Synthesis of Some New Schiff Bases Containing 1,2,4-Triazole Rings, Investigation of Their In Vitro Biological Activities and Potentiometric Titrations

Yıl 2025, Cilt: 15 Sayı: 4, 1490 - 1503, 15.12.2025

Fevzi Aytemiz , Haydar Yüksek

https://doi.org/10.31466/kfbd.1625879

Öz

In this study, a new 3-formylphenyl 2,5-dichlorobenzenesulfonate compound (2) was synthesized from the reaction of 3-hydroxybenzaldehyde and 2,5-dichlorobenzenesulfonyl chloride in triethylamine medium. The synthesized benzaldehyde derivative compound (2) was put into reaction with nine 3-alkyl/aryl-4-amino-4,5-dihydro-1H-1,2,4-triazol-5-one (1a-1i) compounds registered in the literature. As a result of the reaction, nine new compounds 3-[(3-alkyl/aryl-4,5-dihydro-1H-1,2,4-triazol-5-on-4-yl)-azomethine]-phenyl 2,5-dichlorobenzenesulfonate (3a-3i)) were synthesized. The structures of the synthesized novel Schiff base compounds (3a-3i) were characterized by IR, 1H-NMR, 13C-NMR spectroscopic methods. The biological properties of the new compounds (3a-3i) were investigated by examining both their antibacterial and antioxidant properties. The antibacterial properties were examined by Agar well diffusion method and as a result of the observations, it was determined that compounds 3a-3d, 3h and 3i have antibacterial activity. The antioxidant properties were investigated by Blois, Dinis, Oyaizu methods and it was observed that the synthesized new compounds (3a-3i) have metal chelate activity very close to α-tocopherol used as standard. In addition, the acidic properties of the novel Schiff base compounds (3a-3i) were investigated by titration with tetrabutylammonium hydroxide (TBAH) in four different anhydrous solvents (DMF, isopropyl alcohol, acetone and tert-butyl alcohol) and their semi-neutralization potentials and corresponding pKa values were determined.

Anahtar Kelimeler

1,2,4-Triazole, , Schiff Base , Antibacterial , Antioxidant , Potentiometry

Proje Numarası

2019-FM-09

1,2,4-Triazol Halkası İçeren Bazı Yeni Schiff Bazlarının Sentezi, İn Vitro Biyolojik Aktivitelerinin İncelenmesi ve Potansiyometrik Titrasyonları

Öz

Bu çalışmada, 3-hidroksibenzaldehit ile 2,5-diklorobenzensulfonil klorürün trietilamin ortamındaki reaksiyonundan yeni 3-formilfenil 2,5-diklorobenzensulfonat (2) bileşiği sentezlenmiştir. Sentezlenen benzaldehit türevi bileşik (2) ile literatürde kayıtlı dokuz adet 3-alkil/aril-4-amino-4,5-dihidro-1H-1,2,4-triazol-5-on (1a-1i) bileşikleri reaksiyona sokulmuştur. Reaksiyon sonucunda dokuz adet yeni 3-[(3-alkil/aril-4,5-dihidro-1H-1,2,4-triazol-5-on-4-il)-azometin]-fenil 2,5-diklorobenzensulfonat (3a-3i) bileşikleri sentezlenmiştir. Sentezlenen yeni Schiff bazı bileşiklerin (3a-3i) yapıları IR, 1H-NMR, 13C-NMR spektroskopik yöntemler ile karakterizasyonu yapılmıştır. Yeni bileşiklerin (3a-3i) hem antibakteriyel hem de antioksidan özelliklerine bakılarak biyolojik özellikleri incelenmiştir. Antibakteriyel özellikleri Agar kuyucuk difüzyon metodu ile incelenmiş ve gözlemlemeler sonucunda 3a-3d, 3h ve 3i bileşiklerinin iyi antibakteriyel aktiviteye sahip olduğu belirlenmiştir. Antioksidan özellikleri Blois, Dinis, Oyaizu metotları ile incelenmiş ve sentezlenen yeni bileşiklerin (3a-3i) standart olarak kullanılan α-tokoferole oldukça yakın düzeyde metal şelat aktivitesine sahip olduğu gözlemlenmiştir. Ayrıca, yeni Schiff bazı bileşiklerinin (3a-3i) dört farklı susuz çözücüde (DMF, izopropil alkol, aseton ve tert-butil alkol) tetrabutilamonyum hidroksit (TBAH) ile titre edilerek asidik özelliklerine bakılmış, yarı nötralizasyon potansiyelleri ve bunlara karşılık gelen pKa değerleri belirlenmiştir.

Anahtar Kelimeler

1,2,4-Triazol, , Schiff bazı , Antibakteriyel , Antioksidan , Potansiyometri

Etik Beyan

Yapılan çalışmada araştırma ve yayın etiğine uyulmuştur.

Destekleyen Kurum

Kafkas Üniversitesi Bilimsel Araştırma Projeleri Koordinasyon Birimi

Proje Numarası

2019-FM-09

Teşekkür

Bu çalışma Kafkas Üniversitesi Bilimsel Araştırma Projeleri Koordinasyon Birimine teşekkür ederiz. Ayrıca asitlik çalışmalarında vermiş olduğu katkıdan dolayı Kafkas Üniversitesi, Eğitim Fakültesi öğretim üyesi sayın Doç. Dr. Zafer OCAK’a teşekkür ederiz.

Kaynakça

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