Araştırma Makalesi
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Bazı Yeni Potansiyel Biyolojik Aktif 2-Etoksi-6-(3-substitue-4,5-dihidro-1H-1,2,4-triazol-5-on-4-il-azometin)-fenil Fenilasetat Türevlerinin Sentezi, Karakterizasyonu ve Antioksidan Özellikleri

Yıl 2023, Sayı: 46, 82 - 89, 31.01.2023
https://doi.org/10.31590/ejosat.1205579

Öz

1,2,4-Triazoller ve türevleri, tıbbi ve ilaç kimyası ve benzeri bir çok alanda ayrı bir yere sahiptir. Bunlar, çeşitli biyolojik aktivitelere sahip olan ve çok önemli roller oynayan çok sayıda heterosiklik bileşiğin sentezi için öncü bileşikler olarak da kullanılmaktadır. Bu çalışmada, trietilaminli ortamda yeni bir benzaldehid türevi olan 2-fenilasetoksi-3-etoksibenzaldehid bileşiğinin elde edilmesi için fenilasetil klorür ile 3-etoksi-2-hidroksibenzaldehitin reaksiyonu gerçekleştirilmiş olup sonrasında bu benzaldehid türevi ile literatürde mevcut olan dokuz tane amino bileşiğinin reaksiyonları sonucu heterohalkalı bileşiklerden 2-etoksi-6-(3-substitue-4,5-dihidro-1H-1,2,4-triazol-5-on-4-il-azometin)-fenil fenilasetat bileşiğinin sentezi gerçekleştirilmiştir. Çalışmanın devamında sentezlenen bazı 3 tipi bileşiklerin N-asetillendirme reaksiyonları da incelenmiş ve karşın olan 6 adet 2-etoksi-6-(1-asetil-3-substitue-4,5-dihidro-1H-1,2,4-triazol-5-on-4-il-azometin)-fenil fenilasetat bileşiklerinin sentezi gerçekleştirilmiştir. Bileşiklerin yapıları UV spektral verileri, 1H-NMR, 13C-NMR spektrumları ve IR verileri kullanılarak karakterize edildi. Bunun yanında 3c, 3f, 3i ve 4e bileşikleri için elementel analiz sonuçlarıda alınmıştır. Son olarak üç farklı yöntemle sentezlenen bileşiklerin in vitro potansiyel antioksidan aktiviteleri analiz edilmiştir.

Destekleyen Kurum

Kafkas Üniversitesi Bilimsel Araştırma Projeleri Koordinasyon Birimi

Proje Numarası

2011-FEF-31

Teşekkür

Ayrıca, yazarlar antioksidan aktivite incelemelerindeki katkısından dolayı Prof.Dr.Özlem Gürsoy-Kol’e teşekkür eder.

Kaynakça

  • Blois, S. (1955). A note on free radical formation in biologically occurring quinones. Biochimica et Biophysica Acta, 18, 165. https://doi.org/10.1016/0006-3002(55)90038-X
  • Demirbaş, N., Ugurluoglu, R., & Demirbaş, A. (2002). Synthesis of 3-alkyl(aryl)-4-alkylidenamino-4,5-dihydro-1H-1,2,4-triazol-5-ones and 3-alkyl-4-alkylamino-4,5-dihydro-1H-1,2,4-triazol-5-ones as antitumor agents. Bioorganic & Medicinal Chemistry, 10(12), 3717-3723. https://doi.org/10.1016/s0968-0896(02)00420-0
  • Dinis, T. C. P., Madeira, V. M. C., & Almeida, L. M. (1994). Action of Phenolic Derivatives (Acetaminophen, Salicylate, and 5-Aminosalicylate) as Inhibitors of Membrane Lipid Peroxidation and as Peroxyl Radical Scavengers. Archives of Biochemistry and Biophysics, 315(1), 161-169. https://doi.org/10.1006/abbi.1994.1485
  • Dobbs, K. D., Feldman, J., Marshall, W. J., McLain, S. J., McLaren, C. D., Meth, J. S., Vo, G. D., & Wang, Y. (2014). Phosphorescent Iridium(III) Complexes of Cyclometalated 5-Aryl-1H-1,2,4-Triazole Ligands: Structural, Computational, Spectroscopic, and Device Studies. The Journal of Physical Chemistry C, 118(48), 27763-27771. https://doi.org/10.1021/jp5096322
  • Hassan, F. A., & Younus, K. W. (2012). Biological Evaluation of Some Azole Derivatives in Cooling Fluids (Lubricant Oils). Research Journal of Biological Sciences, 7(1), 48-51. https://doi.org/10.3923/rjbsci.2012.48.51
  • Kavaklı, C., Akkaş Kavaklı, P., & Güven, O. (2014). Preparation and characterization of glycidyl methacrylate grafted 4-amino-1,2,4-triazole modified nonwoven fiber adsorbent for environmental application. Radiation Physics and Chemistry, 94, 111-114. https://doi.org/10.1016/j.radphyschem.2013.07.018
  • Khudair, Z., & Adnan, S. (2020). Synthesis and Characterization of Some New Heterocyclic Derivatives and Studying of their Biological Activity (Anti-Bacteria). International Journal of Pharmaceutical Qualıty Assurance, 11. https://doi.org/10.25258/ijpqa.11.1.6
  • Maddila, S., Pagadala, R., & Jonnalagadda, S. B. (2013). 1,2,4-Triazoles: A Review of Synthetic Approaches and the Biological Activity. Letters in Organic Chemistry, 10(10), 693-714.
  • Manap, S. (2022). Synthesis and in vitro antioxidant and antimicrobial activities of novel 3-alkyl(aryl)-4-[3-methoxy-4-(2-furylcarbonyloxy)-benzylidenamino]-4,5-dihydro-1H-1,2,4-triazol-5-ones, and their N-acetyl, N- Mannich base derivatives. Journal of the Iranian Chemical Society, 19(4), 1347-1368. https://doi.org/10.1007/s13738-021-02386-7
  • Manap, S., & Yüksek, H. (2021). Yeni Di-{2-[(3-alkil)-4,5-dihidro-1H-1,2,4-triazol-5-on-4-il)-azometin]-6-metoksi}-fenil Tereftalat Bileşiklerinin Sentezi ve Potansiyometrik Titrasyonları. Avrupa Bilim ve Teknoloji Dergisi, 31, Art. 31. https://doi.org/10.31590/ejosat.1006063
  • Murtaza, S., Akhtar, M. S., Kanwal, F., Abbas, A., Ashiq, S., & Shamim, S. (2017). Synthesis and biological evaluation of schiff bases of 4-aminophenazone as an anti-inflammatory, analgesic and antipyretic agent. Journal of Saudi Chemical Society, 21, S359-S372. https://doi.org/10.1016/j.jscs.2014.04.003
  • Oyaizu, M. (1986). Studies on products of browning reaction. Antioxidative activities of products of browning reaction prepared from glucosamine. The Japanese Journal of Nutrition and Dietetics, 44(6), 307-315. https://doi.org/10.5264/eiyogakuzashi.44.307
  • Shneine, J., & Alaraji, Y. (2016). Chemistry of 1, 2, 4-Triazole: A Review Article. International Journal of Science and Research (IJSR), 5, 1411.

Synthesis Characterization and Antioxidant Properties of Some New Potential Biologically Active 2-Ethoxy-6-(3-substitue-4,5-dihydro-1H-1,2,4-triazol-5-one-4-yl-azomethine)-phenyl Phenylacetate Derivatives

Yıl 2023, Sayı: 46, 82 - 89, 31.01.2023
https://doi.org/10.31590/ejosat.1205579

Öz

1,2,4-Triazoles and their derivatives have a special place in many fields such as medicinal and pharmaceutical chemistry and so on. They are also used as vanguards for the synthesis of numerous heterocyclic compounds that have various biological activities and play very important roles. In this study, the reaction of phenylacetyl chloride and 3-ethoxy-2-hydroxybenzaldehyde was carried out to obtain 2-phenylacetoxy-3-ethoxybenzaldehyde, a new benzaldehyde derivative, in the presence of triethylamine. Synthesis of 2-ethoxy-6-(3-substitue-4,5-dihydro-1H-1,2,4-triazol-5-one-4-yl-azomethine)-phenyl phenylacetate compouns were carried out.In the continuation of the study, the N-acetylation reactions of some 3-type matters synthesized were also examined and the synthesis of six 2-ethoxy-6-(1-acetyl-3-substitue-4,5-dihydro-1H-1,2,4-triazol-5-one-4-yl-azomethine)-phenyl phenylacetate compounds was performed.The structures of the compounds were characterized using UV spectral data, 1H-NMR, 13C-NMR and IR data. In addition, elemental analysis results were obtained for 3c, 3f, 3i and 4e compounds. Finally, in vitro potential antioxidant activities of compounds synthesized by three different methods were analyzed.

Proje Numarası

2011-FEF-31

Kaynakça

  • Blois, S. (1955). A note on free radical formation in biologically occurring quinones. Biochimica et Biophysica Acta, 18, 165. https://doi.org/10.1016/0006-3002(55)90038-X
  • Demirbaş, N., Ugurluoglu, R., & Demirbaş, A. (2002). Synthesis of 3-alkyl(aryl)-4-alkylidenamino-4,5-dihydro-1H-1,2,4-triazol-5-ones and 3-alkyl-4-alkylamino-4,5-dihydro-1H-1,2,4-triazol-5-ones as antitumor agents. Bioorganic & Medicinal Chemistry, 10(12), 3717-3723. https://doi.org/10.1016/s0968-0896(02)00420-0
  • Dinis, T. C. P., Madeira, V. M. C., & Almeida, L. M. (1994). Action of Phenolic Derivatives (Acetaminophen, Salicylate, and 5-Aminosalicylate) as Inhibitors of Membrane Lipid Peroxidation and as Peroxyl Radical Scavengers. Archives of Biochemistry and Biophysics, 315(1), 161-169. https://doi.org/10.1006/abbi.1994.1485
  • Dobbs, K. D., Feldman, J., Marshall, W. J., McLain, S. J., McLaren, C. D., Meth, J. S., Vo, G. D., & Wang, Y. (2014). Phosphorescent Iridium(III) Complexes of Cyclometalated 5-Aryl-1H-1,2,4-Triazole Ligands: Structural, Computational, Spectroscopic, and Device Studies. The Journal of Physical Chemistry C, 118(48), 27763-27771. https://doi.org/10.1021/jp5096322
  • Hassan, F. A., & Younus, K. W. (2012). Biological Evaluation of Some Azole Derivatives in Cooling Fluids (Lubricant Oils). Research Journal of Biological Sciences, 7(1), 48-51. https://doi.org/10.3923/rjbsci.2012.48.51
  • Kavaklı, C., Akkaş Kavaklı, P., & Güven, O. (2014). Preparation and characterization of glycidyl methacrylate grafted 4-amino-1,2,4-triazole modified nonwoven fiber adsorbent for environmental application. Radiation Physics and Chemistry, 94, 111-114. https://doi.org/10.1016/j.radphyschem.2013.07.018
  • Khudair, Z., & Adnan, S. (2020). Synthesis and Characterization of Some New Heterocyclic Derivatives and Studying of their Biological Activity (Anti-Bacteria). International Journal of Pharmaceutical Qualıty Assurance, 11. https://doi.org/10.25258/ijpqa.11.1.6
  • Maddila, S., Pagadala, R., & Jonnalagadda, S. B. (2013). 1,2,4-Triazoles: A Review of Synthetic Approaches and the Biological Activity. Letters in Organic Chemistry, 10(10), 693-714.
  • Manap, S. (2022). Synthesis and in vitro antioxidant and antimicrobial activities of novel 3-alkyl(aryl)-4-[3-methoxy-4-(2-furylcarbonyloxy)-benzylidenamino]-4,5-dihydro-1H-1,2,4-triazol-5-ones, and their N-acetyl, N- Mannich base derivatives. Journal of the Iranian Chemical Society, 19(4), 1347-1368. https://doi.org/10.1007/s13738-021-02386-7
  • Manap, S., & Yüksek, H. (2021). Yeni Di-{2-[(3-alkil)-4,5-dihidro-1H-1,2,4-triazol-5-on-4-il)-azometin]-6-metoksi}-fenil Tereftalat Bileşiklerinin Sentezi ve Potansiyometrik Titrasyonları. Avrupa Bilim ve Teknoloji Dergisi, 31, Art. 31. https://doi.org/10.31590/ejosat.1006063
  • Murtaza, S., Akhtar, M. S., Kanwal, F., Abbas, A., Ashiq, S., & Shamim, S. (2017). Synthesis and biological evaluation of schiff bases of 4-aminophenazone as an anti-inflammatory, analgesic and antipyretic agent. Journal of Saudi Chemical Society, 21, S359-S372. https://doi.org/10.1016/j.jscs.2014.04.003
  • Oyaizu, M. (1986). Studies on products of browning reaction. Antioxidative activities of products of browning reaction prepared from glucosamine. The Japanese Journal of Nutrition and Dietetics, 44(6), 307-315. https://doi.org/10.5264/eiyogakuzashi.44.307
  • Shneine, J., & Alaraji, Y. (2016). Chemistry of 1, 2, 4-Triazole: A Review Article. International Journal of Science and Research (IJSR), 5, 1411.
Toplam 13 adet kaynakça vardır.

Ayrıntılar

Birincil Dil Türkçe
Konular Mühendislik
Bölüm Makaleler
Yazarlar

Haydar Yüksek 0000-0003-1289-1800

Faruk Kardaş 0000-0002-0900-7503

Sevda Manap 0000-0002-5025-9622

Proje Numarası 2011-FEF-31
Erken Görünüm Tarihi 31 Ocak 2023
Yayımlanma Tarihi 31 Ocak 2023
Yayımlandığı Sayı Yıl 2023 Sayı: 46

Kaynak Göster

APA Yüksek, H., Kardaş, F., & Manap, S. (2023). Bazı Yeni Potansiyel Biyolojik Aktif 2-Etoksi-6-(3-substitue-4,5-dihidro-1H-1,2,4-triazol-5-on-4-il-azometin)-fenil Fenilasetat Türevlerinin Sentezi, Karakterizasyonu ve Antioksidan Özellikleri. Avrupa Bilim Ve Teknoloji Dergisi(46), 82-89. https://doi.org/10.31590/ejosat.1205579