Some New Hydrazone Derivatives Bearing the 1,2,4-Triazole Moiety as Potential Antimycobacterial Agents

Abstract

Bu çalışma, 1-(4-((2-(4-sübstitüefenil)hidrazono)metil)fenil)-1H-1,2,4-triazol türevlerinin sentezlerini yaparak yapılarını aydınlatmayı ve antimikobakteriyel aktivitelerini incelemeyi amaçlamaktadır. Gereç ve Yöntemler: Bu çalışmada hedef bileşikler (2a-h), 4-(1H-1,2,4-triazol-l-il)benzaldehidin uygun fenilhidrazinlerle kondenzasyonu ile elde edilmiştir. Bileşiklerin yapıları, IR, 1H-NMR ve kütle spektrometrisi ile aydınlatılmıştır. Antimikobakteriyel aktiviteleri, Mycobacterium tuberculosis H37Rv'ye karşı in vitro olarak incelenmiştir. Bulgular: Aktivite sonuçları incelendiğinde, metilsülfonil sübstitüe türevin 2f serinin en aktif üyesi olduğu bulunmuştur. Sonuç: Metilsulfonil sübstitüe türevin dikkate değer antimikobakteriyel aktivite göstermesine rağmen, sentezlenen bileşiklerin hiçbirinin M. tuberculosis'e karşı izoniazit, rifampin, etambutol ve siprofloksazin kadar etkili olmadıkları bulunmuştur. Anahtar kelimeler: Hidrazon, 1,2,4-triazol, antimikobakteriyel aktivite Objectives: The aim of this study was to synthesize, characterize, and screen some new 1-(4-((2-(4-substitutedphenyl)hydrazono)methyl)phenyl)-1H-1,2,4-triazole derivatives for their antimycobacterial activities. Materials and Methods: The target compounds (2a-h) were gained by condensation of 4-(1H-1,2,4-triazol-1-yl)benzaldehyde with appropriate phenylhydrazines. Their structures were elucidated by IR, 1 H-NMR, and mass spectrometry. The antimycobacterial activities of the compounds were determined in vitro against Mycobacterium tuberculosis H37Rv. Results: The biological assay results showed that the methylsulfonyl-substituted derivative 2f displayed the highest antimycobacterial activity in this series. Conclusion: Although the methylsulfonyl-substituted derivative exhibited significant antimycobacterial activity, none of the synthesized compounds was as effective as isoniazid, rifampin, ethambutol, and ciprofloxacin against M. tuberculosis.

Recent advancement in drug development of nitro(NO2)‐heterocyclic compounds as lead scaffolds for the treatment of Mycobacterium tuberculosis

“…New N ‐(2‐phenoxyethyl)imidazo[1,2‐a]pyridine‐3‐carboxamide‐based derivatives ( 1 – 5 ) (Wu et al, 2016). A novel 1‐(4‐((2‐[2,4‐dinitrophenyl]hydrazono)methyl)phenyl)‐1H1,2,4‐triazole analogue ( 6 ) (Özadali Sari et al, 2019)…”

“…Özadali Sari et al (2019) tested a novel 1‐(4‐((2‐[2,4‐dinitrophenyl]hydrazono)methyl)phenyl)‐1 H‐ 1,2,4‐triazole derivative ( 6 ) against Mtb (H 37 Rv). Compound ( 6 ) demonstrated an MIC value of >141.64 μM (H37Rv; Figure 2; Özadali Sari et al, 2019).…”

“…Özadali Sari et al (2019) tested a novel 1‐(4‐((2‐[2,4‐dinitrophenyl]hydrazono)methyl)phenyl)‐1 H‐ 1,2,4‐triazole derivative ( 6 ) against Mtb (H 37 Rv). Compound ( 6 ) demonstrated an MIC value of >141.64 μM (H37Rv; Figure 2; Özadali Sari et al, 2019). Yadav et al (2018) reported novel 2‐(1‐benzoyl‐1 H ‐benzo[d] imidazol‐2‐ylthio)‐ N ‐substituted acetamide derivatives with various biological activities, including anti‐ Mtb (H37Rv), anti‐proliferative (MCF‐7 and HCT116), antibacterial, and anti‐fungal effects ( Staphylococcus aureus , Bacillus cereus , Bacillus subtilis , Salmonella typhi , Escherichia coli , Candida albicans , and Aspergillus niger ; Yadav et al, 2018).…”