New quinoline-based triazole hybrid analogs as effective inhibitors of α-amylase and α-glucosidase: Preparation, in vitro evaluation, and molecular docking along with in silico studies

Khan, Yousaf; Iqbal, Shahid; Shah, Mazloom; Maalik, Aneela; Hussain, Rafaqat; Khan, Shoaib; Khan, Imran; Pashameah, Rami Adel; Alzahrani, Eman; Farouk, Abd‐ElAziem; Alahmdi, Mohammed Issa; Abd-Rabboh, Hisham S.M.

doi:10.3389/fchem.2022.995820

Cited by 27 publications

(3 citation statements)

References 32 publications

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“…Moreover, ILs allow for covalent and non-covalent modifications of multiwall carbon nanotubes (MWCNT) without damaging the π-conjugated nanotube structure. The non-covalent interactions between imidazolium ILs and hexagonally arranged sp 2 -hybridized aromatic carbon atoms are mostly based on van der Waals forces and π-electronic interactions, which are also found in similar systems [25,26].…”

Section: Resultsmentioning

confidence: 87%

Green Dynamic Kinetic Resolution—Stereoselective Acylation of Secondary Alcohols by Enzyme-Assisted Ruthenium Complexes

Heba

Wolny

Kastelik-Hryniewiecka

et al. 2022

Catalysts

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Dynamic kinetic resolution allows for the synthesis of enantiomerically pure asymmetric alcohols. Cyclopentadienyl-derived ruthenium catalysts were immobilized with an ionic liquid, [BMIM][NTf2], on multiwall carbon nanotubes and used for the racemization of chiral secondary alcohols. This successful approach was combined with the enantioselective enzymatic acylation of secondary alcohols (1-phenylethanol and 1-(1-naphthyl)ethanol) using Novozyme® 435. The resulting catalytic system of the ruthenium racemization catalysts and enzymatic acylation led to chiral esters being obtained by dynamic kinetic resolution. The immobilized catalytic system in the ionic liquid gave the same activity of >96% yield within 6 h and a selectivity of 99% enantiomeric excess as the homogeneous system, while allowing for the convenient separation of the desired products from the catalyst. Additionally, the process can be regarded as green, since the efficient reuse of the catalytic system was demonstrated.

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Section: Resultsmentioning

confidence: 87%

Green Dynamic Kinetic Resolution—Stereoselective Acylation of Secondary Alcohols by Enzyme-Assisted Ruthenium Complexes

Heba

Wolny

Kastelik-Hryniewiecka

et al. 2022

Catalysts

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“…In case of analog 5 and 6, interactions were found such as vander Waals, conventional hydrogen bond, Pi-anion, Pi-Sigma, alkyl, Pi-alkyl, salt bridge, halogen, Pi-sulphur, etc. The further detail of docking study were summarized as in our previous articles [ 30 , 31 , 32 , 33 , 34 , 35 ] and the assay protocols of both the activities have been added in Supplementary file [ 36 , 37 ].…”

Section: Biological Profilementioning

confidence: 99%

Synthesis, In Vitro Anti-Microbial Analysis and Molecular Docking Study of Aliphatic Hydrazide-Based Benzene Sulphonamide Derivatives as Potent Inhibitors of α-Glucosidase and Urease

et al. 2022

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A unique series of sulphonamide derivatives was attempted to be synthesized in this study using a new and effective method. All of the synthesized compounds were verified using several spectroscopic methods, including FTIR, 1H-NMR, 13C-NMR, and HREI-MS, and their binding interactions were studied using molecular docking. The enzymes urease and α-glucosidase were evaluated against each derivative (1–15). When compared to their respective standard drug such as acarbose and thiourea, almost all compounds were shown to have excellent activity. Among the screened series, analogs 5 (IC50 = 3.20 ± 0.40 and 2.10 ± 0.10 µM) and 6 (IC50 = 2.50 ± 0.40 and 5.30 ± 0.20 µM), emerged as potent molecules when compared to the standard drugs acarbose (IC50 = 8.24 ± 0.08 µM) and urease (IC50 = 7.80 ± 0.30). Moreover, an anti-microbial study also demonstrated that analogs 5 and 6 were found with minimum inhibitory concentrations (MICs) in the presence of standard drugs streptomycin and terinafine.

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“…Molecular hybridization is a new concept in drug design and development based on the combination of two or more than two bioactive moieties to produce a new hybrid compound with improved biological activities, when compared to the parent drugs. In the past, researchers had synthesized bishydrazone 37,38 and triazole analogues 36,39 as α-glucosidase and α-amylase inhibitors individually, but no one had incorporated both these bioactive entities in the same molecules to enhance the biological potentials. Therefore, this research work was carried out to incorporate both triazole and bis-hydrazone entities in the same compounds to further enhance the αamylase and α-glucosidase activities as the more the heteroatoms in the bulk structure of the compound, the more will be its chance of interactions with the active sites of the targeted enzymes, which in turn enhances the biological profile.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and In Vitro α-Amylase and α-Glucosidase Dual Inhibitory Activities of 1,2,4-Triazole-Bearingbis-Hydrazone Derivatives and Their Molecular Docking Study

et al. 2023

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There is an increasing prevalence of diabetes mellitus throughout the world, and new compounds are necessary to combat this. The currently available antidiabetic therapies are long-term complicated and side effect-prone, and this has led to a demand for more affordable and more effective methods of tackling diabetes. Research is focused on finding alternative medicinal remedies with significant antidiabetic efficacy as well as low adverse effects. In this research work, we have focused our efforts to synthesize a series of 1,2,4-triazole-based bis-hydrazones and evaluated their antidiabetic properties. In addition, the precise structures of the synthesized derivatives were confirmed with the help of various spectroscopic techniques including 1H-NMR, 13C-NMR, and HREI-MS. To find the antidiabetic potentials of the synthesized compounds, in vitro α-glucosidase and α-amylase inhibitory activities were characterized using acarbose as the reference standard. From structure–activity (SAR) analysis, it was confirmed that any variation found in inhibitory activities of both α-amylase and α-glucosidase enzymes was due to the different substitution patterns of the substituent(s) at variable positions of both aryl rings A and B. The results of the antidiabetic assay were very encouraging and showed moderate to good inhibitory potentials with IC50 values ranging from 0.70 ± 0.05 to 35.70 ± 0.80 μM (α-amylase) and 1.10 ± 0.05 to 30.40 ± 0.70 μM (α-glucosidase). The obtained results were compared to those of the standard acarbose drug (IC50 = 10.30 ± 0.20 μM for α-amylase and IC50 = 9.80 ± 0.20 μM for α-glucosidase). Specifically, compounds 17, 15, and 16 were found to be significantly active with IC50 values of 0.70 ± 0.05, 1.80 ± 0.10, and 2.10 ± 0.10 μM against α-amylase and 1.10 ± 0.05, 1.50 ± 0.05, and 1.70 ± 0.10 μM against α-glucosidase, respectively. These findings reveal that triazole-containing bis-hydrazones act as α-amylase and α-glucosidase inhibitors, which help develop novel therapeutics for treating type-II diabetes mellitus and can act as lead molecules in drug discovery as potential antidiabetic agents.

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New quinoline-based triazole hybrid analogs as effective inhibitors of α-amylase and α-glucosidase: Preparation, in vitro evaluation, and molecular docking along with in silico studies

Cited by 27 publications

References 32 publications

Green Dynamic Kinetic Resolution—Stereoselective Acylation of Secondary Alcohols by Enzyme-Assisted Ruthenium Complexes

Green Dynamic Kinetic Resolution—Stereoselective Acylation of Secondary Alcohols by Enzyme-Assisted Ruthenium Complexes

Synthesis, In Vitro Anti-Microbial Analysis and Molecular Docking Study of Aliphatic Hydrazide-Based Benzene Sulphonamide Derivatives as Potent Inhibitors of α-Glucosidase and Urease

Synthesis and In Vitro α-Amylase and α-Glucosidase Dual Inhibitory Activities of 1,2,4-Triazole-Bearingbis-Hydrazone Derivatives and Their Molecular Docking Study

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