Current development of 1,2,3-triazole derived potential antimalarial scaffolds: Structure- activity relationship (SAR) and bioactive compounds

Rahman, Sudarman; Bhatti, Jasvinder Singh; Thareja, Suresh; Monga, Vikramdeep

doi:10.1016/j.ejmech.2023.115699

Cited by 24 publications

(3 citation statements)

References 114 publications

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“…[37] Several triazole-based hybrids and conjugates have demonstrated potential antimalarial activity. [38,39] Molecular hybridization is a method for rationally designing various prototypes that recognizes pharmacophoric subunits in two or more known bioactive derivatives. Consequently, hybrid architectures can be developed that retain the potency of the original templates.…”

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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“…Furthermore, thiazolidinic derivatives have been successfully applied in organocatalytic asymmetric direct aldol addition [19][20][21] and as chiral ionic liquids to produce chiral secondary alcohols with excellent enantiomeric excesses. [22] In parallel with the interest in thiazolidines, the study of 1,2,3-triazoles has also gained prominence for similar reasons: their diverse applications, both in pharmacology [23][24][25] and materials science. [26][27][28] In recent years, our research group has focused on the synthesis of novel molecules containing the 1,2,3-triazole unit and assessing their biological properties to explore new avenues for their utilization.…”

Section: Introductionmentioning

confidence: 99%

Organocatalytic Synthesis and DNA Interactive Studies of New 1,2,3‐triazolyl‐thiazolidines Hybrids

Larroza,

Soares,

Morais

et al. 2024

ChemBioChem

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An organocatalytic [3 + 2] cycloaddition reaction between thiazolidine‐containing β‐ketoester 1 and aryl azides 2 was employed to synthesize new 1,2,3‐triazolyl‐thiazolidine hybrids 3. In this metal‐free approach, twelve compounds were isolated in yields ranging from 23% to 96% by using diethylamine (10 mol%) and DMSO at 75 °C for 24 hours. DNA‐binding assays were conducted through absorption, emission spectroscopy and viscosimetry analysis, to evaluate the interaction capacity of the studied derivatives with nucleic acids. All the synthesized compounds were evaluated for their interactions with a specific group of compounds containing the pharmacophoric groups triazole and thiazolidine through a molecular docking speculative study, aimed at identifying the interaction profile of these compounds with DNA. The obtained results suggest that 1,2,3‐triazolyl‐thiazolidine hybrids could be a promising approach in the development of novel therapeutic agents targeting DNA‐related processes.

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“…It is always imperative to design and synthesize new molecules of such useful N ‐heterocyclic compounds required for the applications [7,8] . Among these, triazoles, tetrazoles, triazines and tetrazines are very important classes of N ‐heterocyclic compounds and their properties have been extensively studied [9,10] . Various biological applications of a variety of triazole derivatives (Figure 1) have been extensively studied.…”

Section: Introductionmentioning

confidence: 99%

Cu(II)‐Catalyzed Green Synthesis of 1,4,5‐Trisubstituted‐1,2,3‐Triazoles from Chalcone Derivatives – Studies on Their Cytotoxicity Profile

Mondal,

Sivaramakrishna

2024

ChemistrySelect

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Triazoles are an important class of heterocyclic compounds due to their interesting structural features and versatile biological significance. In this regard, the present work highlights the synthesis of Cu(II)‐catalyzed 1,2,3‐trisubstituted triazoles through the cycloaddition of different chalcones with azides under neat methodology. A series of 16 triazole derivatives (3 a to 3 o) was prepared using 10 mol % Cu(II) complexes of 1,10‐phenanthroline and terpyridine‐based ligands as catalysts with moderate to excellent yields. All these derivatives were structurally analyzed by UV‐visible, infrared, 1H, 13C NMR and mass spectral data. The product, (4‐((4‐benzoyl‐5‐(4‐fluorophenyl)‐1H‐1,2,3‐triazol‐1‐yl) methyl)benzonitrile) (3 j) was structurally analyzed by single crystal XRD analysis. Also, the molecular structure of one of the catalysts, [Cu(Phen)2]2+(NO3−)2) was obtained by single crystal XRD analysis. Additional investigations of all these derivatives exhibited potential cytotoxic characteristics against MCF‐7 cancer cell lines. Among them, compounds 3 j, 3 i, 3 c, 3 d and 3 g facilitated the notable IC50 values. Moreover, the studies on the photophysical properties of synthesized derivatives showed the absorption bands in the range of 267–290 nm, depending on the nature of the substituent and the compounds 3 e and 3 f demonstrated the highest and lowest quantum yields as 0.05339 % and 0.01914 %, respectively.

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Current development of 1,2,3-triazole derived potential antimalarial scaffolds: Structure- activity relationship (SAR) and bioactive compounds

Cited by 24 publications

References 114 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

Organocatalytic Synthesis and DNA Interactive Studies of New 1,2,3‐triazolyl‐thiazolidines Hybrids

Cu(II)‐Catalyzed Green Synthesis of 1,4,5‐Trisubstituted‐1,2,3‐Triazoles from Chalcone Derivatives – Studies on Their Cytotoxicity Profile

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