Synthesis of new 1,2,4-triazole compounds containing Schiff and Mannich bases (morpholine) with antioxidant and antimicrobial activities

Abstract

Compound 2 was synthesized by reacting CS 2 /KOH with compound 1. The treatment of compound 2 with hydrazine hydrate produced compound 3. Then, compound 3 was converted to Schiff bases (4a-d) by the handling with several aromatic aldehydes. The treatment of triazole compounds 4a-d containing Schiff base with morpholine gave compounds 5a-d. All compounds were tested for their antioxidant and antimicrobial activities. The antioxidant test results of DPPH radical scavenging and ferric reducing/antioxidant power methods showed good antioxidant activity. The triazole-thiol (3) was the most active, and the effect of the substituent type of the thiophene ring on the activity was same for both Schiff bases (4a-d) and Mannich bases (5a-d). Among the newly synthesized triazole derivatives, the Schiff base 4d and the Mannich base 5d carrying nitro substituent on the thiophene ring showed promising antibacterial and antifungal activity, with lower MIC values than the standard antibacterial ampicillin.

Synthesis, DNA Binding, and Molecular Docking Studies of Dimethylaminobenzaldehyde-Based Bioactive Schiff Bases

“…e signal due to -CH�N appears in the range of 8.5-9.5 ppm for the compounds corresponding to azomethine group which confirms the formation of Schiff bases. Moreover, a peak appears in 3.01-3.13 ppm range attributed to the -CH 3 (6H) aliphatic for the compounds (1)(2)(3)(4)(5)(6)(7)(8). A signal at δ 1.80-2.20 ppm may be assigned to the protons of the (C-CH 2 -C, 8H) for the compounds 2,3, (C-CH 2 -C, 10H) for the compounds 4, 5, and (C-CH 2 -C, 2H) for the compounds 6-8.…”

“…Due to their applications in biological, analytical, and medicinal field, and their role as catalysts in organic synthesis, heterocyclic Schiff bases are considered as one of the most potential groups of heterocyclic compounds [5]. e presence of azomethine group in heterocyclic Schiff base derivatives makes it very critical for various biological applications such as antifungal [6,7], antibacterial [8,9], antiproliferative [10], anticoagulant [11], anti-inflammatory [12], and antiviral [13] agents. ey have been widely used in coordination chemistry mainly due to their facile synthesis, electronic properties, and good solubility in common solvents [14].…”

“…In addition, in this work, we calculated some molecular docking parameters of compounds in order to correlate them with their antimicrobial activity. (1)(2)(3)(4)(5)(6)(7)(8).…”

1,2,4-triazole derivatives with morpholine; DFT study and antileishmanial activity

“…Harmonic vibrational frequencies (scaled with 0.9619 [26]), GIAO 1 H and 13 C chemical shift values (regarding TMS) of compounds I and II by employing DFT/B3LYP/6-311G(d,p) method and experimental results obtained from literature [12] are presented in Tables 2 and 3, respectively. Calculated vibrations and chemical shift values are generally consistent with experimental data.…”

“…triazole derivatives with morpholine; 4-((3-methyl thiophene-2-yl)methylenamino)-1-((4-(3methylthiophene-2-yl)methyleneamino)-1-(morpholinomethyl)-5-thioxo-4,5-dihydro-1H-1,2,4-triazole-3yl)methyl)-3-(thiophene-2-ylmethyl)-1H-1,2,4-triazole-5(4H)-one (I) and 1-((1-(morpholinomethyl)-4-(5nitrothiophene-2-yl)methyleneamino)-5-thioxo-4,5-dihydro-1H-1,2,4-triazole-3-yl)methyl)-4-((5nitrothiophene-2-yl)methylene amino)-3-(thiophene-2-ylmethyl)-1H-1,2,4-triazole-5(4H)-one (II) were published in literature[12]. The structures of the compounds I and II are showed in Scheme 1.…”