Convenient synthesis, antimalarial and antimicrobial potential of thioethereal 1,4-disubstituted 1,2,3-triazoles with ester functionality

Kaushik, C. P.; Pahwa, Ashima

doi:10.1007/s00044-017-2072-x

Cited by 41 publications

(10 citation statements)

References 34 publications

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“…Several microbes (bacterial and fungal strains) including S. epidermidis, B. subtilis, P. aeruginosa, E. coli, C. albicans, and A. niger were selected to analyse the inhibitory activity of 1,4-disubstituted 1,2,3triazole scaffolds. 99 The synthesised compound 65 (Fig. 7) displayed equal antimicrobial activity on all selected strains (MIC = 0.0153 µmol/mL) except for A. niger, while another lead derivative 66 (Fig.…”

Section: Antimicrobial Activitymentioning

confidence: 96%

1,2,3-Triazole-containing hybrids as leads in medicinal chemistry: A recent overview

Bozorov

Zhao

Aisa

2019

Bioorganic & Medicinal Chemistry

614

289

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A B S T R A C TThe 1,2,3-triazole ring is a major pharmacophore system among nitrogen-containing heterocycles. These fivemembered heterocyclic motifs with three nitrogen heteroatoms can be prepared easily using 'click' chemistry with copper-or ruthenium-catalysed azide-alkyne cycloaddition reactions. Recently, the 'linker' property of 1,2,3-triazoles was demonstrated, and a novel class of 1,2,3-triazole-containing hybrids and conjugates was synthesised and evaluated as lead compounds for diverse biological targets. These lead compounds have been demonstrated as anticancer, antimicrobial, anti-tubercular, antiviral, antidiabetic, antimalarial, anti-leishmanial, and neuroprotective agents. The present review summarises advances in lead compounds of 1,2,3-triazolecontaining hybrids, conjugates, and their related heterocycles in medicinal chemistry published in 2018. This review will be useful to scientists in research fields of organic synthesis, medicinal chemistry, phytochemistry, and pharmacology. Chemistry: synthesis and properties of the 1,2,3-triazolesThe general synthetic route of 1,2,3-triazoles using click chemistry is described in Scheme 1A. The most popular route to 1,2,3-triazoles is Cu(I)-catalysed Huisgen 1,3-dipolar cycloaddition, which is the https://doi.

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Section: Antimicrobial Activitymentioning

confidence: 96%

1,2,3-Triazole-containing hybrids as leads in medicinal chemistry: A recent overview

Bozorov

Zhao

Aisa

2019

Bioorganic & Medicinal Chemistry

614

289

View full text Add to dashboard Cite

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“…Compound containing 1,2,4-triazine nucleus XI has been reported to possess better antimicrobial activity with less toxicity than ciprofloxacin 30 . The derivative bearing 1,2,3-triazole scaffold XIIa displayed overall encouraging efficiency against all screened microbial strains except Aspergillus niger, while the other derivative XIIb exhibited better antimicrobial potency against all strains except Bacillus subtilis and Aspergillus niger 31 .…”

Section: Introductionmentioning

confidence: 98%

Novel heterocyclic hybrids of pyrazole targeting dihydrofolate reductase: design, biological evaluation and in silico studies

Othman

Gad‐Elkareem

Amr

et al. 2020

Journal of Enzyme Inhibition and Medicinal Chemistry

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A novel series of pyrazole analogues including hydrazones, pyrazolo[4,3-c]-pyridazines, pyrazolo[3,4e][1,2,4]triazine and pyrazolo[3,4-d][1,2,3]triazoles was designed, synthesised and screened for their in vitro antimicrobial and DHFR inhibition activity. Compounds bearing benzenesulphonamide moiety incorporated with 3-methyl-5-oxo-1H-pyrazol-4(5H)-ylidene) hydrazine 3a or 6-amino-7-cyano-3-methyl-5H-pyrazolo[4,3-c]pyridazine 6a revealed excellent and broad spectrum antimicrobial activity comparable to ciprofloxacin and amphotericin B as positive antibiotic and antifungal controls, respectively. Furthermore, these derivatives proved to be the most active DHFR inhibitors with IC 50 values 0.11 ± 1.05 and 0.09 ± 0.91 mM, in comparison with methotrexate (IC 50 ¼ 0.14 ± 1.25 mM). The in silico studies were done to calculate the drug-likeness and toxicity risk parameters of the newly synthesised derivatives. Additionally, the high potency of the pyrazole derivatives bearing sulphonamide against DHFR was confirmed with molecular docking and might be used as an optimum lead for further modification.

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“…1,2,3-Triazoles hold a significant importance in drug discovery for their ability to evoke a myriad of biological activities, chief among these being their antiprotozoal activities against the pathogens of diseases such as malaria, 20 leishmaniasis 21 and trypanosomiasis. 22 They are readily synthesized by Huisgen cycloaddition 23 or copper-catalyzed alkyne-azide cycloaddition (CuAAC) reactions 24 between terminal alkynes and azides.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and in vitro Leishmania promastigote growth inhibition efficacy of novel 4(3H)-quinazolinone derivatives

Ralph¹,

Zuma²,

Aucamp³

et al. 2020

Arkivoc

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Molecular hybridization is an increasingly important strategy in rational drug design and development. A series of novel quinazolinone-triazole hybrids have been synthesized and their antileishmanial activity investigated. Derivatives (E)-3-(prop-2-yn-1-yl)-2-styrylquinazolin-4(3H)-one, and (E)-3-{[1-(4-bromobenzyl)-1H-1,2,3-triazol-4-yl]methyl}-2-styrylquinazolin-4(3H)-one were observed to moderately inhibit the growth of promastigotes. An overall lack of significant antileishmanial activity may be attributable to the poor aqueous solubility of the derivatives. Future research endeavors will focus on potential remediation by investigating the anchoring of hydrophilic moieties to the quinazolinone scaffold.

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Convenient synthesis, antimalarial and antimicrobial potential of thioethereal 1,4-disubstituted 1,2,3-triazoles with ester functionality

Cited by 41 publications

References 34 publications

1,2,3-Triazole-containing hybrids as leads in medicinal chemistry: A recent overview

1,2,3-Triazole-containing hybrids as leads in medicinal chemistry: A recent overview

Novel heterocyclic hybrids of pyrazole targeting dihydrofolate reductase: design, biological evaluation and in silico studies

Synthesis and in vitro Leishmania promastigote growth inhibition efficacy of novel 4(3H)-quinazolinone derivatives

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