2-(phenyl)-4H-chromen-4-ones: Green synthesis, characterization, in vitro antifungal evaluation and molecular docking approach toward Aspergillus fumigatus

Devi, Ahanthem Priyanca; Dhingra, Naveen; Bhardwaj, Uma; Chundawat, Rajendra Singh; Joshi, Chetan; Singh, Shivendra; Ameta, K. L.

doi:10.1016/j.crgsc.2021.100234

Cited by 4 publications

(4 citation statements)

References 20 publications

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“…Devi and co-workers 109 reported a 4-chromone-based compound 155 ( Scheme 32B ) as an antimicrobial agent. According to the authors, the synthesis of 155 involving microwave and ultrasonic irradiation should be considered a “green” one.…”

Section: Heterocyclic Inhibitors Targeting the Active Sites Of Glcn-6...mentioning

confidence: 99%

“…According to the authors, the synthesis of 155 involving microwave and ultrasonic irradiation should be considered a “green” one. The chalcone 154 , obtained from 2-hydroxyacetophenone and 2-chlorobenzaldehyde in the presence of Montmorillonite K under microwave irradiation, was cyclised to 4-chromone 155 in an alkaline environment of NaOH and the presence of tert -butyl hydroperoxide under ultrasonic irradiation ( Scheme 32B ) 109 . In a disc diffusion test, derivative 155 exhibited antifungal activity, comparable to that of the standard drug, fluconazole.…”

Section: Heterocyclic Inhibitors Targeting the Active Sites Of Glcn-6...mentioning

confidence: 99%

“…In a disc diffusion test, derivative 155 exhibited antifungal activity, comparable to that of the standard drug, fluconazole. Molecular docking studies on GlcN-6-P synthase (podbid: 2vf5) showed that 155 interacted with the ISOM domain active site (docking score −89.68) via hydrogen bond formation with Glu384, Ser349 and Lys603 residues 109 .…”

Section: Heterocyclic Inhibitors Targeting the Active Sites Of Glcn-6...mentioning

confidence: 99%

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Inhibitors of glucosamine-6-phosphate synthase as potential antimicrobials or antidiabetics – synthesis and properties

Stefaniak

Nowak

Wojciechowski

et al. 2022

Journal of Enzyme Inhibition and Medicinal Chemistry

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Glucosamine-6-phosphate synthase (GlcN-6-P synthase) is known as a promising target for antimicrobial agents and antidiabetics. Several compounds of natural or synthetic origin have been identified as inhibitors of this enzyme. This set comprises highly selective l -glutamine, amino sugar phosphate or transition state intermediate cis -enolamine analogues. Relatively low antimicrobial activity of these inhibitors, poorly penetrating microbial cell membranes, has been improved using the pro-drug approach. On the other hand, a number of heterocyclic and polycyclic compounds demonstrating antimicrobial activity have been presented as putative inhibitors of the enzyme, based on the results of molecular docking to GlcN-6-P synthase matrix. The most active compounds of this group could be considered promising leads for development of novel antimicrobial drugs or antidiabetics, provided their selective toxicity is confirmed.

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Section: Heterocyclic Inhibitors Targeting the Active Sites Of Glcn-6...mentioning

confidence: 99%

Section: Heterocyclic Inhibitors Targeting the Active Sites Of Glcn-6...mentioning

confidence: 99%

Section: Heterocyclic Inhibitors Targeting the Active Sites Of Glcn-6...mentioning

confidence: 99%

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Inhibitors of glucosamine-6-phosphate synthase as potential antimicrobials or antidiabetics – synthesis and properties

Stefaniak

Nowak

Wojciechowski

et al. 2022

Journal of Enzyme Inhibition and Medicinal Chemistry

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“…It has been reported that chromone and its derivatives have a wide range of pharmacological activities such as antioxidant (Shatokhin et al, 2022), antitumor (Sun et al, 2022), antiviral (Fu et al, 2020), fungicidal (Devi et al, 2022), insecticidal (Hussein et al, 2018), antibacterial (Reddy et al, 2018), and anti‐inflammatory activities (Chu et al, 2021; Reddy et al, 2018). Recent studies have shown that many natural and synthetic derivatives containing chromone nucleus can be used as α‐glucosidase inhibitors (Mi et al, 2021).…”

Section: Introductionmentioning

confidence: 99%

Synthesis, biological evaluation, and molecular docking study of chromen‐linked hydrazine carbothioamides as potent α‐glucosidase inhibitors

Basri

Ullah

Halim

et al. 2023

Drug Development Research

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Inhibiting α‐glucosidase is a reliable method for reducing blood sugar levels in diabetic individuals. Several novel chromen‐linked hydrazine carbothioamide (3a–r) were designed and synthesized by condensation of chromone‐3‐carbaldehyde with a variety of substituted thiosemicarbazides. The structures of these new analogues were elucidated through various advanced spectroscopic techniques (1H NMR, 13C NMR, and ESI‐MS). The resulted compounds were screened for α‐glucosidase inhibitory potential and all the compounds (3a–r) exhibited potent inhibition of α‐glucosidase with IC50 values ranging 0.29–53.70 µM. Among them compounds 3c, 3f, 3h, and 3r displayed the highest α‐glucosidase inhibitor capability with IC50 values of 1.50, 1.28, 1.08, and 0.29 µM, respectively. Structure–activity relationship showed that different substituted groups are responsible for the variation in the α‐glucosidase inhibition. The kinetics studies of the most active inhibitor (3r) were performed, to investigate the mode of inhibition and dissociation constants (Ki), that indicated a competitive inhibitor with Ki value of 1.47 ± 0.31 µM. Furthermore, molecular docking studies was performed to reveal the possible interactions, such as H‐bonding, or π–π stacking, with the key residues of α‐glucosidase. Docking analysis revealed the importance of hydrazine carbothioamide moiety of compounds in the attachment of ligands with the crucial residues of α‐glucosidase. The estimated pharmacokinetic, physicochemical, and drug likeness properties of compounds 3a–r reflects that these molecules have acceptable range of these properties.

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Mesoporous ZnCr ₂ O ₄ Nanocatalyst with High Specific Surface Area for Facile Synthesis of Flavonoid Derivatives

Amiri

Nazarpour

Mohave

et al. 2023

Polycyclic Aromatic Compounds

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2-(phenyl)-4H-chromen-4-ones: Green synthesis, characterization, in vitro antifungal evaluation and molecular docking approach toward Aspergillus fumigatus

Cited by 4 publications

References 20 publications

Inhibitors of glucosamine-6-phosphate synthase as potential antimicrobials or antidiabetics – synthesis and properties

Inhibitors of glucosamine-6-phosphate synthase as potential antimicrobials or antidiabetics – synthesis and properties

Synthesis, biological evaluation, and molecular docking study of chromen‐linked hydrazine carbothioamides as potent α‐glucosidase inhibitors

Mesoporous ZnCr ₂ O ₄ Nanocatalyst with High Specific Surface Area for Facile Synthesis of Flavonoid Derivatives

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2-(phenyl)-4H-chromen-4-ones: Green synthesis, characterization, in vitro antifungal evaluation and molecular docking approach toward Aspergillus fumigatus

Cited by 4 publications

References 20 publications

Inhibitors of glucosamine-6-phosphate synthase as potential antimicrobials or antidiabetics – synthesis and properties

Inhibitors of glucosamine-6-phosphate synthase as potential antimicrobials or antidiabetics – synthesis and properties

Synthesis, biological evaluation, and molecular docking study of chromen‐linked hydrazine carbothioamides as potent α‐glucosidase inhibitors

Mesoporous ZnCr 2 O 4 Nanocatalyst with High Specific Surface Area for Facile Synthesis of Flavonoid Derivatives

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Product

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About

Mesoporous ZnCr ₂ O ₄ Nanocatalyst with High Specific Surface Area for Facile Synthesis of Flavonoid Derivatives