Recent advances in 1,2,3- and 1,2,4-triazole hybrids as antimicrobials and their SAR: A critical review

Tian, Guang; Song, Quanlai; Liu, Ziwei; Guo, Jin; Cao, Shuang; Long, Sihui

doi:10.1016/j.ejmech.2023.115603

Cited by 38 publications

(7 citation statements)

References 86 publications

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“…Different studies also confirmed the high potency of triazole and its analogs as anticancer [10][11][12] , anti-microbial 13,14 , anti-inflammatory 15,16 , and anti-melanogenic agents as tyrosinase inhibitors. In this category, triazolebenzoimidazole (Compound F) with IC 50 = 9.42 μM is a good example 17 .…”

mentioning

confidence: 79%

Structure-based development of 3,5-dihydroxybenzoyl-hydrazineylidene as tyrosinase inhibitor; in vitro and in silico study

Bagheri,

Moradi,

Iraji

et al. 2024

Sci Rep

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A series of new analogs of 3,5-dihydroxybenzoyl-hydrazineylidene conjugated to different methoxyphenyl triazole (11a-n) synthesized using click reaction. The structures of all synthesized compounds were characterized by FTIR, 1H, 13C-NMR spectroscopy, and CHO analysis. The tyrosinase inhibitory potential of the synthesized compounds was studied. The newly synthesized scaffolds were found to illustrate the variable degree of the inhibitory profile, and the most potent analog of this series was that one bearing 4-methoxyphenyl moiety, and exhibited an IC50 value of 55.39 ± 4.93 µM. The kinetic study of the most potent derivative reveals a competitive mode of inhibition. Next, molecular docking studies were performed to understand the potent inhibitor's binding mode within the enzyme's binding site. Molecular dynamics simulations were accomplished to further investigate the orientation and binding interaction over time and the stability of the 11m-tyrosinase complex.

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mentioning

confidence: 79%

Structure-based development of 3,5-dihydroxybenzoyl-hydrazineylidene as tyrosinase inhibitor; in vitro and in silico study

Bagheri,

Moradi,

Iraji

et al. 2024

Sci Rep

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“…The diversity of biological profiles of triazoles has made them indispensable in medicinal chemistry. They have developed as potential enzyme inhibitors, [28,29] anti-Alzheimer, [30] anticancer, [31,32] antiviral, [33] antifungal, [34] antibacterial, [35] antidiabetic agents, [36] and etc. [37] Several triazole-based hybrids and conjugates have demonstrated potential antimalarial activity.…”

Section: Introductionmentioning

confidence: 99%

Novel Benzotriazole‐β‐lactam Derivatives as Antimalarial Agents: Design, Synthesis, Biological Evaluation and Molecular Docking Studies

Aye,

Jarrahpour,

Haghighijoo

et al. 2024

Chemistry & Biodiversity

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Many people around the world suffer from malaria, especially in tropical or subtropical regions. While malaria medications have shown success in treating malaria, there is still a problem with resistance to these drugs. Herein, we designed and synthesized some structurally novel benzotriazole‐β‐lactams using 2‐(1H‐benzo[d][1,2,3]triazol‐1‐yl)acetic acid as a key intermediate. To synthesize the target molecules, the ketene‐imine cycloaddition reaction was employed. First, The reaction of 1H‐benzo[d][1,2,3]triazole with 2‐bromoacetic acid in aqueous sodium hydroxide yielded 2‐(1H‐benzo[d][1,2,3]triazol‐1‐yl)acetic acid. Then, the treatment of 2‐(1H‐benzo[d][1,2,3]triazol‐1‐yl)acetic acid with tosyl chloride, triethyl amine, and Schiff base provided new β‐lactams in good to moderate yields..The formation of all cycloadducts was confirmed by elemental analysis, FT‐IR, NMR and mass spectral data. Moreover, X‐ray crystallography was used to determine the relative stereochemistry of 4a compound. The in vitro antimalarial activity test was conducted for each compound against P. falciparum K1. The IC50 values ranged from 5.56 to 25.65 μM. A cytotoxicity profile of the compounds at 200 μM final concentration revealed suitable selectivity of the compounds for malaria treatment. Furthermore, the docking study was carried out for each compound into the P. falciparum dihydrofolate reductase enzyme (PfDHFR) binding site to analyze their possible binding orientation in the active site.

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“…Nitrogen-containing heterocyclic chemistry is the most challenging and fruitful area of anti-infective drugs, among which triazoles are one of the most important heterocyclic compounds due to their excellent pharmacological activities as essential components of all cells and organisms [5,6]. The synthesis and drug screening of triazole compounds have been of great interest.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Antibacterial Activity of Novel Triazolo[4,3-a]pyrazine Derivatives

Hu,

Dong,

et al. 2023

Molecules

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Infectious diseases pose a major challenge to human health, and there is an urgent need to develop new antimicrobial agents with excellent antibacterial activity. A series of novel triazolo[4,3-a]pyrazine derivatives were synthesized and their structures were characterized using various techniques, such as melting point, 1H and 13C nuclear magnetic resonance spectroscopy, mass spectrometry, and elemental analysis. All the synthesized compounds were evaluated for in vitro antibacterial activity using the microbroth dilution method. Among all the tested compounds, some showed moderate to good antibacterial activities against both Gram-positive Staphylococcus aureus and Gram-negative Escherichia coli strains. In particular, compound 2e exhibited superior antibacterial activities (MICs: 32 μg/mL against Staphylococcus aureus and 16 μg/mL against Escherichia coli), which was comparable to the first-line antibacterial agent ampicillin. In addition, the structure–activity relationship of the triazolo[4,3-a]pyrazine derivatives was preliminarily investigated.

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Recent advances in 1,2,3- and 1,2,4-triazole hybrids as antimicrobials and their SAR: A critical review

Cited by 38 publications

References 86 publications

Structure-based development of 3,5-dihydroxybenzoyl-hydrazineylidene as tyrosinase inhibitor; in vitro and in silico study

Structure-based development of 3,5-dihydroxybenzoyl-hydrazineylidene as tyrosinase inhibitor; in vitro and in silico study

Novel Benzotriazole‐β‐lactam Derivatives as Antimalarial Agents: Design, Synthesis, Biological Evaluation and Molecular Docking Studies

Synthesis and Antibacterial Activity of Novel Triazolo[4,3-a]pyrazine Derivatives

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