Synthesis, Biological and Acidic Properties of Novel 2-Methoxy-6-[(3-Alkyl/Aryl-4,5-Dihydro-1H1,2,4-Triazol-5-one-4-yl)-Azomethin]-Phenyl p-Nitrobenzoate Derivatives
| dc.citation.epage | 773 | |
| dc.citation.issue | 4 | |
| dc.citation.spage | 766 | |
| dc.contributor.affiliation | Kafkas University | |
| dc.contributor.author | Yüksek, Haydar | |
| dc.contributor.author | Medetalibeyoğlu, Hilal | |
| dc.contributor.author | Karadağ, Mehmet | |
| dc.contributor.author | Manap, Sevda | |
| dc.coverage.placename | Львів | |
| dc.coverage.placename | Lviv | |
| dc.date.accessioned | 2025-03-05T08:54:18Z | |
| dc.date.created | 2023-02-28 | |
| dc.date.issued | 2023-02-28 | |
| dc.description.abstract | 3-Алкіл/арил-4-аміно-4,5-дигідро-1Н-1,2,4-триазол-5-они (2) реагують з 2-(p-нітробензокси)-3-метоксибензальдегідом (3) з утворенням відповідних 2-метокси-6-[(3-алкіл/арил-4,5-дигідро-1Н-1,2,4-триазол-5-он-4-іл)азометин]феніл-п-нітробензоатів (4). Досліджено реакції ацетилювання сполук 4 й отримано N-ацетильні похідні типу 5. Нові синтезовані сполуки було повністю охарактеризовано. Крім того, антибактеріальну активність чотирнадцяти нових сполук in vitro було перевірено проти шести бактерій за допомогою методу дифузії в агаровому середовищі. Також нові синтезовані сполуки типу 4 потенціометрично титрували тетрабутиламоній гідроксидом (TBAH) у п'яти неводних розчинниках. | |
| dc.description.abstract | 3-Alkyl/Aryl-4-amino-4,5-dihydro-1H-1,2,4-triazol-5-ones (2) reacted with 2-(p-nitrobenzoxy)-3-methoxybenzaldehyde (3) to afford the corresponding 2-methoxy-6-[(3-alkyl/aryl-4,5-dihydro-1H-1,2,4-triazol-5-one-4-yl)-azomethin]-phenyl p-nitrobenzoates (4). The acetylation reactions of compounds 4 were investigated, and 5 type N-acetyl derivatives were obtained. The newly synthesized compounds were fully characterized. Also, in vitro antibacterial activities of the fourteen new compounds were screened against six bacteria according to agar well diffusion method. Finally, the newly synthesized 4 type compounds were titrated potentiometrically with tetrabutylammonium hydroxide (TBAH) in five non-aqueous solvents. | |
| dc.format.extent | 766-773 | |
| dc.format.pages | 8 | |
| dc.identifier.citation | Synthesis, Biological and Acidic Properties of Novel 2-Methoxy-6-[(3-Alkyl/Aryl-4,5-Dihydro-1H1,2,4-Triazol-5-one-4-yl)-Azomethin]-Phenyl p-Nitrobenzoate Derivatives / Haydar Yüksek, Hilal Medetalibeyoğlu, Mehmet Karadağ, Sevda Manap // Chemistry & Chemical Technology. — Lviv : Lviv Politechnic Publishing House, 2023. — Vol 17. — No 4. — P. 766–773. | |
| dc.identifier.citationen | Synthesis, Biological and Acidic Properties of Novel 2-Methoxy-6-[(3-Alkyl/Aryl-4,5-Dihydro-1H1,2,4-Triazol-5-one-4-yl)-Azomethin]-Phenyl p-Nitrobenzoate Derivatives / Haydar Yüksek, Hilal Medetalibeyoğlu, Mehmet Karadağ, Sevda Manap // Chemistry & Chemical Technology. — Lviv : Lviv Politechnic Publishing House, 2023. — Vol 17. — No 4. — P. 766–773. | |
| dc.identifier.doi | doi.org/10.23939/chcht17.04.766 | |
| dc.identifier.uri | https://ena.lpnu.ua/handle/ntb/63711 | |
| dc.language.iso | en | |
| dc.publisher | Видавництво Львівської політехніки | |
| dc.publisher | Lviv Politechnic Publishing House | |
| dc.relation.ispartof | Chemistry & Chemical Technology, 4 (17), 2023 | |
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| dc.relation.references | [19] Ikizler, A.; Yüksek, H. Acetylation of 4-Amino-4,5-dihydro-1H-1,2,4-triazol-5-ones. Org Prep Proced Int. 1993, 25, 99–105. https://doi.org/10.1080/00304949309457935 | |
| dc.relation.references | [20] Ahmad, I.; Mehmood, Z.; Mohammad, F. Screening of Some Indian Medicinal Plants for Their Antimicrobial Properties. J Ethnopharmacol 1998, 62, 183–193. https://doi.org/10.1016/S0378-8741(98)00055-5 | |
| dc.relation.references | [21] Demirbaş, N.; Karaoğlu, Ş.A.; Demirbaş, A.; Sancak, K. Synthesis and Antimicrobial Activities of Some New 1-(5-Phenylamino-[1,3,4]thiadiazol-2-yl)methyl-5-oxo-[1,2,4]triazole and 1-(4-Phenyl-5-thioxo-[1,2,4]triazol-3-yl)methyl-5-oxo-[1,2,4]triazole Derivatives. Eur. J. Med. Chem. 2004, 39, 793–804. https://doi.org/10.1016/j.ejmech.2004.06.007 | |
| dc.relation.referencesen | [1] Boy, S.; Aras, A.; Türkan, F.; Akyıldırım, O.; Beytur, M.; Sedef Karaman, H.; Manap, S.; Yüksek, H. Synthesis, Spectroscopic Analysis, and in vitro/in silico Biological Studies of Novel Piperidine Derivatives Heterocyclic Schiff-Mannich Base Compounds. Chem. Biodivers. 2021, 18, e2100433. https://doi.org/10.1002/cbdv.202100433 | |
| dc.relation.referencesen | [2] Perekhoda, L.; Georgiyants, V.; Yeromina, H.; Drapak, I.; Lubenets, V.; Ieromina, Z.; Sych, I.; Severina, H.; Demchenko, A. The Synthesis and in silico Antihypertensive Activity Prognosis of New Mannich Bases Containing the 1,2,4-Triazole Moiety. Chem. Chem. Technol. 2020, 14, 214–220. https://doi.org/10.23939/chcht14.02.214 | |
| dc.relation.referencesen | [3] Yüksek, H.; Berkyürek, A.; Manap, S.; Özdemir, G.; Beytur, M.; Balseven, H.; Alkan, M., Aytemiz, F.; Gürsoy-Kol, Ö. Synthesis, Characterization and Investigation of Antimicrobial and Antioxidant Activities of Some New 2-[(4,5-Dihydro-1H-1,2,4-triazol-5-one-4-yl)azomethine]phenyl 4-nitrobenzoate Derivatives. Indian J. Chem. 2022, 61, 623–634. https://doi.org/10.56042/ijc.v61i6.64214 | |
| dc.relation.referencesen | [4] Yüksek, H.; Akyıldırım, O.; Yola, M.L.; Gürsoy-Kol, Ö.; Çelebier, M.; Kart, D. Synthesis, in vitro Antimicrobial and Antioxidant Activities of Some New 4,5-Dihydro-1H-1,2,4-triazol-5-one Derivatives. Archiv Der Pharm. 2013, 346, 470–480. https://doi.org/10.1002/ardp.201300048 | |
| dc.relation.referencesen | [5] Shakh, Y.; Slesarchuk, M.; Syngaevsky, V.; Bolibrukh, B.; Karkhut, A.; Polovkovych, S.; Shevchuk, L.; Novikov, V. Interaction of 5-Substituted 1,4-Naphthoquinones and Amino Thiotriazoles: Reaction Ways and Regioselectivity. Chem. Chem. Technol. 2018, 12, 167–175. https://doi.org/10.23939/chcht12.02.167 | |
| dc.relation.referencesen | [6] Kaczor, A.A.; Pitucha, M.; Karczmarzyk, Z.; Wysocki, W.; Rzymowska, J.; Matosiuk, D. Structural and Molecular Docking Studies of 4-Benzyl-3-[(1-methylpyrrol-2-yl)methyl]-4, 5-dihydro-1H-1, 2, 4-triazol-5-one with Anticancer Activity. Med Chem 2013, 9, 313–328. https://doi.org/10.2174/1573406411309030002 | |
| dc.relation.referencesen | [7] Bayrak, H.; Demirbas, A.; Demirbas, N.; Albay Karaoğlu, S. Synthesis of Some New 1,2,4-Triazoles Starting from İsonicotinic Acid Hydrazide and Evaluation of their Antimicrobial Activities. Eur. J. Med. Chem. 2009, 44, 4362–4366. https://doi.org/10.1016/j.ejmech.2009.05.022 | |
| dc.relation.referencesen | [8] Gökçe, H.; Bahçeli, S.; Akyıldırım, O.; Yüksek, H.; Gürsoy-Kol, Ö. The Syntheses, Molecular Structures, Spectroscopic Properties (IR, Micro–Raman, NMR and UV–vis) and DFT Calculations of Antioxidant 3–Alkyl–4–[3–methoxy–4–(4–methylbenzoxy)-benzylidenamino]–4,5–dihydro–1H–1,2,4–triazol–5–one Molecules. Lett. Org. Chem. 2013, 10, 395–441. | |
| dc.relation.referencesen | [9] Yüksek, H.; Özdemir, G.; Gürsoy Kol, Ö.; Manap, S. Synthesis, in vitro Antioxidant and Antimicrobial Activities of Some New 2-(3-Alkyl/Aryl-4,5-dihydro-1H-1,2,4-triazol-5-on-4-yl-azomethine)-phenyl Benzenesulfonate Derivatives. J. Chem. Soc. Pak. 2020, 42, 624–633. https://doi.org/10.52568/000672/JCSP/42.04.2020 | |
| dc.relation.referencesen | [10] Beytur, M.; Turhan-Irak, Z.; Yüksek, H. Synthesis, Characterization and Theoretical Determination of Corrosion İnhibitor Activities of Some New 4,5-Dihydro-1H-1,2,4-Triazol-5-one Derivatives. Heliyon 2019, 5, e01809. https://doi.org/10.1016/j.heliyon.2019.e01809 | |
| dc.relation.referencesen | [11] Aktaş-Yokuş, Ö.; Yüksek, H.; Gürsoy-Kol, Ö.; Alpay-Karaoğlu, S. Synthesis and Biological Evaluation of New 1,2,4-Triazole Derivatives with their Potentiometric Titrations. Med Chem Res. 2015, 24, 2813–2824. https://doi.org/10.1007/s00044-015-1334-8 | |
| dc.relation.referencesen | [12] Bahçeci, Ş.; Yüksek, H.; Ocak, Z.; Köksal, C.; Özdemir, M. Synthesis and Non-aqueous Medium Titrations of Some New 4,5-Dihydro-1H-1,2,4-triazol-5-one Derivatives. Acta Chim. Slov. 2002, 49, 783–794. | |
| dc.relation.referencesen | [13] Gürsoy Kol, Ö.; Yüksek, H. Synthesis and ın-vitro Antioxidant Evaluation of Some Novel 4,5-Dihydro-1H-1,2,4-triazol-5-one Derivatives. J Chem 2010, 7, 407603. https://doi.org/10.1155/2010/407603 | |
| dc.relation.referencesen | [14] Yüksek, H.; Ocak, Z.; Alkan, M.; Bahçeci, Ş.; Ocak, M.; Özdemir, M. Synthesis and Determination of pKa Values of Some New 3,4-Disubstituted-4,5-dihydro-1H-1,2,4-triazol-5-one Derivatives in Non-aqueous solvents. Molecules 2004, 9, 232–240. https://doi.org/10.3390/90400232 | |
| dc.relation.referencesen | [15] Alkan, M.; Yüksek, H.; İslamoğlu, F.; Bahçeci, Ş.; Calapoğlu, M.; Elmastaş, M.; Akşit, H.; Özdemir, M. A Study on 4-Acylamino-4,5-dihydro-1H-1,2,4-triazol-5-ones, Molecules 2007, 12, 1805–1816. https://doi.org/10.3390/12081805 | |
| dc.relation.referencesen | [16] Gürbüz, A.; Alkan, M.; Manap, S.; Özdemir, G.; Yüksek, H. Synthesis and Antimicrobial Activities of Novel 2-Methoxy-6-[(3-alkyl-4,5-dihydro-1H-1,2,4-triazol-5-one-4-yl)-azomethin]-phenyl Benzoates with Their Nonaqueous Medium Titrations. World J. Pharm. Pharm. Sci. 2021, 10, 65–68. | |
| dc.relation.referencesen | [17] Putun, A.E.; Bereket, G.; Keskin, E. Potentiometric Titrations of Some 2-Substituted 5-nitrobenzimidazole Derivatives in Nonaqueous Solvent. J. Chem. Eng. Data 1995, 40, 221–224. https://doi.org/10.1021/je00017a046 | |
| dc.relation.referencesen | [18] Frey, P.A.; Kokesh, F.C.; Westheimer, F.H. A Reporter Group at Active Site of Acetoacetate Decarboxylase. I. Ionization Constant of the Nitrophenol. J. Am. Chem. Soc. 1971, 93, 7266-7269. https://doi.org/10.1021/ja00755a024 | |
| dc.relation.referencesen | [19] Ikizler, A.; Yüksek, H. Acetylation of 4-Amino-4,5-dihydro-1H-1,2,4-triazol-5-ones. Org Prep Proced Int. 1993, 25, 99–105. https://doi.org/10.1080/00304949309457935 | |
| dc.relation.referencesen | [20] Ahmad, I.; Mehmood, Z.; Mohammad, F. Screening of Some Indian Medicinal Plants for Their Antimicrobial Properties. J Ethnopharmacol 1998, 62, 183–193. https://doi.org/10.1016/S0378-8741(98)00055-5 | |
| dc.relation.referencesen | [21] Demirbaş, N.; Karaoğlu, Ş.A.; Demirbaş, A.; Sancak, K. Synthesis and Antimicrobial Activities of Some New 1-(5-Phenylamino-[1,3,4]thiadiazol-2-yl)methyl-5-oxo-[1,2,4]triazole and 1-(4-Phenyl-5-thioxo-[1,2,4]triazol-3-yl)methyl-5-oxo-[1,2,4]triazole Derivatives. Eur. J. Med. Chem. 2004, 39, 793–804. https://doi.org/10.1016/j.ejmech.2004.06.007 | |
| dc.relation.uri | https://doi.org/10.1002/cbdv.202100433 | |
| dc.relation.uri | https://doi.org/10.23939/chcht14.02.214 | |
| dc.relation.uri | https://doi.org/10.56042/ijc.v61i6.64214 | |
| dc.relation.uri | https://doi.org/10.1002/ardp.201300048 | |
| dc.relation.uri | https://doi.org/10.23939/chcht12.02.167 | |
| dc.relation.uri | https://doi.org/10.2174/1573406411309030002 | |
| dc.relation.uri | https://doi.org/10.1016/j.ejmech.2009.05.022 | |
| dc.relation.uri | https://doi.org/10.52568/000672/JCSP/42.04.2020 | |
| dc.relation.uri | https://doi.org/10.1016/j.heliyon.2019.e01809 | |
| dc.relation.uri | https://doi.org/10.1007/s00044-015-1334-8 | |
| dc.relation.uri | https://doi.org/10.1155/2010/407603 | |
| dc.relation.uri | https://doi.org/10.3390/90400232 | |
| dc.relation.uri | https://doi.org/10.3390/12081805 | |
| dc.relation.uri | https://doi.org/10.1021/je00017a046 | |
| dc.relation.uri | https://doi.org/10.1021/ja00755a024 | |
| dc.relation.uri | https://doi.org/10.1080/00304949309457935 | |
| dc.relation.uri | https://doi.org/10.1016/S0378-8741(98)00055-5 | |
| dc.relation.uri | https://doi.org/10.1016/j.ejmech.2004.06.007 | |
| dc.rights.holder | © Національний університет “Львівська політехніка”, 2023 | |
| dc.rights.holder | © Yüksek H., Medetalibeyoğlu H., Karadağ M., Manap S., 2023 | |
| dc.subject | 1 | |
| dc.subject | 2 | |
| dc.subject | 4-триазол-5-он | |
| dc.subject | основа Шиффа | |
| dc.subject | ацетилювання | |
| dc.subject | антимікробна активність | |
| dc.subject | pKa | |
| dc.subject | 1 | |
| dc.subject | 2 | |
| dc.subject | 4-triazol-5-one | |
| dc.subject | Schiff base | |
| dc.subject | acetylation | |
| dc.subject | antimicrobial activity | |
| dc.subject | pKa | |
| dc.title | Synthesis, Biological and Acidic Properties of Novel 2-Methoxy-6-[(3-Alkyl/Aryl-4,5-Dihydro-1H1,2,4-Triazol-5-one-4-yl)-Azomethin]-Phenyl p-Nitrobenzoate Derivatives | |
| dc.title.alternative | Синтез, біологічні та кислотні властивості нових нових похідних 2-метокси-6-[(3-алкіл/арил-4,5-дигідро-1H-1,2,4-триазол-5-он-4-іл)азометин]феніл-p-нітробензоату | |
| dc.type | Article |
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