Design, synthesis, docking and biological evaluation of chalcones as promising antidiabetic agents

Rammohan, Aluru; Bhaskar, Baki Vijaya; Venkateswarlu, N. B.; Gu, Wei; Zyryanov, Grigory V.

doi:10.1016/j.bioorg.2019.103527

Cited by 48 publications

(27 citation statements)

References 28 publications

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“…The presence of saturated CH2 group of indanone counterpart in both synthesized compounds is confirmed by the peaks at 4.01-4.05 and 4.05 ppm in the 1 H NMR spectra of TFMBD-1 and TFMBD-2, respectively. The same CH2 group can be confirmed in both TFMBD-1 and TFMBD-2 by finding peaks at 32.27 and 32.30 ppm in 13 C NMR spectra. In 1 H NMR, the aromatic protons in both compounds were found in the range of 7.31 to 7.93 ppm.…”

Section: Antimicrobial Screeningsupporting

confidence: 54%

“…The chemicals (Make-Sigma Aldrich and SD Fine) were procured and utilized as received from Virion Enterprises Mumbai and Sigma Laboratory Nashik. A powerful multinuclear FT-NMR Spectrometer (500 MHz) model Advance-II was used for the 1 H NMR and 13 C investigations (Bruker). Chemical shifts in ppm relative to TMS were measured after the tilted compounds were dissolved in CDCl3.…”

Section: General Remarksmentioning

confidence: 99%

“…The physical and spectral study of the title compounds agrees well with previous published data. The 1 H NMR and 13 C NMR spectroscopic methods were used to characterize the synthesized compounds. The 1 H NMR analysis of the two compounds revealed a strong link between their structures.…”

Section: Antimicrobial Screeningmentioning

confidence: 99%

“…Chalcones and their derivatives are high captivating organic compounds due to their wide range of pharmacological applications. In the biosynthesis of flavonoids and isoflavonoids, chalcones are the vitally important intermediates [1][2][3][4][5] and display various biological functions such as anticancer, [6] antibacterial, [7] antituberculosis, [8] antiinflammatory, [9] antimalarial, [10] antiviral, [11] antifungal, [12] antidiabetic, [13] antioxidant, [14] activities. Chalcones are an enticing building block for integrating a conjugated motif into possible drugs or monomers.…”

Section: Introductionmentioning

confidence: 99%

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Antimicrobial and computational investigation of two 2,3‐dihydro‐1H‐inden‐1‐one derived fluorinated chalcone motifs

Shinde,

Adole,

Jagdale

2021

Vietnam Journal of Chemistry

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In this work, we report the anti‐microbial and computational study of two 2,3‐dihydro‐1H‐inden‐1‐one derived fluorinated chalcone scaffolds. The (E)‐2‐(4‐(trifluoromethyl)benzylidene)‐2,3‐dihydro‐1H‐inden‐1‐one (TFMBD‐1) and (E)‐2‐(4‐(trifluoromethoxy)benzylidene)‐2,3‐dihydro‐1H‐inden‐1‐one (TFMBD‐2) were synthesized by Claisen‐Schmidt reaction. The in‐depth structural analysis of optimized molecular structures, bond lengths and bond angles has been discussed by using density functional theory (DFT) with B3LYP/6‐311++G(d,p) basis set. The geometrical parameters, frontier molecular orbitals, global reactivity parameters, and MESP surfaces were all predicted using the same basis set on completely optimized geometries. Ionization potential, electron affinity, electronegativity, chemical hardness, global softness, global electrophilicity, and chemical potential were calculated using HOMO and LUMO energy values. Besides, the synthesized compounds were screened for their in‐vitro antibacterial and antifungal study. Antibacterial activity was screened against two Gram‐negative bacteria, E. coli and P. vulgaris, as well as against two Gram‐positive bacteria, S. aureus and B. subtilis, and antifungal activity was evaluated against A. niger and C. albicans. The TFMBD‐1 was revealed to be a more effective antibacterial and antifungal agent than TFMBD‐2.

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Section: Antimicrobial Screeningsupporting

confidence: 54%

Section: General Remarksmentioning

confidence: 99%

Section: Antimicrobial Screeningmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Antimicrobial and computational investigation of two 2,3‐dihydro‐1H‐inden‐1‐one derived fluorinated chalcone motifs

Shinde,

Adole,

Jagdale

2021

Vietnam Journal of Chemistry

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“…Among these classes of α,β-unsaturated carbonyl compounds, only the 4-aminochalcones and their N -tosyl derivatives were found to exhibit significant and increased inhibitory activities against these carbohydrate hydrolyzing enzymes, respectively. An in vivo study carried out with alloxan induced diabetic Wister male albino rats (100 mg/kg) revealed the 4-aminochalcones to exhibit significant antidiabetic efficacy with decreased blood glucose levels in the diabetic rats compared with control rats [ 23 ]. Molecular docking (in silico) study of the 4-aminochalcones into α-glucosidase binding sites revealed π–π stacked, π-cationic, polar, electrostatic and hydrophobic bonding interactions with key residues in the binding pockets of this enzyme [ 24 ].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Structure, Carbohydrate Enzyme Inhibition, Antioxidant Activity, In Silico Drug-Receptor Interactions and Drug-Like Profiling of the 5-Styryl-2-Aminochalcone Hybrids

2021

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The 2-amino-5-(3/4-fluorostyryl)acetophenones were prepared and reacted with benzaldehyde derivatives to afford the corresponding 5-styryl-2-aminochalcone hybrids. The trans geometry of the styryl and α,β-unsaturated carbonyl arms, and the presence of NH…O intramolecular hydrogen bond were validated using 1H-NMR and X-ray data. The 2-amino-5-styrylacetophenones and their 5-styryl-2-aminochalcone derivatives were screened in vitro for their capability to inhibit α-glucosidase and/or α-amylase activities. Their antioxidant properties were evaluated in vitro through the 2,2-diphenyl-1-picrylhydrazyl (DPPH) and nitric oxide (NO) free radical scavenging assays. Kinetic studies of the most active derivatives from each series against α-glucosidase and/or α-amylase activities have been performed supported by molecular docking studies to determine plausible protein–ligand interactions on a molecular level. The key aspects of the pharmacokinetics of these compounds, i.e., absorption, distribution, metabolism, and excretion have also been simulated at theoretical level. The most active compounds from each series, namely, 2a and 3e, were evaluated for cytotoxicity against the normal monkey kidney cells (Vero cells) and the adenocarcinomic human epithelial (A549) cell line to establish their safety profile at least in vitro.

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Naphthyl‐Based Chalcone Derivatives: A Multifaceted Player in Medicinal Chemistry

Mahesha,

Shetty

2024

ChemistrySelect

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Research has placed a great deal of emphasis on molecule development and discovery with substantial biological profiling in recent years. Despite the significant side effects, medicinal chemists have long strived to synthesize drug molecules with the highest level of therapeutic activity and the lowest possible level of toxicity. The naphthyl‐based chalcone derivatives have drawn attention due to their simple structures and wide range of pharmacological effects. The main focus of this review is to outline the biologically active molecules based on naphthyl moiety‐substituted chalcone derivatives developed over the years. A synopsis of pharmacological screening, including relevant structure‐activity relationships, action mechanisms, and possible therapeutic applications, is provided in this article. It is true that prospective hybrids combining the naphthyl moiety with different chalcone pharmacophores are needed to address drug resistance and improve specificity. Therefore, this review may be useful in the development and design of new, highly successful therapeutic drugs based on previously reported methodologies.

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Design, synthesis, docking and biological evaluation of chalcones as promising antidiabetic agents

Cited by 48 publications

References 28 publications

Antimicrobial and computational investigation of two 2,3‐dihydro‐1H‐inden‐1‐one derived fluorinated chalcone motifs

Antimicrobial and computational investigation of two 2,3‐dihydro‐1H‐inden‐1‐one derived fluorinated chalcone motifs

Synthesis, Structure, Carbohydrate Enzyme Inhibition, Antioxidant Activity, In Silico Drug-Receptor Interactions and Drug-Like Profiling of the 5-Styryl-2-Aminochalcone Hybrids

Naphthyl‐Based Chalcone Derivatives: A Multifaceted Player in Medicinal Chemistry

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