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

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...

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Bibliographic Details
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
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Summary: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.
ISSN:1735-207X
1735-2428
DOI:10.1007/s13738-021-02386-7