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Yeni 1H-1,2,3-triazol türevleri: Sentez, Karakterizasyon ve Antioksidan Aktivite

Yıl 2025, Cilt: 7 Sayı: 2, 191 - 194, 31.05.2025
https://doi.org/10.51435/turkjac.1681862

Öz

4-bromo-N-(4-((1-(4-bromobenzil)-1H-1,2,3-triazol-4-il)metoksi)-3-metoksi benziliden) anilin (3), 2-((1-(3-(1,3-dioksoizoindolin-2-il) propil)-1H-1,2,3-triazol-4-il)metoksi) benzaldehit (6) ve 4-((1-(3-(1,3-dioksoizoindolin-2-il)propil) -1H-1,2,3-triazol-4-il)metoksi)-3-metoksibenzaldehit (8) sentezlendi. Bileşikler FTIR, 1H-NMR ve 13C-NMR spektroskopik yöntemleri ile karakterize edildi. Bileşiklerin antioksidan özellikleri yaygın olarak kabul görmüş iki metodoloji deneyi (DPPH ve FRAP) kullanılarak değerlendirildi. Bileşik 3, bileşikler arasında en yüksek antioksidan potansiyeline sahip olanıdır.

Kaynakça

  • F. Çelik, Y. Ünver, B. Barut, A. Özel, K. Sancak, Synthesis, Characterization and Biological Activities of New Symmetric Bis-1,2,3-Triazoles with Click Chemistry, Medicinal Chemistry, 2018, 230-241.
  • E. Düğdü, D. Ünlüer, F. Çelik, K. Sancak, Ş. A. Karaoğlu, A. Özel, Synthesis of Novel Symmetrical 1,4-Disubstituted 1,2,3-Bistriazole Derivatives via ‘Click Chemistry’ and Their Biological Evaluation, Molecules, 21, 2019, 659-672.
  • F. Çelik, F. Türkan, A. Aras, M. N. Atalar, H. S. Karaman, Y. Ünver, N. Kahriman, Synthesis of novel 1,2,3 Triazole Derivatives and Assessment of Their Potential Cholinesterases, Glutathione S-transferase Enzymes Inhibitory Properties: An in Vitro and in Silico Study, Bioorganic Chemistry, 107, 2021.
  • R. P. Frutos, S. Rodriguez, N. D. Patel, D. Reeves, T. Tampone, C.H. Senanayake, A General and Practical Synthesis of N-Aryl-3- 4-(imidazol-4-yl)-1,2,3-triazol-1-yl benzamide Anti-Inflammatory Cytokine Inhibitors, Asian Journal of Organic Chemistry, 3, 2014, 769-772.
  • R. Jain, P. Gahlyan, S. Dwivedi, R. Konwar, S. Kumar, M. Bhandari, R. Arora, R. Kakkar, R. Kumar, A.K. Prasad, Design, Synthesis and Evaluation of 1H-1,2,3-Triazol-4-yl-methyl Tethered 3-Pyrrolylisatins as Potent Anti-Breast Cancer Agents, Chemistry Select, 19, 2018, 5263-5268.
  • D. L. Jardim, M. Schwaederle, D. S. Hong, R. Kurzrock, An appraisal of drug development timelines in the Era of precision oncology, Oncotarget, 7, 2016, 53037-53046.
  • V. Judge, B. Narasimhan, M. Ahuja, D. Sriram, P. Yogeeswari, Isonicotinic Acid Hydrazide Derivatives: Synthesis, Antimycobacterial, Antiviral, Antimicrobial Activity and QSAR Studies, Letters in Drug Design & Discovery, 8, 2011, 792-810.
  • V. Judge, B. Narasimhan, M. Ahuja, D. Sriram, P. Yogeeswari, E. De Clercq, C. Pannecouque, J. Balzarini, Isonicotinic acid hydrazide derivatives: synthesis, antimicrobial activity, and QSAR studies, Medicinal Chemistry Research, 21, 2012, 1451-1470.
  • D. Kumar, N.M. Kumar, S. Ghosh, K. Shah, Novel bis(indolyl)hydrazide-hydrazones as potent cytotoxic agents, Bioorganic & Medicinal Chemistry Letters, 22, 2012, 212-215.
  • K.S. Kumar, S. Mohanty, G.P. Reddy, V. Siddaiah, J.D. Lilakar, G.L. Goud, Synthesis and Antimicrobial Activity of 3-{2-(1-Aryl-1H-1,2,3-triazol-4-yl)methoxy -5-fluorophenyl}isoxazoles, Russian Journal of General Chemistry, 89, 2019, 1221-1224.
  • S. Kumar, B. Sharma, V. Mehra, V. Kumar, Recent accomplishments on the synthetic/biological facets of pharmacologically active 1H-1,2,3-triazoles, European Journal of Medicinal Chemistry, 212, 2021, 113069.
  • S. Gallagher, M. Hashemzadeh, L.R. Peyton, Triazole antifungals: A review. Drugs Today, 51, 2015,705-718.
  • H. H. Renate, M. G. Eric, L. Carmen, J. S. Peter, W. Baojie, G. F. Scott, G. Jiri, J. R. Philip, C. Kelly, Synthesis, antimalarial and antitubercular activity of acetylenic chalcones, Bioorganic & Medicinal Chemistry Letters, 20, 2010, 942-944.
  • M. Cuendet, K. Hostettmann, O. Potterat, W. Dyatmiko, Iridoid Glucosides with Free Radical Scavenging Properties from Fagraea blumei, Helv Chim Acta, 80, 1997, 1144-1152. I.F. Benzie, J.J. Strain, The ferric reducing ability of plasma (FRAP) as a measure of "antioxidant power": the FRAP assay, Anal Biochem, 239, 1996, 70-76.
  • F. Çelik, Y. Ünver, B. Barut, A. Özel, K. Sancak, Synthesis, Characterization and Biological Activities of New Symmetric Bis-1,2,3-Triazoles with Click Chemistry, Medicinal Chemistry, 14, 2018, 230-241.

New 1H-1,2,3-triazole derivatives: Synthesis, Characterization and Antioxidant Activity

Yıl 2025, Cilt: 7 Sayı: 2, 191 - 194, 31.05.2025
https://doi.org/10.51435/turkjac.1681862

Öz

4-bromo-N-(4-((1-(4-bromobenzyl)-1H-1,2,3-triazol-4-yl)methoxy)-3-methoxy benzylidene) aniline (3), 2-((1-(3-(1,3-dioxoisoindolin-2-yl) propyl)-1H-1,2,3-triazol-4-yl)methoxy) benzaldehyde (6), and 4-((1-(3-(1,3-dioxoisoindolin-2-yl)propyl) -1H-1,2,3-triazol-4-yl)methoxy)-3-methoxyben zaldehyde (8) were synthesized. The compounds were characterized by FTIR, 1H-NMR and 13C-NMR spectroscopic methods. The antioxidant properties of the compounds were evaluated using two widely accepted methodologies assays (DPPH and FRAP). Compound 3 has the highest antioxidant potential among the compounds.

Kaynakça

  • F. Çelik, Y. Ünver, B. Barut, A. Özel, K. Sancak, Synthesis, Characterization and Biological Activities of New Symmetric Bis-1,2,3-Triazoles with Click Chemistry, Medicinal Chemistry, 2018, 230-241.
  • E. Düğdü, D. Ünlüer, F. Çelik, K. Sancak, Ş. A. Karaoğlu, A. Özel, Synthesis of Novel Symmetrical 1,4-Disubstituted 1,2,3-Bistriazole Derivatives via ‘Click Chemistry’ and Their Biological Evaluation, Molecules, 21, 2019, 659-672.
  • F. Çelik, F. Türkan, A. Aras, M. N. Atalar, H. S. Karaman, Y. Ünver, N. Kahriman, Synthesis of novel 1,2,3 Triazole Derivatives and Assessment of Their Potential Cholinesterases, Glutathione S-transferase Enzymes Inhibitory Properties: An in Vitro and in Silico Study, Bioorganic Chemistry, 107, 2021.
  • R. P. Frutos, S. Rodriguez, N. D. Patel, D. Reeves, T. Tampone, C.H. Senanayake, A General and Practical Synthesis of N-Aryl-3- 4-(imidazol-4-yl)-1,2,3-triazol-1-yl benzamide Anti-Inflammatory Cytokine Inhibitors, Asian Journal of Organic Chemistry, 3, 2014, 769-772.
  • R. Jain, P. Gahlyan, S. Dwivedi, R. Konwar, S. Kumar, M. Bhandari, R. Arora, R. Kakkar, R. Kumar, A.K. Prasad, Design, Synthesis and Evaluation of 1H-1,2,3-Triazol-4-yl-methyl Tethered 3-Pyrrolylisatins as Potent Anti-Breast Cancer Agents, Chemistry Select, 19, 2018, 5263-5268.
  • D. L. Jardim, M. Schwaederle, D. S. Hong, R. Kurzrock, An appraisal of drug development timelines in the Era of precision oncology, Oncotarget, 7, 2016, 53037-53046.
  • V. Judge, B. Narasimhan, M. Ahuja, D. Sriram, P. Yogeeswari, Isonicotinic Acid Hydrazide Derivatives: Synthesis, Antimycobacterial, Antiviral, Antimicrobial Activity and QSAR Studies, Letters in Drug Design & Discovery, 8, 2011, 792-810.
  • V. Judge, B. Narasimhan, M. Ahuja, D. Sriram, P. Yogeeswari, E. De Clercq, C. Pannecouque, J. Balzarini, Isonicotinic acid hydrazide derivatives: synthesis, antimicrobial activity, and QSAR studies, Medicinal Chemistry Research, 21, 2012, 1451-1470.
  • D. Kumar, N.M. Kumar, S. Ghosh, K. Shah, Novel bis(indolyl)hydrazide-hydrazones as potent cytotoxic agents, Bioorganic & Medicinal Chemistry Letters, 22, 2012, 212-215.
  • K.S. Kumar, S. Mohanty, G.P. Reddy, V. Siddaiah, J.D. Lilakar, G.L. Goud, Synthesis and Antimicrobial Activity of 3-{2-(1-Aryl-1H-1,2,3-triazol-4-yl)methoxy -5-fluorophenyl}isoxazoles, Russian Journal of General Chemistry, 89, 2019, 1221-1224.
  • S. Kumar, B. Sharma, V. Mehra, V. Kumar, Recent accomplishments on the synthetic/biological facets of pharmacologically active 1H-1,2,3-triazoles, European Journal of Medicinal Chemistry, 212, 2021, 113069.
  • S. Gallagher, M. Hashemzadeh, L.R. Peyton, Triazole antifungals: A review. Drugs Today, 51, 2015,705-718.
  • H. H. Renate, M. G. Eric, L. Carmen, J. S. Peter, W. Baojie, G. F. Scott, G. Jiri, J. R. Philip, C. Kelly, Synthesis, antimalarial and antitubercular activity of acetylenic chalcones, Bioorganic & Medicinal Chemistry Letters, 20, 2010, 942-944.
  • M. Cuendet, K. Hostettmann, O. Potterat, W. Dyatmiko, Iridoid Glucosides with Free Radical Scavenging Properties from Fagraea blumei, Helv Chim Acta, 80, 1997, 1144-1152. I.F. Benzie, J.J. Strain, The ferric reducing ability of plasma (FRAP) as a measure of "antioxidant power": the FRAP assay, Anal Biochem, 239, 1996, 70-76.
  • F. Çelik, Y. Ünver, B. Barut, A. Özel, K. Sancak, Synthesis, Characterization and Biological Activities of New Symmetric Bis-1,2,3-Triazoles with Click Chemistry, Medicinal Chemistry, 14, 2018, 230-241.
Toplam 15 adet kaynakça vardır.

Ayrıntılar

Birincil Dil İngilizce
Konular Tıbbi ve Biyomoleküler Kimya (Diğer)
Bölüm Research Articles
Yazarlar

Fatih Çelik 0000-0001-5510-3494

Yayımlanma Tarihi 31 Mayıs 2025
Gönderilme Tarihi 22 Nisan 2025
Kabul Tarihi 21 Mayıs 2025
Yayımlandığı Sayı Yıl 2025 Cilt: 7 Sayı: 2

Kaynak Göster

APA Çelik, F. (2025). New 1H-1,2,3-triazole derivatives: Synthesis, Characterization and Antioxidant Activity. Turkish Journal of Analytical Chemistry, 7(2), 191-194. https://doi.org/10.51435/turkjac.1681862
AMA Çelik F. New 1H-1,2,3-triazole derivatives: Synthesis, Characterization and Antioxidant Activity. TurkJAC. Mayıs 2025;7(2):191-194. doi:10.51435/turkjac.1681862
Chicago Çelik, Fatih. “New 1H-1,2,3-triazole derivatives: Synthesis, Characterization and Antioxidant Activity”. Turkish Journal of Analytical Chemistry 7, sy. 2 (Mayıs 2025): 191-94. https://doi.org/10.51435/turkjac.1681862.
EndNote Çelik F (01 Mayıs 2025) New 1H-1,2,3-triazole derivatives: Synthesis, Characterization and Antioxidant Activity. Turkish Journal of Analytical Chemistry 7 2 191–194.
IEEE F. Çelik, “New 1H-1,2,3-triazole derivatives: Synthesis, Characterization and Antioxidant Activity”, TurkJAC, c. 7, sy. 2, ss. 191–194, 2025, doi: 10.51435/turkjac.1681862.
ISNAD Çelik, Fatih. “New 1H-1,2,3-triazole derivatives: Synthesis, Characterization and Antioxidant Activity”. Turkish Journal of Analytical Chemistry 7/2 (Mayıs2025), 191-194. https://doi.org/10.51435/turkjac.1681862.
JAMA Çelik F. New 1H-1,2,3-triazole derivatives: Synthesis, Characterization and Antioxidant Activity. TurkJAC. 2025;7:191–194.
MLA Çelik, Fatih. “New 1H-1,2,3-triazole derivatives: Synthesis, Characterization and Antioxidant Activity”. Turkish Journal of Analytical Chemistry, c. 7, sy. 2, 2025, ss. 191-4, doi:10.51435/turkjac.1681862.
Vancouver Çelik F. New 1H-1,2,3-triazole derivatives: Synthesis, Characterization and Antioxidant Activity. TurkJAC. 2025;7(2):191-4.