) using the XTT assay. The most active compound, 13, was also shown to induce MCF7 cell cycle arrest at the G0/G1 phase, indicating that they exert their antitumor potency via MCF7 cell apoptosis. The mechanisms involved in apoptotic cell death induced by compound 13 were also investigated to see if apoptotic proteins such as Bax, Bcl-2, and p53 were involved. In addition, the compounds with the strongest apoptotic effects against human EGFR and VEGFR-2 receptors were studied in silico. Finally, methoxy and fluoro-substituted chalcones derivatives have been shown to have potent anticancer properties.
RDL Kalıcı Kaydıİncele - ArticleYalnız künye2023N-(benzazol-2-yl)-2-substituted phenylacetamide derivatives: Design, synthesis and biological evaluation against MCF7 breast cancer cell line
Zoatier, Bayan; Yildirim, Metin; Alagoz, Mehmet Abdullah; Yetkin, Derya; Turkmenoglu, Burcin; Burmaoglu, Serdar; Algul, Oztekin
This work describes the straightforward and efficient one-pot synthesis of a new library of N-(benzazol-2-yl)-2-substituted phenylacetamide derivatives (19–27). Using the MTT assay, these compounds were evaluated for their in vitro anticancer activity against the MCF7 human breast cancer cell line, and the results were compared to the standard doxorubicin. The majority of compounds exhibited an inhibitory effect against the cancer cell line, with compounds 19, 22, and 26 exhibiting exceptional cytotoxicity against MCF7 cells. Using flow cytometry, the most potent compound 19 on the induction of apoptosis in the breast cancer cell line was determined. Compound 19 induced G1-phase cell cycle arrest followed by apoptotic cell death. In silico analyses of potent compounds 19, 22, and 26 were conducted to investigate their interactions with Human DNA topoisomerase II. The energy calculations were found to be in excellent agreement with the calculated IC50 values. In addition, drug similarity parameter values for the three active compounds were determined using in silico ADME prediction studies. Considering all of these results, it appears that these N-(benzazol-2-yl)-2-substituted phenylacetamide derivatives may be effective anticancer agents. This work may possibly generate new concepts for the enhancement of inhibitors of human DNA topoisomerase II for breast cancer treatment.
RDL Kalıcı Kaydıİncele - ArticleYalnız künye2023Machine learning study: from the toxicity studies to tetrahydrocannabinol effects on Parkinson's disease
Yucel, Mehmet Ali; Ozcelik, Ibrahim; Algul, Oztekin
Aim: Investigating molecules having toxicity and chemical similarity to find hit molecules. Methods: The machine learning (ML) model was developed to predict the arylhydrocarbon receptor activity of anti-Parkinson's and US FDA-approved drugs. The ML algorithm was a support vector machine, and the dataset was Tox21. Results: The ML model predicted apomorphine in anti-Parkinson's drugs and 73 molecules in FDA-approved drugs as active. The authors were curious if there is any molecule like apomorphine in these 73 molecules. A fingerprint similarity analysis of these molecules was conducted and found tetrahydrocannabinol (THC). Molecular docking studies of THC for dopamine receptor 1 (affinity = -8.2 kcal/mol) were performed. Conclusion: THC may affect dopamine receptors directly and could be useful for Parkinson's disease.
RDL Kalıcı Kaydıİncele - ArticleAçık Erişim2023Novel oxalamide derivatives for COXs expression and breast cancer: design, synthesis, biological evaluation, and docking studies
Kuzu, Burak; Hepokur, Ceylan; Algul, Oztekin
In the present study, new oxalamide-based compounds were designed from thalidomide and synthesized easily and with high yields (from 69% up to 93%) by a two-step method. The antiproliferative effects of synthesized 6a-d and 7a-d compounds on (ER+) MCF-7 and (ER-) MDA-MB-231 breast cancer cell line and human fibroblast WI-38 healthy cell line were investigated by the MTT method. The results showed that compound 7d was the most potent candidate against both MCF-7 and MDA-MB-231 cell lines with IC50 = 4.72 μM and 6.37 μM, respectively. To investigate whether antiproliferative effect of the compounds on breast cancer cell lines is dependent on COXs, expressions of COX-1/2 on the MCF-7 cell line were investigated by the Western-Blot technique. Among synthesized compounds, compound 7d increased the expression of both COX-1 and COX-2. The inhibition potential of compounds on COX-1/2 enzymes was investigated by molecular docking compared to inhibitor co-ligand celecoxib in crystal structures of COX-1 (PDB ID: 3KK6) and COX-2 (PDB ID: 3LN1). Docking results indeed showed that compound 7d had a higher binding affinity for both COX-1 and COX-2 active sites. Consequently, the novel oxalamide-based compounds presented here may be important candidate molecules for the development of new COX-dependent antiproliferative agents.
RDL Kalıcı Kaydıİncele - ArticleAçık Erişim2022Synthesis, molecular docking and some metabolic enzyme inhibition properties of biphenyl-substituted chalcone derivatives
Burmaoglu, Serdar; Kazancioglu, Elif Akin; Kazancioglu, Mustafa Z.; Sağlamtaş, Rüya; Yalcin, Gozde; Gulcin, Ilhami; Algul, Oztekin
The new synthesized biphenyl-substituted chalcone derivatives were evaluated against the human carbonic anhydrase isoenzymes I and II (hCA I and hCA II), acetylcholinesterase (AChE), and butyrylcholinesterase (BChE) enzymes. The synthesized biphenyl-substituted chalcone derivatives showed Ki values in range of 14.71–62.95 nM against hCA I, 31.69–47.20 nM against hCA II, 4.33–16.97 nM against AChE, and 3.72–6.74 nM against BChE enzymes. The synthesized biphenyl-substituted chalcone derivatives exhibited effective inhibition profiles against indicated metabolic enzymes when compared to acetazolamide (for hCA I and II) and tacrine (for AChE and BChE). Molecular docking, MD simulation, and MM/PB(GB)SA calculations were applied for nine compounds. The best dock scores were obtained from compounds 21, 22 and 24, and the lowest △GMM/PBSA energy were determined as 19, 21 and 22. All results may contribute to the development of new drugs particularly to treat some disorders, which widespread display in the world including glaucoma and Alzheimer's diseases.
RDL Kalıcı Kaydıİncele - ArticleYalnız künye2022Synthesis, Biological Evaluation and In Silico Studies of Some 2-Substituted Benzoxazole Derivatives as Potential Anticancer Agents to Breast Cancer
Kuzu, Burak; Hepokur, Ceylan; Alagoz, Mehmet Abdullah; Burmaoglu, Serdar; Algul, Oztekin
In an attempt to develop potent and selective anticancer agents, some 5- or 6- and N-substituted benzoxazol-2-carboxamide derivatives were designed, synthesized, and evaluated for their cyclooxygenase inhibitory, antioxidant, and anti-proliferative activity against MCF-7 and MDA-MB-231 cell lines. Among them 5-OMe, N-piperidine substituted (compound 30), 5-OMe, N-4-methylpiperidine substituted (compound 31) and 5-Cl, N-piperidine substituted (compound 34) benzoxazole 2-carboxamide compounds have a moderate inhibitory effect in COX-1 and COX-2 enzymes. Anti-proliferative studies show that compound 30 (IC50=5.35 μM) and compound 31 (IC50=5.82 μM) have similar activity to reference drug 5-FU (IC50=3.95 μM) on MCF-7 cell but they have lower toxic effect for healthy WI-38 cell line. For the MCF-7 cell line, compounds 30 and 31 show approximately 1.5 times higher selectivity compared to the 5-FU control. Among the synthesized compounds 30, 31, and 34 had the best anti-proliferative effect and were used to perform flow cytometry and cell cycle analysis on MCF-7 cell line. To predict the binding modes and pharmacokinetic parameters of all compounds, in silico studies were carried out. These compounds may shed light on cancer treatment and cancer research.
RDL Kalıcı Kaydıİncele - ArticleYalnız künye2022Design, synthesis and in vitro antiproliferation activity of some 2-aryl and -heteroaryl benzoxazole derivatives
Kuzu, Burak; Hepokur, Ceylan; Turkmenoglu, Burcin; Burmaoglu, Serdar; Algul, Oztekin
Background: Phortress produces reactive electrophilic metabolites that form DNA adducts only in sensitive tumor cells. The authors converted the 2-phenylbenzothiazole nucleus in phortress to 2-aryl and -heteroaryl benzoxazole derivatives (11 new and 14 resynthesized). All synthesized compounds were studied for antitumor activity in various cancer cells. Materials & methods: Cytotoxicity, cell morphology, flow cytometry and cell-cycle analyses of compounds were performed and more active derivatives were tested in the MCF-7 cell line. Conclusion: Methyl 2-(thiophen-2-yl)benzo[d]oxazole-6-carboxylate (BK89) has a higher effect than fluorouracil to induce apoptotic cell death (apoptosis value of 49.44%). Cell-cycle analysis shows that the compounds BK89 and methyl 2-(furan-2-yl)benzo[d]oxazole-6-carboxylate (BK82) can be used as potential cell-cycle blockers by arresting MCF-7 cells in G0/G1 phase at rates of 63% and 85%, respectively. Plain language summary There is an urgent need to develop potent and selective anticancer agents. In this study, the design and applications of compounds sensitive to specific cancer cells and targeting cancer cells were investigated. The results show that the synthesized compounds can be antiproliferative drug candidates for breast cancer. These compounds may shed light on cancer treatment and cancer research.
RDL Kalıcı Kaydıİncele - ArticleAçık Erişim20222-Phenyl substituted Benzimidazole derivatives: Design, synthesis, and evaluation of their antiproliferative and antimicrobial activities
Ersan, Ronak Haj; Kuzu, Burak; Yetkin, Derya; Alagoz, Mehmet Abdullah; Dogen, Aylin; Burmaoglu, Serdar; Algul, Oztekin
The inability to meet the desired outcomes of anticancer treatment and decrease in treatment success of bacterial and fungal infections accelerated research in these areas. Our research group has conducted numerous studies, especially on benzimidazole ring systems’ antiproliferative and antimicrobial activities. In this study, the antiproliferative activity of benzimidazole compounds was tested against A549, A498, HeLa, A375, and HepG2 cancer cell lines by MTT assay. All compounds exhibited good to potent antiproliferative activity against all tested cancer cell lines. Compounds 6-chloro-2-(4-fluorobenzyl)-1H-benzo[d]imidazole (30) and 6-chloro-2-phenethyl-1H-benzo[d]imidazole (46) were especially active against HeLa and A375 cancer cell lines with IC50 values in the range of 0.02–0.04 µM. In contrast, compounds 6-chloro-2-((p-tolyloxy)methyl)-1H-benzo[d]imidazole (67) and 5(6)-chloro-2-((4-hydroxyphenoxy)methyl)-1H-benzimidazole (68) were active against A549 and A498 cancer cell lines with an IC50 value of 0.08 µM. These compounds (30, 46, 67, and 68) were less toxic to normal human cells than the positive control compound methotrexate, which was screened to determine its toxicity against normal cell lines (HEK293). In the second part of the study, all compounds were tested to demonstrate their antimicrobial properties. All compounds exhibited moderate activity against all tested bacteria and fungi. However, some phenoxy methyl derivatives 5-chloro-2-((4-chlorophenoxy)methyl)-1H-benzo[d]imidazole (69) and 5,6-dichloro-2-((4-chlorophenoxy)methyl)-1H-benzo[d]imidazole and (74) were most active against Candida (<3.90 µg/mL). Molecular docking studies were carried out against certain proteins in order to identify potential targets of the antiproliferative effects of the synthesized compounds. The docking scores of the compounds were found to be significantly compatible with the antiproliferative activity results. [Figure not available: see fulltext.]
RDL Kalıcı Kaydıİncele - ArticleAçık Erişim2022Exploring enzyme inhibition profiles of novel halogenated chalcone derivatives on some metabolic enzymes: Synthesis, characterization and molecular modeling studies
Anil, Derya Aktas; Polat, M. Fatih; Saglamtas, Ruya; Tarikogullari, Ayse H.; Alagoz, M. Abdullah; Gulcin, Ilhami; Algul, Oztekin; Burmaoglu, Serdar
Enzyme inhibition is a very active area of research in drug design and development. Chalcone derivatives have a broad enzyme inhibitory activity and function as potential molecules in the development of new drugs. In this study, the synthesized novel halogenated chalcones with bromobenzyl and methoxyphenyl moieties were evaluated toward the acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) enzymes and human erythrocyte carbonic anhydrase I (hCA I), and II (hCA II) isoenzymes. They showed highly potent inhibition ability toward AChE with Ki values of 1.83 ± 0.21–11.19 ± 0.96 nM and BChE with Ki values of 3.35 ± 0.91–26.70 ± 4.26 nM; hCA I with Ki values of 29.41 ± 3.14–57.63 ± 4.95 nM, and hCA II with Ki values of 24.00 ± 5.39–54.74 ± 1.65 nM. Among the tested enzyme inhibitions, compounds 14 and 13 were the most active compounds against AChE and BChE. Docking studies were performed to the most active compounds against AChE, BChE, hCA I and hCA II to propose a binding mode in the active site and molecular dynamics simulations were studied to check the molecular interactions and the stability of the ligands in the active site. The results may contribute to the development of new drugs particularly to treat some global disorders including Alzheimer's disease (AD), glaucoma, and diabetes.
RDL Kalıcı Kaydıİncele - ArticleYalnız künye2021Synthesis and biological evaluation of 3,5-diaryl-pyrazole derivatives as potential antiprostate cancer agents
Anil, Derya; Caykoylu, Emine U.; Sanli, Fatma; Gambacorta, Nicola; Karatas, Omer F.; Nicolotti, Orazio; Algul, Oztekin; Burmaoglu, Serdar
Prostate cancer is the most frequently diagnosed tumor in men and the second leading cause of cancer-associated mortality in most developed countries. 3,5-Diaryl substituted pyrazole derivatives (20–28) were prepared starting from related chalcones and biologically evaluated for in vitro growth inhibition activity against PC3 and DU145 human prostate cancer cell lines. Compounds 23, 26, and 28 were found to be more potent as compared to the other halogen-substituted derivatives. Especially, the 2-bromo-substituted pyrazole derivative (26) was found to be more potent against PC3 and DU145 cells. Epidermal growth factor receptor (EGFR) and vascular endothelial growth factor receptor 2 (VEGFR2) are known to be expressed in DU145 and PC3 cancer cells. The binding mode of the most selective compound 26 toward EGFR and VEGFR2 was investigated by employing docking simulations based on GLIDE standard precision (−5.912 and −6.949 kcal/mol, respectively).
RDL Kalıcı Kaydıİncele - ArticleAçık Erişim2021Synthesis of novel tris-chalcones and determination of their inhibition profiles against some metabolic enzymes
Burmaoglu, Serdar; Yilmaz, Ali Osman; Polat, M. Fatih; Kaya, Rüya; Gulcin, İlhami; Algul, Oztekin
In this study, we report the synthesis of novel tris-chalcones and testing of human carbonic anhydrase I, and II isoenzymes (hCA I, and hCA II), acetylcholinesterase (AChE), butyrylcholinesterase (BChE), and α-glycosidase (α-Gly) inhibitors for the development of novel chalcone structures towards for treatment of some diseases. The compounds demonstrated K i values between 13.6 ± 1.1 and 50.0 ± 17.1 nM on hCA I, 9.9 ± 0.8 and 39.5 ± 15.1 nM on hCA II, 3.1 ± 0.2 and 20.1 ± 1.9 nM on AChE, 4.9 ± 0.4 and 14.7 ± 5.2 nM on BChE and 3.9 ± 0.2 and 22.4 ± 10.7 nM on α-Gly enzymes. The results revealed that novel tris-chalcones can have promising drug potential for glaucoma, leukaemia, epilepsy; Alzheimer’s disease that was associated with the high enzymatic activity of hCA I, hCA II, AChE, and BChE enzymes.
RDL Kalıcı Kaydıİncele - ArticleAçık Erişim2021New chalcone derivatives as effective against SARS-CoV-2 agent
Duran, Nizami; Polat, M. Fatih; Aktas, Derya Anil; Alagoz, M. Abdullah; Ay, Emrah; Cimen, Funda; Tek, Erhan; Anil, Baris; Burmaoglu, Serdar; Algul, Oztekin
Aims: Flavonoids and related compounds, such as quercetin-based antiviral drug Gene-Eden-VIR/Novirin, inhibit the protease of severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2). The alkylated chalcones isolated from Angelica keiskei inhibit SARS-CoV proteases. In this study, we aimed to compare the anti-SARS CoV-2 activities of both newly synthesized chalcone derivatives and these two drugs. Methods: Determination of the potent antiviral activity of newly synthesized chalcone derivatives against SARS-CoV-2 by calculating the RT-PCR cycling threshold (Ct) values. Results: Antiviral activities of the compounds varied because of being dose dependent. Compound 6, 7, 9, and 16 were highly effective against SARS-CoV-2 at the concentration of 1.60 µg/mL. Structure-based virtual screening was carried out against the most important druggable SARS-CoV-2 targets, viral RNA-dependent RNA polymerase, to identify putative inhibitors that could facilitate the development of potential anti-coronavirus disease-2019 drug candidates. Conclusions: Computational analyses identified eight compounds inhibiting each target, with binding affinity scores ranging from −4.370 to −2.748 kcal/mol along with their toxicological, ADME, and drug-like properties.
RDL Kalıcı Kaydıİncele - ArticleAçık Erişim2019Synthesis and biological evaluation of novel tris-chalcones as potent carbonic anhydrase, acetylcholinesterase, butyrylcholinesterase and α-glycosidase inhibitors
Burmaoglu, Serdar; Yilmaz, Ali Osman; Polat, M. Fatih; Kaya, Rüya; Gulcin, İlhami; Algul, Oztekin
A novel class of fluoro-substituted tris-chalcones derivatives (5a-5i) was synthesized from phloroglucinol and corresponding benzaldehydes. A three step synthesis method was followed for the production of these tris-chalcone compounds. The structures of the newly synthesized compounds (5a-5i) were confirmed on the basis of IR, 1 H NMR, 13 C NMR, and elemental analysis. The compounds’ inhibitory activities were tested against human carbonic anhydrase I and II isoenzymes (hCA I and hCA II), acetylcholinesterase (AChE), butyrylcholinesterase (BChE), and α-glycosidase (α-Gly). These chalcone derivatives had K i values in the range of 19.58–78.73 nM for hCA I, 12.23–41.70 nM for hCA II, 1.09–6.84 nM for AChE, 8.30–32.30 nM for BChE and 0.93 ± 0.20–18.53 ± 5.06 nM against α-glycosidase. These results strongly support the promising nature of the tris-chalcone scaffold as selective carbonic anhydrase, acetylcholinesterase, butyrylcholinesterase, and α-glycosidase inhibitor. Overall, due to these derivatives’ inhibitory potential on the tested enzymes, they are promising drug candidates for the treatment of diseases like glaucoma, leukemia, epilepsy; Alzheimer's disease; type-2 diabetes mellitus that are associated with high enzymatic activity of carbonic anhydrase, acetylcholine esterase, butyrylcholinesterase, and α-glycosidase.
RDL Kalıcı Kaydıİncele - ArticleYalnız künye2019Synthesis, biological evaluation and molecular docking studies of bis-chalcone derivatives as xanthine oxidase inhibitors and anticancer agents
Burmaoglu, Serdar; Ozcan, S.; Balcioglu, S.; Gencel, M.; Noma, Samir Abbas Ali; Essiz, Sebnem; Ates, Burhan; Algul, Oztekin
In this study, a series of B-ring fluoro substituted bis-chalcone derivatives were synthesized by Claisen-Schmidt condensation reactions and evaluated for their ability to inhibit xanthine oxidase (XO) and growth inhibitory activity against MCF-7 and Caco-2 human cancer cell lines, in vitro. According to the results obtained, the bis-chalcone with fluoro group at the 2 (4b) or 2,5-position (4g) of B-ring were found to be potent inhibitors of the enzyme with IC50 values in the low micromolar range. The effects of these compounds were about 7 fold higher than allopurinol. The binding modes of the bis-chalcone derivatives in the active site of xanthine oxidase were explained using molecular docking calculations. Also, compound 4g and 4h showed in vitro growth inhibitory activity against a panel of two human cancer cell lines 1.9 and 6.8 μM of IC50 values, respectively.
RDL Kalıcı Kaydıİncele - ArticleYalnız künye2018Molecular docking studies on fluoro-substituted chalcones as potential DprE1 enzyme inhibitors
Yalcin, Gozde; Burmaoglu, Serdar; Yildiz, Ilkay; Algul, Oztekin
In this study, docking studies were performed on a series of fluoro-substituted chalcones (E1–E7, Z1-Z7, H1–H7) with DprE1 enzyme inhibition activities. The results showed that both the positions of the substituents and the type of chalcones seemed to be critical for their inhibition against DprE1. Chalcone derivatives exhibited binding affinity values of < −8.0 kcal/mol. The compounds E6, E7, and Z7 having a double bond in the linker group were effective inhibitors and it were found that this structural motif had an influence on the binding profile of molecules. The best docking results were detected for Z7, which is the cis-isomer of E7 from the E group. The SAR results of the novel DprE1 inhibitors were revealed in this study and the inhibitors were predicted to have excellent potencies from the developed models. The results could greatly contribute toward designing potential new DprE1 inhibitors with better activities.
RDL Kalıcı Kaydıİncele - ArticleYalnız künye2018Synthesis and biological evaluation of phloroglucinol derivatives possessing α-glycosidase, acetylcholinesterase, butyrylcholinesterase, carbonic anhydrase inhibitory activity
Burmaoglu, Serdar; Yilmaz, Ali O.; Taslimi, Parham; Algul, Oztekin; Kilic, Deryanur; Gulcin, Ilhami
A series of novel phloroglucinol derivatives were designed, synthesized, characterized spectroscopically and tested for their inhibitory activity against selected metabolic enzymes, including α-glycosidase, acetylcholinesterase (AChE), butyrylcholinesterase (BChE), and human carbonic anhydrase I and II (hCA I and II). These compounds displayed nanomolar inhibition levels and showed Ki values of 1.14–3.92 nM against AChE, 0.24–1.64 nM against BChE, 6.73–51.10 nM against α-glycosidase, 1.80–5.10 nM against hCA I, and 1.14–5.45 nM against hCA II.
RDL Kalıcı Kaydıİncele - ArticleAçık Erişim2017Design of potent fluoro-substituted chalcones as antimicrobial agents
Burmaoglu, Serdar; Algul, Oztekin; Gobek, Arzu; Aktas Anil, Derya; Ulger, Mahmut; Erturk, Busra Gul; Kaplan, Engin; Dogen, Aylin; Aslan, Gönül
Owing to ever-increasing bacterial and fungal drug resistance, we attempted to develop novel antitubercular and antimicrobial agents. For this purpose, we developed some new fluorine-substituted chalcone analogs (3, 4, 9–15, and 20–23) using a structure–activity relationship approach. Target compounds were evaluated for their antitubercular efficacy against Mycobacterium tuberculosis H37Rv and antimicrobial activity against five common pathogenic bacterial and three common fungal strains. Three derivatives (3, 9, and 10) displayed significant antitubercular activity with IC50 values of ≤16,760. Compounds derived from trimethoxy substituent scaffolds with monofluoro substitution on the B ring of the chalcone structure exhibited superior inhibition activity compared to corresponding hydroxy analogs. In terms of antimicrobial activity, most compounds (3, 9, 12–14, and 23) exhibited moderate to potent activity against the bacteria, and the antifungal activities of compounds 3, 13, 15, 20, and 22 were comparable to those of reference drugs ampicillin and fluconazole.
RDL Kalıcı Kaydıİncele - ArticleYalnız künye2016Synthesis and anti-proliferative activity of fluoro-substituted chalcones
Burmaoglu, Serdar; Algul, Oztekin; Anil, Derya Aktas; Gobek, Arzu; Duran, Gulay Gulbol; Ersan, Ronak Haj; Duran, Nizami
A series of novel fluoro-substituted chalcone derivatives have been synthesized. All synthesized compounds were characterized by 1H nuclear magnetic resonance (NMR), 13C NMR, and elemental analysis. Their anti-proliferative activities were evaluated against five cancer cells lines, namely, A549, A498, HeLa, A375, and HepG2 using the MTT method. Most of the compounds showed moderate to high activity with IC50 values in the range of 0.029-0.729 μM. Of all the synthesized compounds, 10 and 19 exhibited the most potent anti-proliferative activities against cancer cells, and 10 was identified as the most promising compound.
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