Synthesis, biological evaluation and molecular docking studies of chromone hydrazone derivatives as α -glucosidase inhibitors

Wang, Guangcheng; Chen, Ming; Wang, Jing; Peng, Yaping; Li, Luyao; Xie, Zhenzhen; Deng, Bing; Chen, Shan; Li, Wenbiao

doi:10.1016/j.bmcl.2017.05.007

Cited by 75 publications

(42 citation statements)

References 30 publications

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“…Step-1 Synthesis of 2-(3,4-Dichloro-benzoyl)-benzoic acid 2-(3,4-Dichloro-benzoyl)-benzoic acid was synthesized from respective pthelic anhydride dissolve in nitro benzene with heat and continuous stirring on magnetic stirrer then add Dichlorobenzene [ 50]. Close the heat and add Aluminum trichloride with continuous stirring till removal of HCL fumes.…”

Section: Methodsmentioning

confidence: 99%

Design and synthesis of anti-convulsant and anti-bacterial activity of new hydrazone derivatives

2020

Biointerface Res Appl Chem

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Synthesis of new hydrazone derivatives, starting from 2-(3, 4-Dichloro-benzoyl)-benzoic acid to 2-(3, 4-dichloro-benzoyl) - benzoic acid ethyl ester than converted into 2- (3, 4-Dichloro-benzoyl)-benzoic acid hydrazide with a substituted aldehyde. The structure of newly synthesized compounds was confirmed by analytical and spectral analysis IR, 1HNMR and MASS. For docking study, we took structures of ligand compounds (i.e. AK-series Compounds) and target protein structures into ‘pdb’ file format. Three compounds as possible anti-convulsant AK-1, AK-2 &Ak-4 were considered for compounds Ak-1 was not found suitable for anti-convulsant activity; while AK-2 & AK-4 have the capacity to show anti-convulsant activity with lesser affinity than controls. As an overall conclusion, except Ak-1, other compounds can be further used for anti- convulsant activity. Anti-convulsant activities were performed on rats by using maximal Electroshock Seizure test and minimal Neurotoxicity. Compound 2- (3, 4 – Dichloro-benzoyl)-benzoic acid (4- chloro-benzylidene) (AK-2) shows good anti-convulsant activity. The in-vitro antibacterial strains Escherichia coli MTCC 1573), and staphylococcus aureus (MTCC 1430), were used. Compound 2-(3, 4-Dichloro-benzoyl)-benzoic acid (2-notro-benzylidene-hydrazide (AK-1) gives the highest activity against Escherichia coli (MTCC 1573) and Staphylococcus aureus (MTCC-1430).

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Section: Methodsmentioning

confidence: 99%

Design and synthesis of anti-convulsant and anti-bacterial activity of new hydrazone derivatives

2020

Biointerface Res Appl Chem

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“…Diabetes is a group metabolic disorder characterized with high blood sugar levels over a long time. Frequent urination, increased thirst, and increased hunger are caused by high blood sugar, which if not addressed to, will result in serious health issues such as diabetic ketoacidosis, hyperosmolar hyperglycemic state, or death, cardiac and vascular diseases, thrombosis, stroke, chronic kidney disease, foot ulcers, and damage to the eyes ,,. Causes of diabetes are either the pancreas fail to produce enough insulin, or the cells of the body fail to respond adequately to the insulin produced.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of New Chiral (R)‐BINOL Derivatives under Microwave Irradiation and Evaluation of Their Antibacterial and α‐Glucosidase Inhibitory Activity

Ankireddy¹,

Paidikondala²,

Gundla³

et al. 2019

ChemistrySelect

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Series of new 3,3’‐disubstituted chiral (R)‐BINOL compounds have been synthesized with good yields and short reaction time under microwave‐irradiation. The titled compounds showed great antibacterial activity against gram‐positive and gram‐negative organisms. The results indicated that two compounds (R)‐3,3′‐bis(3,5‐difluorophenyl)‐[1,1′‐binaphthalene]‐2,2′‐diol (6 a) and (R)‐3,3′‐bis(4‐nitrophenyl)‐[1,1′‐binaphthalene]‐2,2′‐diol (6 d) which bearing fluoro and nitro substitution on phenyl group has displayed highest inhibition against pathogens. All the derivatives evaluated in vitro against α‐glucosidase. The results indicates that all the target compounds have significant inhibitory activity and more potent than standard drug Acarbose (IC50 = 586.391 ± 14.017 μM). (R)‐3,3′‐bis(3,5‐dichlorophenyl)‐[1,1′‐binaphthalene]‐2,2′‐diol (6 b), (R)‐3,3′‐bis(3,5‐difluorophenyl)‐[1,1′‐binaphthalene]‐2,2′‐diol (6 a), (R)‐3,3′‐bis(4‐nitrophenyl)‐[1,1′‐binaphthalene]‐2,2′‐diol (6 d) and (R)‐3,3′‐bis(3,5‐dimethylphenyl)‐[1,1′‐binaphthalene]‐2,2′‐diol (6 f) compounds shows strong inhibitors of α‐glucosidase, with the IC50 values of 25.341 ± 0.009 μM, 29.215 ± 0.017 μM, 30.294 ± 0.012 μM and 32.402 ± 0.041 μM, respectively.

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“…Substituted chromones represent one of the major classes of naturally occurring compounds . Chromones have shown diverse biological activities including antimicrobial , anti‐inflammatory , antioxidant , anticancer , antitumor , neuroprotective , and human immunodeficiency virus inhibitory .…”

Section: Introductionmentioning

confidence: 99%

Studies on the Chemical Reactions of Some 3‐Substituted‐6,8‐dimethylchromones with Nucleophilic Reagents

Ibrahim

Badran

El‐Gohary

et al. 2018

Journal of Heterocyclic Chem

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A variety of 3‐substituted‐6,8‐dimethylchromones have been synthesized and characterized. The chemical reactivity of 3‐substituted‐6,8‐dimethylchromones was studied towards some nucleophiles, namely, S‐benzyldithiocarbazate, o‐phenylenediamine, and cyanoacetamide, and a diversity of products were efficiently synthesized. Reactions of 3‐substituted‐6,8‐dimethylchromones (except 3‐formyl‐6,8‐dimethylchromone), with nucleophilic reagents, usually proceed through nucleophilic attack at C‐2 position followed by different types of heterocyclization depending on the functional group present at C‐3 position. Structures of the newly synthesized products have been established based on elemental analysis and spectral data.

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Synthesis, biological evaluation and molecular docking studies of chromone hydrazone derivatives as α -glucosidase inhibitors

Cited by 75 publications

References 30 publications

Design and synthesis of anti-convulsant and anti-bacterial activity of new hydrazone derivatives

Design and synthesis of anti-convulsant and anti-bacterial activity of new hydrazone derivatives

Synthesis of New Chiral (R)‐BINOL Derivatives under Microwave Irradiation and Evaluation of Their Antibacterial and α‐Glucosidase Inhibitory Activity

Studies on the Chemical Reactions of Some 3‐Substituted‐6,8‐dimethylchromones with Nucleophilic Reagents

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