Synthesis, in vitro and in silico studies of naphto-1,3-oxazin-3(2H)-one derivatives as promising inhibitors of cholinesterase and α-glucosidase

Boudebbous, Khawla; Boulebd, Houssem; Derabli, Chamseddine; Bendjeddou, Lamia; Bensouici, Chawki; Harakat, Dominique; Mérazig, Hocine; Debache, Abdelmadjid

doi:10.1016/j.molstruc.2020.129103

Cited by 8 publications

(2 citation statements)

References 71 publications

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“…In Silico studies including Hirshfeld surface, DFT calculations, docking study and ADME properties in order to get insights into the molecular structure, structureactivity relationship, chemical reactivity and bioavailability of the synthesized compounds showed that these compounds exhibit significant AChE, BChE, and α-glucosidase inhibitory activities and results are in good agreement with the in vitro studies. [67]…”

Section: Cholineestrase and Alpha-glucosidase Enzyme Inhibition Activ...mentioning

confidence: 99%

1,3‐Oxazine as a Promising Scaffold for the Development of Biologically Active Lead Molecules

Gupta,

Saini,

Basavarajaiah

et al. 2023

ChemistrySelect

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Heterocyclic compounds form an important part of wide range of biologically active molecules. The heteroatom provides them specificity for various receptors. 1,3‐oxazine has been considered as a privileged scaffold in many medicinal chemistry applications. Compounds having 1,3‐oxazine moiety exhibit broad range of biological applications such as anticancer, antimicrobial, anti‐inflammatory, antiplatelet, antitubercular and alpha‐glucosidase inhibition activities. In this review, we consolidate the recent developments in the synthesis and biological activities of 1,3‐oxazine containing compounds. Also, the structure activity relationship (SAR) studies of different derivatives exhibiting several biological activities are summarized. Database such as Science direct, Pubmed and Google scholar were searched using keywords ‘1,3‐Oxazine’, ‘synthesis’, ‘derivatives’, and ‘biological activities’. The review would provide a lead for the development of competent candidates with 1,3‐oxazine moiety having broad range of applications in the treatment of several human disorders.

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Section: Cholineestrase and Alpha-glucosidase Enzyme Inhibition Activ...mentioning

confidence: 99%

1,3‐Oxazine as a Promising Scaffold for the Development of Biologically Active Lead Molecules

Gupta,

Saini,

Basavarajaiah

et al. 2023

ChemistrySelect

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“…Due to their diverse and extensive biological activities, oxazine derivatives have garnered signi cant attention in the eld of organic synthesis. Recently, many efforts have been made to create e cient methods for synthesizing oxazine using diverse catalytic methodologies anchored upon catalysts including phenylboronic acid [19] [20], graphene oxide [21], [bmim]Br [22], 4-hydroxypyridinium tetrachloride/silica gel [23], tetramethyl ammonium hydroxide [24], ZnO [25], Propylphosphonic Anhydride [26], silica-bonded S-sulfonic acid, p-TsOH [27], Cu, GO-Fe3O4-Ti (IV) [28], and TiCl 4 [29]. However, the methods mentioned in the literature have disadvantages such as di cult reaction conditions, toxic and expensive catalysts and di culties in processing the reactions.…”

Section: Introductionmentioning

confidence: 99%

Advanced Catalytic Syntheses of 1,3-Oxazine Derivatives via Electrophilic Substitution Using Mono- and Bimetallic Phosphate Catalysts: Co₃(PO 4 ) 2 and CoCa 3 (HPO 4 )(PO 4 ) 2 (OH)

hallaoui,

FERRAA,

MERROUN

et al. 2024

Preprint

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This research introduces a novel catalytic approach for the synthesis of 1,3-oxazinone derivatives through a multicomponent reaction that relies on an electrophilic substitution mechanism, employing two cobalt-based phosphate catalysts. This approach, allowed us to synthesize oxazine derivatives, known for their significant biological activities, achieving impressive yields of up to 97% in a remarkably short time of only 7 minutes, all under conditions environmentally friendly according to the principles of green chemistry using the ethanol/water mixture as a green solvent. In our study, we utilized two catalysts derived from cobalt-modified phosphate, which were synthesized in our laboratory using simple methods. The first support consists of a monometallic catalyst, denoted as Co3(PO4)2, whereas the second is a bimetallic phosphate catalyst modified with cobalt and calcium CoCa3(HPO4)(PO4)2(OH). Our developed methods had various advantages including simplicity of the process, rapid reaction time, simple clean-up, ability to recover and reuse the catalyst and overall simplicity. All these advantages render this developed approach effective and viable for synthesizing oxazine derivatives suitable for large-scale applications.

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Flavone-1,2,3-triazole derivatives as potential α-glucosidase inhibitors: Synthesis, enzyme inhibition, kinetic analysis and molecular docking study

Dhameja

Kumar

Kurella

et al. 2022

Bioorganic Chemistry

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Synthesis, in vitro and in silico studies of naphto-1,3-oxazin-3(2H)-one derivatives as promising inhibitors of cholinesterase and α-glucosidase

Cited by 8 publications

References 71 publications

1,3‐Oxazine as a Promising Scaffold for the Development of Biologically Active Lead Molecules

1,3‐Oxazine as a Promising Scaffold for the Development of Biologically Active Lead Molecules

Advanced Catalytic Syntheses of 1,3-Oxazine Derivatives via Electrophilic Substitution Using Mono- and Bimetallic Phosphate Catalysts: Co₃(PO 4 ) 2 and CoCa 3 (HPO 4 )(PO 4 ) 2 (OH)

Flavone-1,2,3-triazole derivatives as potential α-glucosidase inhibitors: Synthesis, enzyme inhibition, kinetic analysis and molecular docking study

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