Synthesis, characterization and biological activities of N-Mannich bases and amide compounds developed from heterocyclic triazol-5-one derivatives: 3-alkyl(aryl)-4-amino-4,5-dihydro-1H-1,2,4-triazol-5-ones

Öz

Among heterocyclic compounds, 1,2,4-triazoles are valuable chemical structures known for their broad spectrum of biological activities and unique roles in medicinal chemistry applications, especially in drug development processes. In this study, eight 3-alkyl(aryl)-4-amino-4,5-dihydro-1H-1,2,4-triazol-5-one derivatives were synthesized and reacted with 3-nitrobenzoyl chloride to obtain N-[3-alkyl(aryl)-4,5-dihydro-1H-1,2,4-triazol-5-one-4-yl]-3-nitrobenzamide derivatives. Subsequently, the amide derivatives underwent Mannich reactions with formaldehyde and morpholine, resulting in four N-Mannich bases. The structures of a total of 12 synthesized compounds were elucidated using IR, 1H-NMR and 13C-NMR spectroscopic techniques. The biological activities of the compounds were evaluated in vitro. Antioxidant properties were assessed using reducing power, free radical scavenging, and metal chelating activity assays. Additionally, antimicrobial activities were tested against five microorganisms (Bacillus cereus, Klebsiella pneumoniae, Staphylococcus aureus, Serratia marcescens, and Candida albicans) using the agar well diffusion method. The results indicated that the compounds exhibited weak antioxidant activity, while some demonstrated notable antimicrobial effects.

Anahtar Kelimeler

• 4,5-Dihydro-1H-1,2,4-triazol-5-one,
• Amide
• Mannich Base
• Antioxidant Activity
• Antimicrobial Activity

Heterohalkalı triazol-5-on türevlerinden geliştirilen N-Mannich bazı ve amid bileşiklerinin sentezi, karakterizasyonu ve biyolojik aktivitelerinin araştırılması: 3-alkil(aril)-4-amino-4,5-dihidro-1H-1,2,4-triazol-5-on

Öz

Heterosiklik bileşiklerden biri olan 1,2,4-triazoller, ilaç geliştirme sürecinde ve tıbbi kimyada sahip oldukları geniş biyolojik aktivite yelpazesi sayesinde önemli bir kimyasal sınıf oluşturmaktadır. Bu çalışmada, 8 adet 3-alkil(aril)-4-amino-4,5-dihidro-1H-1,2,4-triazol-5-on türevi bileşik, 3-nitrobenzoil klorür ile reaksiyona sokularak N-[3-alkil(aril)-4,5-dihidro-1H-1,2,4-triazol-5-on-4-il]-3-nitrobenzamid türevleri elde edilmiştir. Sonrasında, bu amid türevleri, Mannich reaksiyonuna tabi tutularak formaldehit ve morfolin varlığında dört adet N-Mannich türevi bileşik sentezlenmiştir. Toplamda 12 farklı bileşiğin yapısal özellikleri IR, 1H-NMR ve 13C-NMR spektroskopik yöntemlerle detaylı şekilde incelenmiştir. Elde edilen bileşiklerin biyolojik aktiviteleri in vitro yöntemlerle değerlendirilmiştir. Antioksidan aktiviteleri indirgeme gücü ve serbest radikal temizleme kapasiteleri üzerinden ölçülmüş, ayrıca metal şelatlama testleriyle desteklenmiştir. Antimikrobiyal aktiviteler ise Bacillus cereus, Klebsiella pneumoniae, Staphylococcus aureus, Serratia marcescens ve Candida albicans gibi mikroorganizmalara karşı agar kuyucuk yöntemi kullanılarak test edilmiştir. Sonuçlar, bileşiklerin antioksidan özelliklerinin zayıf olduğunu, ancak belirli bileşiklerin antimikrobiyal etkiler sergilediğini ortaya koymuştur.

Anahtar Kelimeler

• 4,5-Dihidro-1H-1,2,4-triazol-5-on,
• Amid
• Mannich Bazı
• Antioksidan Aktivite
• Antimikrobiyal Aktivite

Kaynakça

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