Synthesis of 1H-1,2,3-triazole derivatives as new α-glucosidase inhibitors and their molecular docking studies

Avula, Satya Kumar; Khan, Ajmal; Rehman, Najeeb Ur; Anwar, Muhammad U.; Al-Abri, Zahra; Wadood, Abdul; Riaz, Muhammad; Csük, René; Al‐Harrasi, Ahmed

doi:10.1016/j.bioorg.2018.08.008

Cited by 86 publications

(46 citation statements)

References 44 publications

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“…13), exhibited activity against the target enzyme, which was the best among all the synthesised triazole derivatives, with IC 50 value of 14.2 µM in inhibition of the α-glucosidase enzyme. 133 Moreover, molecular modelling analysis revealed that 104 displayed a preferential binding mode by interacting with three active site residues Arg312, Glu304, and Phe158, which suggested that further developments of 104 may provide new lead compounds as antidiabetic drugs.…”

Section: Antidiabetic Activitymentioning

confidence: 99%

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: Antidiabetic Activitymentioning

confidence: 99%

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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“…[2][3][4][5][6][7] The structural framework of 1,2,3-triazole enables it to mimic different functional groups, justifying its wide use as a bioisostere for the synthesis of new active molecules possessing a broad range of biological activities that include antimicrobial, anticancer, and antiviral, along with antidiabetic, anti-inammatory, anti-Alzheimer, and antioxidant properties. 8,9 All these methodologies have permitted the successful design of novel drug analogs via combinatorial synthesis.…”

Section: Introductionmentioning

confidence: 99%

CuAAC-ensembled 1,2,3-triazole-linked isosteres as pharmacophores in drug discovery: review

et al. 2020

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“…Phen is a well-known enzyme inhibitor (McCann et al, 2012;Boumans et al, 1997;Sartorius et al, 1988) and copper-dca À complexes (Cui et al, 2011) were found to be urease active, whereas a tin-dca À complex (Saeed et al, 2010) showed some antibacterial and antifungal activity (vide supra). As an extension of our search for new potential -glucosidase and urease inhibitors (Avula et al, 2018;Ur Rehman et al, 2018;Arfan et al, 2010), we were interested in comparing the bioactivities of alkali/alkaline earth complexes of phen/dcaH. Complexes 1-3 were evaluated in in-vitro assays against urease and -glucosidase enzyme for inhibition studies using the literature-reported protocol (Choudhary et al, 2010;Arfan et al, 2010).…”

Section: Urease and A-glucosidase Enzyme Inhibitionmentioning

confidence: 99%

“…Notably, two mononuclear copper complexes (Cui et al, 2011) were found to be urease active, whereas a tetranuclear tin complex (Saeed et al, 2010) showed some antibacterial and antifungal activity. As a continuation of our search for new potential -glucosidase and urease inhibitors (Avula et al, 2018;Ur Rehman et al, 2018;Alam et al, 2019), we were interested in the bioactivities of alkali/alkaline earth complexes of phen/dcaH.…”

Section: Introductionmentioning

confidence: 99%

Crystal structure, shape analysis and bioactivity of new Li^I, Na^I and Mg^II complexes with 1,10-phenanthroline and 2-(3,4-dichlorophenyl)acetic acid

Shah

Ullah

et al. 2019

Acta Crystallogr C Struct Chem

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Reactions of 1,10-phenanthroline (phen) and 2-(3,4-dichlorophenyl)acetic acid (dcaH) with Mn (CO3) (M = LiI, NaI and MgII; n = 1 and 2) in MeOH yield the mononuclear lithium complex aqua[2-(3,4-dichlorophenyl)acetato-κO](1,10-phenanthroline-κ2 N,N′)lithium(I), [Li(C8H5Cl2O2)(C12H8N2)(H2O)] or [Li(dca)(phen)(H2O)] (1), the dinuclear sodium complex di-μ-aqua-bis{[2-(3,4-dichlorophenyl)acetato-κO](1,10-phenanthroline-κ2 N,N′)sodium(I)}, [Na2(C8H5Cl2O2)2(C12H8N2)2(H2O)2] or [Na2(dca)2(phen)2(H2O)2] (2), and the one-dimensional chain magnesium complex catena-poly[[[diaqua(1,10-phenanthroline-κ2 N,N′)magnesium]-μ-2-(3,4-dichlorophenyl)acetato-κ2 O:O′] 2-(3,4-dichlorophenyl)acetate monohydrate], {[Mg(C8H5Cl2O2)(C12H8N2)(H2O)2](C8H5Cl2O2)·H2O} n or {[Mg(dca)(phen)(H2O)2](dca)·H2O} n (3). In these complexes, phen binds via an N,N′-chelate pocket, while the deprotonated dca− ligands coordinate either in a monodentate (in 1 and 2) or bidentate (in 3) fashion. The remaining coordination sites around the metal ions are occupied by water molecules in all three complexes. Complex 1 crystallizes in the triclinic space group P\overline{1} with one molecule in the asymmetric unit. The Li+ ion adopts a four-coordinated distorted seesaw geometry comprising an [N2O2] donor set. Complex 2 crystallizes in the triclinic space group P\overline{1} with half a molecule in the asymmetric unit, in which the Na+ ion adopts a five-coordinated distorted spherical square-pyramidal geometry, with an [N2O3] donor set. Complex 3 crystallizes in the orthorhombic space group P212121, with one Mg2+ ion, one phen ligand, two dca− ligands and three water molecules in the asymmetric unit. Both dcaH ligands are deprotonated, however, one dca− anion is not coordinated, whereas the second dca− anion coordinates in a bidentate fashion bridging two Mg2+ ions, resulting in a one-dimensional chain structure for 3. The Mg2+ ion adopts a distorted octahedral geometry, with an [N2O4] donor set. Complexes 1–3 were evaluated against urease and α-glucosidase enzymes for their inhibition potential and were found to be inactive.

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Synthesis of 1H-1,2,3-triazole derivatives as new α-glucosidase inhibitors and their molecular docking studies

Cited by 86 publications

References 44 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

CuAAC-ensembled 1,2,3-triazole-linked isosteres as pharmacophores in drug discovery: review

Crystal structure, shape analysis and bioactivity of new Li^I, Na^I and Mg^II complexes with 1,10-phenanthroline and 2-(3,4-dichlorophenyl)acetic acid

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Synthesis of 1H-1,2,3-triazole derivatives as new α-glucosidase inhibitors and their molecular docking studies

Cited by 86 publications

References 44 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

CuAAC-ensembled 1,2,3-triazole-linked isosteres as pharmacophores in drug discovery: review

Crystal structure, shape analysis and bioactivity of new LiI, NaI and MgII complexes with 1,10-phenanthroline and 2-(3,4-dichlorophenyl)acetic acid

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Crystal structure, shape analysis and bioactivity of new Li^I, Na^I and Mg^II complexes with 1,10-phenanthroline and 2-(3,4-dichlorophenyl)acetic acid