Synthesis and in vitro antioxidant and antimicrobial activities of novel 3-alkyl(aryl)-4-[3-methoxy-4-(2-furylcarbonyloxy)-benzylidenamino]-4,5-dihydro-1H-1,2,4-triazol-5-ones, and their N-acetyl, N-Mannich base derivatives

• Published in: Journal of the Iranian Chemical Society 2022-04, Vol.19 (4), p.1347-1368
• Main Author: Manap, Sevda
• Format: Article
• Language: English
• Subjects: Analytical Chemistry; Antioxidants; Aromatic compounds; Benzaldehyde; Biochemistry; Chemical synthesis; Chemistry; Chemistry and Materials Science; Inorganic Chemistry; Morpholine; NMR; Nuclear magnetic resonance; Organic Chemistry; Original Paper; Physical Chemistry; Piperidine
• ISSN: 1735-207X; 1735-2428
• DOI: 10.1007/s13738-021-02386-7

The reactions of 3-alkyl(aryl)-4-amino-4,5-dihydro-1 H -1,2,4-triazol-5-ones ( 1 ) with 3-methoxy-4-(2-furylcarbonyloxy)-benzaldehyde ( 2 ) formed 3-alkyl(aryl)-4-[3-methoxy-4-(2-furylcarbonyloxy)-benzylidenamino]-4,5-dihydro-1 H -1,2,4-triazol-5-ones (3) . Moreover, their five N -acetyl derivatives were synthesized. Besides, 1-(morpholine-4-yl-methyl)-3-alkyl(aryl)-4-[3-methoxy-4-(2-furylcarbonyloxy)-benzylidenamino]-4,5-dihydro-1 H -1,2,4-triazol-5-ones (5) /1-(4-methylpiperazin-1-yl-methyl)-3-alkyl(aryl)-4-[3-methoxy-4-(2-furylcarbonyloxy)-benzylidenamino]-4,5-dihydro-1 H -1,2,4-triazol-5-ones (6)/ 1-(piperidine-4-carboxyamide-1-yl-methyl)-3-alkyl(aryl)-4-[3-methoxy-4-(2-furylcarbonyloxy)-benzylidenamino]-4,5-dihydro-1 H -1,2,4-triazol-5-ones (7) / N,N ′-bis-{3-alkyl(aryl)-4-[3-methoxy-4-(2-furylcarbonyloxy)-benzylideneamino]-4,5-dihydro-1 H -1,2,4-triazol-5-on-1-yl-methyl}-piperazines (8) were obtained by Mannich reaction between compounds 3 and morpholine/N-methylpiperazine/piperidine-4-carboxyamide/piperazine in the presence of formaldehyde. The newly obtained thirty-four compounds were characterized from IR, 1 H NMR, 13 C NMR, and MS spectral data. Also, these compounds were evaluated for their in vitro antioxidant activity. Furthermore, in vitro antibacterial activity of the compounds was screened against six bacteria.