Synthesis, Theoretical Calculation and α-glucosidase inhibition of new chalcone oximes

Fandaklı, Seda; Doğan, İnci Selin; Sellitepe, Hasan Erdinç; Yaşar, Ahmet; Yaylı, Nurettin

doi:10.25135/acg.oc.38.18.02.067

Cited by 6 publications

(5 citation statements)

References 23 publications

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“…semicarbazone and thiosemicarbazone 3-phenylquinazoline-2,4(1H,3H)-dione active Schiff bases (Muleta & Desalegn, 2022;Soman & Jain, 2022), ferrocene Chalcone-based Schiff bases (Liu et al, 2018), 1,2,4-oxadiazole-chalcone/ oxime hybrids Schiff base hybrids (Ibrahim et al, 2021), hydrazinecarbothiamide and hydrazine-carboxamide Schiff base derivatives (Siddiqui et al, 2019) and deoxybenzoin Chalconebased Schiff base hybrids (Luo et al, 2012) with anticancer (Liu et al, 2018), antimicrobial (Aiwonegbe & Usifoh, 2021), antioxidant (Muleta & Desalegn, 2022), antidiabetic (Fandaklı et al, 2018), immunosuppressant (Luo et al, 2012) and tyrosine inhibitors (Radhakrishnan et al, 2016), were reported.…”

Section: Graph Theoretical Analysis Pharmacoinformatics and Molecular...mentioning

confidence: 99%

Graph theoretical analysis, pharmacoinformatics and molecular docking investigation of Chalcone-Schiff base hybrids as Cyclin-Dependent kinase inhibitors

Sekar,

Arivanantham,

Jaishankar

et al. 2024

RIP

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One of the promising classes of compounds in medicinal chemistry and drug design is those with azomethine linkages. The Chalcone-Schiff base hybrids contain this linkage and some heteroatoms, which are versatile molecules, play a vital role in drug discovery and development with enormous therapeutic applications. In this view, the present work deals with the investigation of the in silico biological potential of the Chalcone-Schiff base hybrids based on the network pharmacology approach. From the results obtained from network pharmacology, the Cyclin-dependent kinase (CDK) isoforms were identified as the potential targets and the CDK inhibitory activity of the compounds was investigated using molecular docking studies. The in silico pharmacokinetic, metabolic and theoretical studies at DFT level were performed. Molecular docking studies revealed that the compounds have better CDK inhibitory potential with better binding affinity and interaction profile. Among the tested compounds, (Z)-2-((4,6-diphenyl-5,6-dihydro-4H-1,3-thiazin-2-yl)imino)-2,3-dihydro-1H-inden-1-one was found to be the most active compound than the standards, palbociclib and dinaciclib against the CDK isoforms (CDK1, CDK2 and CDK4) with the binding energies of -9.9, -10.3 and -10 Kcal/Mol, respectively. Also, this compound exhibited better pharmacokinetic and metabolic properties along with better solubility. The theoretical studies at the DFT level also indicate that the compound has better metabolic stability and the electron transfer from HOMO to LUMO was observed. Thus, the tested Chalcone-Schiff base hybrids can be used effectively for the inhibition of CDK isoforms.

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Section: Graph Theoretical Analysis Pharmacoinformatics and Molecular...mentioning

confidence: 99%

Graph theoretical analysis, pharmacoinformatics and molecular docking investigation of Chalcone-Schiff base hybrids as Cyclin-Dependent kinase inhibitors

Sekar,

Arivanantham,

Jaishankar

et al. 2024

RIP

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“…The antidiabetic activity of the synthesized ligands was determined by the α-Glucosidase inhibition assay against acarbose. Both of the compounds showed significant activity 10 and the structures of these compounds are given in figure 5. the status of the caspase 3 protein by using anti-cleaved caspase 3 antibodies.…”

Section: Chalcone-based Schiff Base Derivatives As Antidiabetic Agentsmentioning

confidence: 99%

“…The chalcones are also of great importance due to their various therapeutic applications and diverse applications. The Schiff bases based on chalcone derivatives such as pyrazole and 2-pyrazoline derivatives 7 , thiosemicarbazone derivatives and other derivatives exhibited various pharmacological activities like antimicrobial 8 , anticancer 9 , antidiabetic 10 and antioxidant activities 11 . These Schiff base linkages (azo or imine) enhance the sensing properties of the thermotropic liquid crystals, provides thermal stability and also the liquid crystalline properties of the compounds containing chalcone linkages are enhanced 12 .…”

Section: Introductionmentioning

confidence: 99%

A Review on Chemistry, Synthesis and Biological Applications of Chalcone-based Schiff Bases

Sekar

Kumar

Raju

2023

J. Drug Delivery Ther.

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Heterocyclic compounds are an important class of compounds in the field of pharmaceutical and synthetic organic chemistry. The Schiff bases contain azomethine linkages which are obtained by the condensation of aldehyde/ketone with amines. Among the various types of Schiff bases, the chalcone-based Schiff bases play a vital role in the treatment of various ailments and various applications, which can be synthesized by using different types of chalcones as the starting materials. These types of compounds were synthesized by using various techniques like conventional means of synthesis, microwave-assisted reaction, heterocyclic catalyst-mediated synthesis and also by means of trituration. The chalcone or bis-chalcone-based Schiff bases and their derivatives contain -C=N linkage which exhibits various activities including antimicrobial, anticancer, antioxidant, antidiabetic and immunosuppressant activities. Beyond these activities, these types of Schiff bases are also used in various chemical industries and fluorescent sensors, which also play a major role in the field of synthetic organic chemistry and coordination chemistry as intermediates. This review discusses the numerous synthetic strategies along with their applications in the field of medicine. Thus, this review will be helpful in developing more effective drug-like scaffolds for use in future drug design. Keywords: Schiff bases, Chalcone-based Schiff bases, Antimicrobial, Anticancer, Antioxidant, Biological Applications

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“…Fandaklı et al (2018) reported the α-glucosidase inhibitory activity of synthesized chalcone oximes (2a-2k). Amongst tested compounds, compounds 2a and 2b showed more effective activity against α-glucosidase with IC 50 values of 1.61 ± 0.16 µM and 3.36 ± 0.58 µM [ 26 ].…”

Section: Reviewmentioning

confidence: 99%

A Review of the In Vitro Inhibition of α-Amylase and α-Glucosidase by Chalcone Derivatives

Tran¹,

Tu²,

Hoang³

et al. 2023

Cureus

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Diabetes mellitus is a chronic metabolic disease relating to steady hyperglycemia resulting from the impairment of the endocrine and non-endocrine systems. Many new drugs having varied targets were discovered to treat this disease, especially type 2 diabetes. Among those, α-glucosidase inhibitors showed their effects by preventing the digestion of carbohydrates through their inhibition against α-amylase and αglucosidase. Recently, chalcones have attracted considerable attention as they have a simple structure, are easily synthesized as well as have a variety of derivatives. Some reports suggested that chalcone and its derivates could inhibit α-amylase and α-glucosidase. This narrative review provides a comprehensive evaluation of the inhibition of chalcone and its derivatives against α-amylase and α-glucosidase that were reviewed and reported in published scientific articles. Twenty-eight articles were reviewed after screening 207 articles found in four databases, including PubMed, Google Scholar, VHL (Virtual Health Library), and GHL (Global Health Library). This review presented the inhibitory effects of varied chalcones, including chalcones with a basic structural framework, azachalcones, bis-chalcones, chalcone oximes, coumarinchalcones, cyclohexane chalcones, dihydrochalcones, and flavanone-coupled chalcones. Many of these chalcones had significant inhibition against α-amylase as well as α-glucosidase that were comparable to or even stronger than standard inhibitors. This suggested that such compounds could be potential candidates for the discovery of new anti-diabetic remedies in the years to come.

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Synthesis, Theoretical Calculation and α-glucosidase inhibition of new chalcone oximes

Cited by 6 publications

References 23 publications

Graph theoretical analysis, pharmacoinformatics and molecular docking investigation of Chalcone-Schiff base hybrids as Cyclin-Dependent kinase inhibitors

Graph theoretical analysis, pharmacoinformatics and molecular docking investigation of Chalcone-Schiff base hybrids as Cyclin-Dependent kinase inhibitors

A Review on Chemistry, Synthesis and Biological Applications of Chalcone-based Schiff Bases

A Review of the In Vitro Inhibition of α-Amylase and α-Glucosidase by Chalcone Derivatives

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