| Türkçe Özet |
Bu çalışmada, öncelikle çalışma için gerekli olan 8 adet 3-alkil/aril-4-amino-4,5-dihidro-1H-1,2,4-triazol-5-on bileşiği sentezlenmiş ve ayrı ayrı salisilaldehit (2-hidroksibenzaldehit) ile muamele edilerek beş tanesi literatürde kayıtlı 8 adet 3-alkil(aril)-4-(2-hidroksibenzilidenamino)-4,5-dihidro-1H-1,2,4-triazol-5-on (4) bileşikleri elde edilmiştir. Çalışmanın devamında Mannich reaksiyonu uyarınca formaldehit varlığında morfolin, 2,6-dimetilmorfolin, 3-metilpiperidin, 4-piperidinkarboksamid, 1-metilpiperazin, etil 1-piperazinkarboksilat(1-etoksikorbonilpiparazin) ve piperazin ile muamele edilerek sırasıyla 8'er adet yeni 5 tipi 1-(morfolin-4-il-metil)-3-alkil(aril)-4-(2-hidroksibenzilidenamino)-4,5-dihidro-1H-1,2,4-triazol-5-on, 14 tipi 1-(2,6-dimetilmorfolin-4-il-metil)-3-alkil(aril)-4-(2-hidroksibenzilidenamino)-4,5-dihidro-1H-1,2,4-triazol-5-on, 23 tipi 1-(3-metilpiperidin-1-il-metil)-3-alkil(aril)-4-(2-hidroksibenzilidenamino)-4,5-dihidro-1H-1,2,4-triazol-5-on, 32 tipi 1-(4-piperidinkarboksamid-1-il-metil)-3-alkil(aril)-4-(2-hidroksibenzilidenamino)-4,5-dihidro-1H-1,2,4-triazol-5-on, 41 tipi 1-(4-metilpiperazin-1-il-metil)-3-alkil(aril)-4-(2-hidroksibenzilidenamino)-4,5-dihidro-1H-1,2,4-triazol-5-on, 50 tipi 1-(4-etoksikarbonilpiparazin-1-il-metil)-3-alkil(aril)-4-(2-hidroksibenzilidenamino)-4,5-dihidro-1H-1,2,4-triazol-5-on ve 59 tipi N,N'-Bis-[3-alkil(aril)-4-(2-hidroksibenziliden amino)-4,5-dihidro-1H-1,2,4-triazol-5-on-1-il-metil]-piperazin bileşikleri sentezlenmiş olup toplam 56 adet heterosiklik yeni N-Mannich bazı elde edilmiştir.İkinci bölümde sentezlenen toplam 56 yeni bileşiğin yapıları IR, 1H-NMR ve 13C-NMR spektroskopik yöntemleri kullanılarak aydınlatılmıştır.Çalışmanın üçüncü bölümünde, yeni bileşikler biri mantar olmak üzere toplam 7 farklı mikroorganizmaya karşı Bs (Bacillus subtilis, ATCC-11774), Bc (Bacillus cereus, ATCC 11778), Pa (Pseudomonas aeruginosa, ATTC 27853), Kp (Klebsiella pneumonia, ATCC 4352), Sa (Staphylococcus aureus, ATCC 6538), Ec (Escherichia coli ATCC 25922), Ca (Candida Albicans, ATCC 60193) agar kuyucuk difüzyon yöntemi ile antimikrobiyal ve antifungal özellikleri araştırılmış ve elde edilen sonuçlar değerlendirilmiştir.Çalışmanın dördüncü bölümünde, sentezlenen yeni heterosiklik bileşiklerin üç farklı yöntemle (indirgeme gücü, serbest radikal giderme aktivitesi ve metal şelat aktivitesi) in-vitro antioksidan değerlendirmeleri yapılmış ve elde edilen sonuçlar tartışılmıştır. |
| İlgilizce Özet |
In this study, eight 3-alkyl(aryl)-4-amino-4,5-dihydro-1H-1,2,4-triazol-5-one compounds were initially synthesized. These compounds were individually reacted with salicylaldehyde (2-hydroxybenzaldehyde) to obtain eight known Schiff base derivatives: 3-alkyl(aryl)-4-(2-hydroxybenzylideneamino)-4,5-dihydro-1H-1,2,4-triazol-5-one (4). In the next stage, these Schiff base compounds were subjected to Mannich reactions in the presence of formaldehyde and seven different 2° amine compounds morpholine, 2,6-dimethylmorpholine, 3-methylpiperidine, 4-piperidinecarboxamide, 1-methylpiperazine, ethyl 1-piperazinecarboxylate and piperazine, and 5-type eight novel 1-(morpholin-4-yl-methyl)-3-alkyl(aryl)-4-(2-hydroxybenzylideneamino)-4,5-dihydro-1H-1,2,4-triazol-5-one, 14-type eight novel 1-(2,6-dimethylmorpholin-4-yl-methyl)-3-alkyl(aryl)-4-(2-hydroxybenzylideneamino)-4,5-dihydro-1H-1,2,4-triazol-5-one, 23 type eight novel 1-(3-methylpiperidin-1-yl-methyl)-3-alkyl(aryl)-4-(2-hydroxybenzylideneamino)-4,5-dihydro-1H-1,2,4-triazol-5-one, 32 type eight novel 1-(4-piperidinecarboxyamide-1-yl-methyl)-3-alkyl(aryl)-4-(2-hydroxybenzylideneamino)-4,5-dihydro-1H-1,2,4-triazol-5-one, 41 type eight novel 1-(4-methylpiperazin-1-yl-methyl)-3-alkyl(aryl)-4-(2-hydroxybenzylideneamino)-4,5-dihydro-1H-1,2,4-triazol-5-one, 50 type eight novel 1-(ethyl-1-piperazinecarboxyamide-1-yl-methyl)-3-alkyl(aryl)-4-(2-hydroxybenzylideneamino)-4,5-dihydro-1H-1,2,4-triazol-5-one and 59 type eight novel N,N'-Bis-[3-alkyl(aryl)-4-(2-hydroxybenzylidene amino)-4,5-dihydro-1H-1,2,4-triazol-5-one-1-yl-methyl]-piperazines were obtained. In the second part of the study, the structures of all 56 compounds synthesized were elucidated using spectroscopic techniques such as infrared (IR) spectroscopy, proton nuclear magnetic resonance (¹H-NMR) and carbon-13 nuclear magnetic resonance (¹³C-NMR). In the third part, the antimicrobial activities of these compounds were evaluated using the agar well diffusion method against seven different microorganisms: Bacillus subtilis (ATCC 11774), Bacillus cereus (ATCC 11778), Pseudomonas aeruginosa (ATCC 27853), Klebsiella pneumoniae (ATCC 4352), Staphylococcus aureus (ATCC 6538), Escherichia coli (ATCC 25922), and Candida albicans (ATCC 60193). The antimicrobial test results were analyzed and compared.In the final part of the study, in-vitro antioxidant activities of the synthesized compounds were investigated using three different methods: reducing power assay, free radical scavenging activity (DPPH assay), and metal chelation activity. The obtained data were discussed in detail with regard to their potential biological significance and structure–activity relationships.Keywords: 1,2,4-t-Triazol-5-one, Schiff base, Mannich base, antioxidant activity, antimicrobial activit. |
