Browsing by Author "Ergan, Erdem"

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A Green Protocol for Simple One-Pot Synthesis of New Pyrimidine Derivatives Both Microwave Irradiation and Conventional Heating: Reactions, Characterization, and Theoretical Calculations
(Wiley, 2019) Akbas, Esvet; Ruzgar, Adem; Sahin, Ertan; Ergan, Erdem
In this research, 5-benzoyl-6-phenyl-4-(4-trifluoromethylphenyl)-2-{oxo and thioxo}-3,4-dihydro-1H-pyrimidines (1, 2) were synthesized by using multicomponent cyclocondensation reaction under microwave irradiation and classical heating. Compounds 3, 4, 6, 7, and 8 obtained reactions of 5-benzoyl-6-phenyl-4-(4-trifluoromethylphenyl)-2-thioxo-3,4-dihydro-1H-pyrimidine (1) and acetic anhydride, diethyl 2-bromomalonate, bromoacetic acid, 3-bromopropionic acid, methyl iodide, respectively. Compound 4 was both acetylated and hydrolyzed in acetic acid to give compound 5. The structures of all compounds were determined by using spectroscopic techniques like FT-IR, H-1/C-13 NMR, and elemental analyses, and the structures of compounds 1 and 3 were analyzed by X-ray crystal analysis. In addition, the quantum chemical parameters and full geometry optimizations for all compounds were computed using density functional theory based on B3LYP and the 6-31G (d, p) basis set.
Methylene Blue Adsorption From Aqueous Solution by Functionalized Perlites: an Experimental and Computational Chemistry Study
(desalination Publ, 2021) Sogut, Eda Gokirmak; Ergan, Erdem; Kilic, Necla Caliskan; Donmez, Hakan; Akbas, Esvet
In this study, 3-aminopropyltrimethoxy-silane (3-APTMS) and 3-mercaptopropyltrimethoxy-silane (3-MPTMS) were used to functionalize perlite in order to increase the adsorption capacity of methylene blue (MB). These materials were characterized by X-ray diffraction, X-ray fluorescence, Fourier transform infrared spectroscopy, scanning electron microscopy, and thermal (thermogravimetry/ differential thermal analysis) analyzes. The performance of perlite and functionalized derivatives was tested by adsorption of MB in a batch system under a variable pH (2-11) and initial MB concentration (10-60 mg L-1). Nonlinear and linear Langmuir, Freundlich, Dubinin-Radushkevich (D-R), and Sips adsorption equations were applied to define equilibrium isotherms. The maximum dye sorption was found to be at a pH of 11.0 (96.44% for P-A, 96.51% for P-APTMS, and 96.73% for P-MPTMS). The adsorption capacity for the dye was found to be 4.9445, 5.2014, and 5.3112 mg g(-1) for P-A, P-APTMS, and P-MPTMS, respectively, at 298 K. The adsorption kinetics was best described by the pseudo-second-order model. The obtained results confirm that amino and mercapto functional groups have positive effects on the adsorption of methylene blue by the adsorbents used in this work. Quantum chemical analysis supported better adsorption of methylene blue dye on amine and mercapto-functionalized perlite surfaces than the unmodified surface and the most suitable site for MB adsorption was suggested by Fukui function analysis.
Molecular Hybrid Design, Synthesis, in Vitro Cytotoxicity, in Silico Adme and Molecular Docking Studies of New Benzoate Ester-Linked Arylsulfonyl Hydrazones
(Mdpi, 2024) Ergan, Erdem; Cakmak, Resit; Basaran, Eyup; Mali, Suraj N.; Akkoc, Senem; Annadurai, Sivakumar
In this paper, we present the synthesis and characterization of two known sulfonyl hydrazides (1 and 2) and their new sulfonyl hydrazone derivatives (9-20), as well as in vitro and in silico investigations of their cytotoxic properties against human lung (A549) and human breast (MCF-7) cancer cell lines. The target compounds (9-20) obtained in high yields were synthesized for the first time by a multi-step reaction, and their structures were confirmed by elemental analysis and various spectral techniques, including FT-IR, 1H-, and 13C-NMR. The antiproliferative profiles of these compounds (1, 2, and 9-20) in this study were determined at concentrations of 200, 100, 50, and 25 mu M against selected cancer cell lines for 72 h using the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide (MTT) method. Except for compounds 1 and 2, other compounds (9-20) demonstrated cytotoxic activity at concentrations lower than 200 mu M. The newly synthesized compounds (9-20) demonstrated antiproliferative activities at a micromolar level, with IC50 values in the range of 29.59-176.70 mu M for the A549 cell line and 27.70-170.30 mu M for the MCF-7 cell line. Among these compounds, compound 15 (IC50 = 29.59 mu M against A549 cell line and IC50 = 27.70 mu M against MCF-7 cell line) showed the highest cytotoxic activity against these two cancer cell lines compared to the reference drug cisplatin (IC50 = 22.42 mu M against A549 cell line and IC50 = 18.01 mu M against MCF-7 cell line). From docking simulations, to establish a plausible binding mode of compounds, we noticed that compound 15 demonstrated the highest affinity (-6.8508 kcal/mol) for estrogen receptor-beta (ERbeta) compared to others, suggesting promising ERbeta binding potential. Most compounds followed Lipinski's rule of five, with acceptable logP values. Additionally, all had mixed gastrointestinal absorption and limited blood-brain barrier permeability. Overall, our study proposed new sulfonyl hydrazones as a potential class of anticancer agents.
Potansiyel Korozyon İnhibitörü Olarak Pirimidin Türevlerinin Dft Hesaplaması ile Teorikçalışmalar
(2021) Ergan, Erdem
Bu çalışmada pirimidin türevlerinin (1-12) korozyon önleme davranışları teorik kuantumkimyasal hesaplaması ile incelenmiştir. Tüm bileşikler için, moleküler elektrostatik potansiyel haritaları(MEP), En Yüksek İşgal Edilen Moleküler Orbital (HOMO), En Düşük Boş Moleküler Orbital(LUMO), elektronegatiflik (χ), kimyasal potansiyel (µ), global elektrofiliklik indeks (ω) ve kimyasalsertlik (η) gibi teorik hesaplamalarla elde edilen kuantum kimyasal parametreleri B3LYP / 6-31G (d, p)seviyesinde yoğunluk fonksiyonel teorisi (DFT) kullanılarak hesaplandı. Ayrıca, demir yüzeyi ilepirimidin türevi bileşikler arasında transfer edilen elektronların (ΔN) fraksiyonu hesaplandı. Bununlabirlikte, doğrusal olmayan optik (NLO) özellikler de incelenmiştir. Teorik hesaplamalarla elde edilenkuantum kimyasal parametreleri incelendiğinde, bileşik 10’un düşük Δ$E_{gap}$ ($E_{HOMO}$-$E_{LUMO}$), kimyasalsertlik (η) değerleri ve yüksek global elektrofilik indeksi, \"ΔN\" değerleri ile iyi bir korozyon önleyiciolarak kullanılabileceğini göstermiştir.
Synthesis of New Thiazine and Thiazole Derivatives Via Cyclization Reactions; Investigating Their Electronic Properties and Determination of Antioxidant Properties
(Wiley, 2022) Ergan, Erdem; Tozlu, Deniz
(4-[2,4-dimethoxyphenyl]-6-phenyl-2-thioxo-1,2,3,4-tetrahydropyrimidin-5-yl)(phenyl) methanone (1) have been prepared by Biginelli three-component cyclocondensation reaction of catalyzed with p-toluene sulfonic acid in ethanol. Pyrimido[2,1-b]thiazine (2) and thiazolo[3,2-a]pyrimidine (3) derivatives were obtained by a simple one-pot condensation reaction of starting compound 1 and 3-bromopropionic acid, bromoacetic acid and, respectively. By performing the reactions of compound 3 with heteroaromatic and aromatic aldehydes, arylidine-bicyclic thiazolo pyrimidine compounds (4-9) were synthesized. Theoretical calculations and molecular electrostatic potential maps of all synthesized compounds were performed using the Gaussian software package Density Functional Theory (DFT/6-31G: B3LYP). In addition, studies were carried out to determine the antioxidant properties of all the compounds obtained by the DPPH method, and compound 1 was found to be the most effective compound. The structures of the newly synthesized compounds were analyzed using spectroscopic methods such as IR, H-1, and C-13.
Synthesis of the 3,5-Diphenyl and Cytogenetic and Oxidative Alterations After Exposure of Cultured Human Whole Blood Cells
(Taylor & Francis As, 2017) Akbas, Esvet; Celikezen, Fatih Caglar; Turkez, Hasan; Ozdemir, Ozlem; Ruzgar, Adem; Ergan, Erdem; Sahin, Ertan
The 3,5-diphenyl-1H-pyrazole was obtained by condensation reaction of dibenzoylmethane and thiosemicarbazide in acetic acid under conventional heating and microwave irradiation method. The structure of the 3,5-diphenyl-1H-pyrazole confirmed by IR, H-1, and C-13 NMR and X-ray diffraction and the geometry optimization was carried out using density functional theory (DFT) methods at B3LYP/6-31G, 6-31G(d), 6-31G(d, p), 6-311G(d, p), 6-311G(2d, 2p), 6-31+G(d, p), 6-311++G(d, p) levels. In addition, cytotoxic and oxidative effects were investigated in cultured human peripheral blood cells.
Synthesis of Thiazole and Thiazine Derivative Compounds Obtained From New Thioxopyrimidine Compound, Investigation of Their Reactions With Substituted Aldehydes and Examining of Their Theoretically Electronic Properties
(2021) Tozlu, Deniz; Ergan, Erdem
Çalışmamızın ilk aşamasında multikomponent reaksiyonlardan biri olan Biginelli reaksiyonuyla, 1,3-difenil-1,3-propandion, 2,4-dimetoksibenzaldehit ve tiyoüre kullanılarak (4-(2,4-dimetoksifenil)-6-fenil-2-tiyokso-1,2,3,4-tetrahidropirimidin-5-il)(fenil)metanon (D-1) bileşiği sentezlendi. D-1 bileşiğinin bromopiruvik asit, 3-bromopropiyonik asit ve bromoasetik asit ile halkalanma tepkimeleri gerçekleştirilerek, pirimidin halkasına kondense tiyazin ve tiyazol (D-2, D-3 ve D-4) bileşikleri elde edildi. Son basamakta ise 6-benzoil-5-(2,4-dimetoksifenil)-7-fenil-5H-tiyazolo[3,2-a]pirimidin-3(2H)-on (D-4) bileşiğinin, sübstitüe benzaldehit türevleri ve 2-tiyofenkarboksaldehit bileşikleriyle tepkimeleri gerçekleştirildi. Sentezlenen tüm bileşiklerin teorik hesaplamaları ve moleküler elektrostatik potansiyel haritaları Gaussian paket programı kullanılarak Density Functional Theory (DFT/6-31G) teorisi ve B3LYP fonksiyonelleri ile incelendi. Elde edilen tüm pirimidin türevi bileşiklerin yapısal karakterizasyonları, elementel analiz, IR, 1H ve 13C NMR spektroskopik yöntemler kullanılarak aydınlatıldı.
Synthesis, Characterization, Quantum Chemical Studies and Electrochemical Performance of New 4,7-Dihydrotetrazolo[1,5 Derivatives
(indian Acad Sciences, 2019) Akbas, Esvet; Celik, Savas; Ergan, Erdem; Levent, Abdulkadir
In this study, 4,7-dihydrotetrazolo[1,5-a]pyrimidine derivatives (1-5) were prepared via Multicomponent Cyclocondensation Reactions (MCRs). All structures were determined by using FT-IR, 1H/13C NMR and elemental analyses. The compounds were investigated as corrosion inhibitors using density functional theory (DFT) at the level of B3LYP/6-31G (d, p). According to the calculations, compound 1 appears to be a good inhibitor for corrosion. In addition, the electrochemical properties of the novel systems were investigated by CV.Graphical Abstract:The synthesis, characterization, quantum chemical studies and electrochemical performance of new 4,7-dihydrotetrazolo[1,5-a]pyrimidine derivatives are reported.
Synthesis, Dft Calculations, Spectroscopy and in Vitro Antioxidant Activity Studies on 4-Hydroxyphenyl Substituted Thiopyrimidine Derivatives
(Elsevier, 2018) Akbas, Esvet; Ekin, Suat; Ergan, Erdem; Karakus, Yagmur
4-Hydroxyphenyl substituted thiopyrimidine derivatives have been synthesized with the starting compound 5-benzoyl-6-phenyl-4-(4-hydroxyphenyl)-1,2,3,4-tetrahydro-2-thioxopyrimidine (1). The compounds optimized geometrically with DFT in Gaussian at the B3LYP/6-31G (d, p) level in order to obtain information about the 3D geometries and electronic structures. The structures were characterized on the basis of H-1 NMR, C-13 NMR, FT-IR, and elemental analysis. All compounds tested in vitro in order to assess their antioxidant activity. On the biological properties including of free radical scavenging ability (DPPH center dot), ABTS(center dot+) assay, PhNHNH2 (phenyl hydrazine) induced haemolysis of erythrocytes and metal chelating activities were performed. The results were compared to standard antioxidants, such as alpha-tocopherol and trolox. The conclusion shows that the compounds thioxopyrimidine (1), dihydropyrimido [2,1-b][1,3]thiazin-4(6H)-one (4) and dihydropyrimidin-2(1H)-ylidene) malonate (5) exhibit a stronger antioxidant activity than the other derivatives. (C) 2018 Elsevier B.V. All rights reserved.
Synthesis, Dft Study and the Eschenmoser Sulfide Contraction of 1,2,3,4-Tetrahydropyrimidine Derivatives
(Chem Soc Pakistan, 2017) Akbas, Esvet; Erdogan, Ahmet; Ergan, Erdem; Gulcan, Mehmet; Ruzgar, Adem
5-Substituebenzoyl-4-aryl-6-substituephenyl-1,2,3,4-tetrahydro-2-(thioxo, oxo and imino) pyrimidines (4a-d) were synthesized via multicomponent cyclocondensation reaction. 7-Benzoyl- 8-phenyl-6-(4-carboxyphenyl)-2,3-dihydropyrimido[2,1-b][1,3] thiazin-4(6H)-one (5), 6-benzoyl- 2-methyl-7-phenyl-5-(4-carboxyphenyl)-3-oxo-2,3-dihydro-5H-thiazolo[ 3,2-a] pyrimidine (6) and 6-benzoyl-7-phenyl-5-(4-carboxyphenyl)-3-oxo-2,3-dihydro-5H-thiazolo[3,2-a] pyrimidine (7) were synthesized via reactions of starting compound 4e [1] and appropriate reagent compounds. When 4e was treated with alpha-bromoester in 1,4-dioxane (1/10 mL) it was resulted like the Eschenmoser sulfide contraction and compounds 8 was obtained. This method generally requires tertiary phosphine but instead of it we used pyridine as a catalyst. In addition, all synthesized pyrimidine derivatives have been optimized geometrically with DFT in Gaussian at the B3LYP/6-31G(d, p) level in order to obtain information about the 3D geometries and electronic structures.
Synthesis, Theoretical Calculation, Electrochemistry and Total Antioxidant Capacity of 5-Benzoy1 and Derivatives
(Elsevier, 2017) Ergan, Erdem; Akbas, Esvet; Levent, Abdulkadir; Sahin, Ertan; Konus, Metin; Seferoglu, Nurgul
5-Benzoy1-6-pheny1-4-(4-mehtoxyphenyI)-1,2,3,4-tetrahydro-2-thioxopyrimidine (1) have been prepared via Biginelli cyclocondensation reaction in acetic acid under reflux condition in good yield. The structure of 1 was determined by using spectroscopic techniques like H-1/C-13 NMR and elemental analyses. And also their molecular characterizations of compounds were analyzed by X-ray crystal analysis. A series of novel pyrimidine derivatives were obtained by reaction compound I with various reactive. All synthesized pyrimidine derivatives and related keto and enol tautomeric forms have been optimized geometrically with DFF in Gaussian at the B3LYP/6-31 + G (d, p) level in order to obtain information about the 3D geometries and electronic structures. The results showed that the keto tautomer is more stable than enol tautomer. However, the non-linear optical (NLO) properties were evaluated theoretically. The electrochemical properties of the novel compounds were investigated by CV and DPV. In addition, the total antioxidant capacities of all new synthesized compounds were measured in vitro by ABTS assay. (C) 2017 Elsevier B.V. All rights reserved.
Tetrahidro Pirimidin Türevlerinin Elektronik Özelliklerinin Belirlenmesi ve Korozyon Önleyici Olarak Kullanılabilirliğinin Araştırılması
(2021) Ergan, Erdem; Okay, Murat; Akbaş, Begüm Çağla; Akbas, Esvet
Metalik yapıların korozyonu, dünya çapındaki endüstrilerin çoğunda ciddi bir problemdir. Bu problem, metal yüzey üzerine, adsorpsiyon kabiliyetine sahip kimyasalların ilavesiyle kontrol edilebilir. İlgili kimyasallar sayesinde metal, bulunduğu korozif ortamdan izole edilebilir. Bu kimyasallar çoğunlukla işlevsel grup açısından zengin, serbest elektron çiftleri ve/veya π elektronları içeren gruplardan seçilir. Bu çalışmada yapısında eşleşmemiş elektron çiftleri, π elektronları, N, O ve S gibi fonksiyonel gruplar bulunduran pirimidin türevi bileşiklerin elektronik yapıları en yüksek dolu molekül orbitali (HOMO), en düşük boş molekül orbitali (LUMO), MEP, enerji gap (ΔE), iyonizasyon potansiyeli (I), elektron afinitesi (A), kimyasal sertlik ve yumuşaklığı (S), genel elektrofilik indeksi (ω), iletilen elektron fraksiyonindeksi (ΔN) ve geri kazanım (ΔEback-donation) özelliklerinin kuantum kimyasal hesaplama yöntemleri ile incelenmesi amaçlanmış ve bu doğrultuda seçilen bileşiklerin kuantum kimyasal hesaplama yöntemleri ile demir yüzeyine adsorbe olma yetenekleri ve korozyon önleyici etkileri çalışılmıştır. Bu çalışma ile sentezlenmiş bileşiklerin anti-korozyon malzeme olarak kullanım verimliliği tespit edilerek bu anlamda endüstriye yeni kazanımlar sağlanması hedeflenmiştir.
Theoretical Calculation of Newly Synthesized Tetrazolopyrimidine Derivatives as a Potential Corrosion Inhibitor
(Serbian Chemical Soc, 2022) Ergan, Erdem; Seker, Nurullah; Akbas, Begum Cagla; Akbas, Esvet
In this work, we wanted to define a general and comprehensive strategy for the synthesis of tetrazolo[1,5-a]pyrimidine derivatives. For this purpose, we obtained new tetrazolo[1,5-a]pyrimidine molecules via the mercury-promoted desulfurization reaction, including hydrolysis, cyclizations, and eliminations. All of the molecules were characterized by FT-IR, H-1-NMR, C-13-NMR, and elemental analysis. On the other hand, the potentials of compounds as corrosion inhibitors were calculated at B3LYP/6-31G (d, p) level via density functional theory (DFT).