Design, synthesis, in-vitro and in-silico studies of chromone‐isoxazoline conjugates as anti‐bacterial agents

Kanzouai, Youssra; Chalkha, Mohammed; Hadni, Hanine; Laghmari, Mustapha; Bouzammit, Rachid; Nakkabi, Asmae; Benali, Taoufiq; Tüzün, Burak; Akhazzane, Mohamed; Yazidi, Mohamed El; Houari, Ghali Al

doi:10.1016/j.molstruc.2023.136205

Cited by 15 publications

(3 citation statements)

References 65 publications

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“…Also, its 1 H-NMR spectrum displayed multiplets belonging to 10 aromatic protons of carbazole and chromone rings in the range of d 7.09-8.14 ppm, while the allylic protons were resonated at d 4.55 (d, J = 4.8 Hz, CH 2 ), 5.27 (dd, J = 6.4 and 1.2 Hz, ]CH 2 ), and 5.97-6.06 (m, ] CH). 44,45 The signals of the methyl and ethyl groups appeared at…”

Section: Synthesis and Characterizationmentioning

confidence: 99%

Novel carbazolyl–thiazolyl–chromone and carbazolyl–thiazolyl–pyrazole hybrids: synthesis, cytotoxicity evaluation and molecular docking studies

Hassanin,

Ali,

Assiri

et al. 2024

RSC Adv.

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Section: Synthesis and Characterizationmentioning

confidence: 99%

Novel carbazolyl–thiazolyl–chromone and carbazolyl–thiazolyl–pyrazole hybrids: synthesis, cytotoxicity evaluation and molecular docking studies

Hassanin,

Ali,

Assiri

et al. 2024

RSC Adv.

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“…Given the biological significance of heterocycles, and in continuation of our research efforts focused on the synthesis and development of new bioactive heterocycles [ 40 , 41 , 42 ], the study undertaken in the present work aims at the synthesis and structural identification of a novel range of heterocyclic molecules possessing a triazole and isoxazole as the basic structure, derived from 3-formylchromone using N-alkylation and 1,3-DC reactions. Furthermore, the synthesized heterocyclic compounds have been evaluated for their antibacterial activities through both in vitro and in silico studies.…”

Section: Introductionmentioning

confidence: 99%

New Triazole-Isoxazole Hybrids as Antibacterial Agents: Design, Synthesis, Characterization, In Vitro, and In Silico Studies

Bouzammit,

Belchkar,

El fadili

et al. 2024

Molecules

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Novel isoxazole–triazole conjugates have been efficiently synthesized using 3-formylchromone as starting material according to a multi-step synthetic approach. The structures of the target conjugates and intermediate products were characterized by standard spectroscopic techniques (1H NMR and 13C NMR) and confirmed by mass spectrometry (MS). The all-synthesized compounds were screened for their antibacterial activity against three ATCC reference strains, namely Staphylococcus aureus ATCC 25923, Staphylococcus aureus ATCC BAA-44, and Escherichia coli ATCC 25922 as well as one strain isolated from the hospital environment Pseudomonas aeruginosa. The findings indicate that conjugate 7b exhibits a stronger antibacterial response against the tested Escherichia coli ATCC 25922 and Pseudomonas aeruginosa pathogenic strains compared to the standard antibiotics. Furthermore, hybrid compound 7b proved to have a bactericidal action on the Escherichia coli ATCC 25922 strain, as evidenced by the results of the MBC determination. Moreover, the ADMET pharmacokinetic characteristics revealed a favorable profile for the examined compound, as well as a good level of oral bioavailability. Molecular docking and molecular dynamics simulations were performed to explore the inhibition mechanism and binding energies of conjugate 7b with the proteins of Escherichia coli and Pseudomonas aeruginosa bacterial strains. The in silico results corroborated the data observed in the in vitro evaluation for compound 7b.

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“…[19][20][21][22][23] Chromone, known as a class of natural drugs, characterized by a benzoannelated γ-pyrone ring, exhibited the potential to behave as a privileged scaffold for the development of novel molecules in the development of new drugs. These chromone analogs have been found to exhibit a broad spectrum of pharmacological activities, encompassing antibacterial, [24] antioxidant, [25] anticancer, [26] antiinflammatory, [27] and antileishmanial properties. [28] Additionally, both natural and synthetic chromone derivatives have demonstrated noteworthy inhibitory activities against α-glucosidase, suggesting their relevance in addressing diabetes-related concerns.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of the chromone‐thiosemicarbazone scaffold as promising α‐glucosidase inhibitors: An in vitro and in silico approach toward antidiabetic drug design

Alharthy,

Khalid,

Fatima

et al. 2024

Archiv der Pharmazie

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Diabetes is a serious metabolic disorder affecting individuals of all age groups and prevails globally due to the failure of previous treatments. This study aims to address the most prevalent form of type 2 diabetes mellitus (T2DM) by reporting on the design, synthesis, and in vitro as well as in silico evaluation of chromone‐based thiosemicarbazones as potential α‐glucosidase inhibitors. In vitro experiments showed that the tested compounds were significantly more potent than the standard acarbose, with the lead compound 3n exhibiting an IC50 value of 0.40 ± 0.02 μM, ~2183‐fold higher than acarbose having an IC50 of 873.34 ± 1.67 μM. A kinetic mechanism analysis demonstrated that compound 3n exhibited reversible inhibition of α‐glucosidase. To gain deeper insights, in silico molecular docking, pharmacokinetics, and molecular dynamics simulations were conducted for the investigation of the interactions, orientation, stability, and conformation of the synthesized compounds within the active pocket of α‐glucosidase.

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Design, synthesis, in-vitro and in-silico studies of chromone‐isoxazoline conjugates as anti‐bacterial agents

Cited by 15 publications

References 65 publications

Novel carbazolyl–thiazolyl–chromone and carbazolyl–thiazolyl–pyrazole hybrids: synthesis, cytotoxicity evaluation and molecular docking studies

Novel carbazolyl–thiazolyl–chromone and carbazolyl–thiazolyl–pyrazole hybrids: synthesis, cytotoxicity evaluation and molecular docking studies

New Triazole-Isoxazole Hybrids as Antibacterial Agents: Design, Synthesis, Characterization, In Vitro, and In Silico Studies

Synthesis of the chromone‐thiosemicarbazone scaffold as promising α‐glucosidase inhibitors: An in vitro and in silico approach toward antidiabetic drug design

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