An insight on medicinal attributes of 1,2,3‐ and 1,2,4‐triazole derivatives as alpha-amylase and alpha-glucosidase inhibitors

Sharma, Anushka; Dubey, Rahul; Bhupal, Ritu; Patel, Preeti; Verma, Sant Kumar; Kaya, Savas; Asati, Vivek

doi:10.1007/s11030-023-10728-1

Cited by 9 publications

(2 citation statements)

References 61 publications

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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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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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“…Several contemporary drugs, including antifungals like fluconazole, voriconazole, and itraconazole, anti-convulsant like alprazolam, and anti-viral like ribavirin, feature the 1,2,4-triazole scaffold. [5] Moreover, derivatives containing the latter moiety are recognized for their diverse biological activities, spanning antidiabetic, [6][7][8] α-glucosidase inhibition, [9][10][11] antibacterial, [12] antifungal, [13] antimalarial, [14] antiviral, [15] and antispasmodic properties. [16] Some of these compounds, which were derived from 1,2,4-triazole, also display moderate to good effects as antiproliferative, [17] antioxidant, [18] and anticancer agent.…”

Section: Introductionmentioning

confidence: 99%

Studying the Structure and Evaluating α‐Glucosidase Inhibition of Novel Acetamide Derivatives Incorporating 4‐Ethyl‐4H‐1,2,4‐Triazole Starting from 2‐(Naphthalen‐1‐yl)Acetic Acid

Le,

Nguyen,

Tran

et al. 2024

Asian J Org Chem

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This research aims to create innovative compounds that incorporate 1,2,4‐triazole and exhibit α‐glucosidase inhibitory potential. Similar to our previously reported series of N‐aryl 2‐{[5‐(naphthalen‐1‐ylmethyl)‐4‐phenyl‐4H‐1,2,4‐triazol‐3‐yl]thio}acetamide compounds, we explore here 4‐ethyl instead of 4‐phenyl as substituent. The synthesis process effectively yielded these compounds, with the highest yield reaching up to 91% for compound N‐phenyl‐2‐{[5‐(naphthalen‐1‐ylmethyl)‐4‐ethyl‐4H‐1,2,4‐triazol‐3‐yl]thio}acetamide 5a. Their structures were validated through various spectroscopic techniques such as IR, 1H‐NMR, 13C‐NMR, and HR‐MS spectra, and for compounds 3, 5d, and 5e by X‐ray diffraction. In vitro experiments revealed that only compound 5g, marked by a 3‐hydroxy substitution on the N‐phenylacetamide moiety, demonstrated higher α‐glucosidase inhibitory potential (IC50 = 158.4 ± 3.4 μM) compared to the positive control, acarbose (IC50 = 351.3 ± 1.8 μM). Molecular docking studies also coincide with in vitro assay by uncovering a strong hydrogen bond with residue Asp1526 along with other hydrophobic interactions of compound 5g in the α‐glucosidase binding pocket. Compound 5g showed a free binding energy of ‐9.7 kcal/mol, contrasting with acarbose (‐8.0 kcal/mol). Despite the modest activity, this research underscores the simplicity and convenience of the procedure for synthesizing 1,2,4‐triazole‐based compounds, and contributes a key feature to the structure‐activity relationship of the triazole scaffold in the α‐glucosidase pocket.

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Synthesis and biological evaluation of indole derivatives containing thiazolidine-2,4-dione as α-glucosidase inhibitors with antidiabetic activity

Hu,

Liang,

Sun

et al. 2024

European Journal of Medicinal Chemistry

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An insight on medicinal attributes of 1,2,3‐ and 1,2,4‐triazole derivatives as alpha-amylase and alpha-glucosidase inhibitors

Cited by 9 publications

References 61 publications

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

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

Studying the Structure and Evaluating α‐Glucosidase Inhibition of Novel Acetamide Derivatives Incorporating 4‐Ethyl‐4H‐1,2,4‐Triazole Starting from 2‐(Naphthalen‐1‐yl)Acetic Acid

Synthesis and biological evaluation of indole derivatives containing thiazolidine-2,4-dione as α-glucosidase inhibitors with antidiabetic activity

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