Microwave-promoted synthesis and biological activity of some 2-hetarylmethyl-4-(4-hetarylphenyl)-5-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one derivatives
“…Similarly, Özil et al synthesized 1,2,4-triazole derivatives ( Scheme 26 ) by modifying groups attached to the central benzene ring and N 2 -atom from triazole rings. Of all compounds, derivatives 74 and 75 were the most active [80] . Scheme 26 Chemical structures of 1,2,4-triazole derivatives – potent substances described as urease inhibitor.…”
Section: Organic Substances As Urease Inhibitorsmentioning
“…Similarly, Özil et al synthesized 1,2,4-triazole derivatives ( Scheme 26 ) by modifying groups attached to the central benzene ring and N 2 -atom from triazole rings. Of all compounds, derivatives 74 and 75 were the most active [80] . Scheme 26 Chemical structures of 1,2,4-triazole derivatives – potent substances described as urease inhibitor.…”
Section: Organic Substances As Urease Inhibitorsmentioning
“…After the synthesis of 3 , it was reacted with ethyl bromoacetate under both microwave irradiation and conventional methods and thus ethyl‐4‐[1‐(2‐ethoxy‐2‐oxoethyl) ‐3‐methyl‐5‐oxo‐1,5‐dihydro‐4 H ‐1,2,4‐triazol‐4‐yl]benzoate ( 4 ) was synthesized. Then, compound 4 reacted with an excess of hydrazine hydrate to produce dihydrazide 5 containing two functional groups amenable to simultaneous modification according to the literature …”
Glutathione reductase (GR) is responsible for the existence of the reduced glutathione (GSH) molecule, a crucial antioxidant against oxidative stress reagents. The antimalarial activities of some redox active compounds are attributed to their inhibition of antioxidant flavoenzyme GR, and inhibitors are therefore expected to be useful for the treatment of malaria. In this work, a fast and effective synthesis and the GR inhibitory properties of 5-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one's aryl Schiff base derivatives are reported. For this aim, the triazol nucleus was obtained, which was substituted with identical groups: ester, hydrazide, and Schiff base system at the N-2 and N-4 nitrogen atoms. The majority of the reactions were carried out by utilizing both microwave and conventional methods in order to compare their yields and reaction times. Beside this, the occuring E/Z geometrical isomers from the CN double bond and the cis/trans amide conformers at the CONH single bond were studied. In the biological activity section of this work, it was found that all synthesized compounds have better inhibitory activity than N,N-bis(2-chloroethyl)-N-nitrosourea against GR; especially, two molecules, 6e and 6f, are the best among them. The evidence indicates that these Schiff base derivatives, with triazole ring, are strong GR inhibitors and novel antimalaria candidates.
“…The infrared spectroscopic data of compounds 4 showed the absence of absorption at about the 1200-1100 cm -1 region characteristic of the C═S stretching, and the presence of an S-H stretching band at 2550 cm -1 vibrations showed that these compounds were in the thiol form. [35,41] The structures of the novel compounds were confirmed by mass spectrometry, Fourier-transform infrared (FTIR), 1 H- 13 C NMR (nuclear magnetic resonance) spectroscopy, and elemental analysis. The OH, SH, NH, and NH 2 signals were determined by monitoring the proton exchange in the presence of deuterium oxide (D 2 O).…”
The synthesis, in silico molecular docking, and in vitro urease inhibition studies of a novel series of benzothiazole derivatives are reported. The title compounds in the two series, namely, 2-({5-[(benzothiazol-2-ylthio)methyl]-1,3,4-oxadiazol-2-yl}thio)-1-(4-substitutedphenyl)ethan-1-one and 2-(benzothiazol-2-ylthio)-1-(4-substituted-phenyl)ethan-1-one oxime, were synthesized by the reaction of benzo[d]thiazole-2-thiol with different kinds of intermediates in several steps using both conventional and microwave techniques. All compounds were found to have an excellent degree of ureaseinhibitory potential ranging between 16.16 ± 0.54 and 105.32 ± 2.10 µM when compared with the standard inhibitor acetohydroxamic acid with IC 50 = 320.70 ± 4.24 µM.The structure-activity relationship was established in detail. The binding interactions of the compounds with the enzyme were confirmed through molecular docking.Further, 100 -ns molecular dynamics simulations were performed to investigate the stability and structural perturbations experienced by the most potent compound over the urease active site.
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