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Synthesis, Biological and Acidic Properties of Novel 2-Methoxy-6-[(3-Alkyl/Aryl-4,5-Dihydro-1H- 1,2,4-Triazol-5-one-4-yl)-Azomethin]-Phenyl p-Nitrobenzoate Derivatives

Haydar Yüksek1, Hilal Medetalibeyoğlu1, Mehmet Karadağ1, Sevda Manap1
Affiliation: 
1 Department of Chemistry, Kafkas University, Kars, 36100, Turkey hhigh61@gmail.com
DOI: 
https://doi.org/10.23939/chcht17.04.766
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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.
References: 

[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
https://doi.org/10.1002/cbdv.202100433

[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
https://doi.org/10.23939/chcht14.02.214

[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
https://doi.org/10.56042/ijc.v61i6.64214

[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
https://doi.org/10.1002/ardp.201300048

[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
https://doi.org/10.23939/chcht12.02.167

[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
https://doi.org/10.2174/1573406411309030002

[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
https://doi.org/10.1016/j.ejmech.2009.05.022

[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.
https://doi.org/10.2174/15701786113109990001

[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
https://doi.org/10.52568/000672/JCSP/42.04.2020

[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
https://doi.org/10.1016/j.heliyon.2019.e01809

[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
https://doi.org/10.1007/s00044-015-1334-8

[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.

[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
https://doi.org/10.1155/2010/407603

[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
https://doi.org/10.3390/90400232

[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
https://doi.org/10.3390/12081805

[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.

[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
https://doi.org/10.1021/je00017a046

[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
https://doi.org/10.1021/ja00755a024

[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
https://doi.org/10.1080/00304949309457935

[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
https://doi.org/10.1016/S0378-8741(98)00055-5

[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
https://doi.org/10.1016/j.ejmech.2004.06.007