A Review on Current Synthetic Strategies of Oxazines

Gaonkar, Santosh L.; Nagaraj, Vignesh U; Nayak, Swarnagouri

doi:10.2174/1570193x15666180531092843

Cited by 28 publications

(12 citation statements)

References 48 publications

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“…Some properties including, versatility of the oxazine skeleton, relative chemical simplicity and accessibility, retained these chemicals among the most promising sources of bioactive compounds [ 7 ]. Oxazine analogues were found to represent appropriate pharmacological effects such as anti-bacterial, anti-coagulant, cytotoxic, analgesic, antipyretic anticonvulsant, and anti-tumor [ 8 – 12 ]. Oxazine with naphthalene rings, called naphthoxazines have different pharmacological activities such as antiparkinson, psycho stimulating, anti-tumor, and antidepressant [ 10 ].…”

Section: Introductionmentioning

confidence: 99%

“…Hence, these compounds are an interesting category of chemical for researchers, and there is enough scope to explore new oxazine derivatives. So, many researchers have been considered to facile the synthesizing of such fundamental heterocyclic rings [ 8 ]. Several procedures for the preparation of oxazine analogous have been previously described [ 10 , 11 , 14 ].…”

Section: Introductionmentioning

confidence: 99%

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Efficient synthesis of 1,3-naphtoxazine derivatives using reusable magnetic catalyst (GO-Fe3O4–Ti(IV)): anticonvulsant evaluation and computational studies

et al. 2022

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A series of 2-aryl/alkyl-2,3-dihydro-1H-naphtho[1,2-e][1,3]oxazines (S1–S11) were synthesized with an eco-friendly and recoverable nanocatalyst (GO-Fe3O4–Ti(IV)) as an efficient magnetic composite. The new nanocatalyst was characterized by FT-IR, XRD and, EDS analysis. A conformable procedure, easy to work up and having a short reaction time with high yields are some advantages of this method. The new catalyst is also thermal-stable, reusable and, environment-friendly. The chemical structures of the synthesized 1,3-oxazine compounds were confirmed by comparing their melting points with those reported in literature. Then, the anticonvulsant activity of these compounds was assessed by the intraperitoneal pentylenetetrazole test (ipPTZ). Compounds S10 and S11 displayed considerable activity against chemically-induced seizure tests. The molecular simulation was also done to achieve their binding affinities as γ‐aminobutyric acid A (GABA‐A) receptor agonists as an assumptive mechanism of their anticonvulsant action. The result of molecular studies represented strongly matched with biological activity. Molecular docking simulation of the potent compound (S10) and diazepam as the positive control was performed and some critical residues like Thr262, Asn265, Met286, Phe289, and Val290 were identified. Based on the anticonvulsant results and also in silico ADME predictions, S11 can be to become a potential drug candidate as an anticonvulsant agent.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Efficient synthesis of 1,3-naphtoxazine derivatives using reusable magnetic catalyst (GO-Fe3O4–Ti(IV)): anticonvulsant evaluation and computational studies

et al. 2022

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“…Oxazines and their derivatives are heterocyclic compounds containing one oxygen atom and one nitrogen atom ( Figure 2 ) [ 10 ]. These heterocycles have special interest because they constitute an important class of non-natural and natural products, which display useful biological properties [ 11 , 12 , 13 ] as well as interesting photophysical and lasing properties [ 14 , 15 ].…”

Section: Introductionmentioning

confidence: 99%

Decoration of A-Ring of a Lupane-Type Triterpenoid with Different Oxygen and Nitrogen Heterocycles

et al. 2022

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Betulinic acid (BA) was used as starting building block to create a library of novel BA-derived compounds containing O- and N-heterocycles. Firstly, BA was converted into methyl betulonate (BoOMe), which was used as intermediate in the developed methodologies. 1,2-Oxazine-fused BoOMe compounds were obtained in 12–25% global yields through a Michael addition of nitromethane to methyl (E)-2-benzylidenebetulonate derivatives, followed by nitro group reduction and intramolecular cyclization. Remarkably, the triterpene acts as a diastereoselective inducer in the conjugate addition of nitromethane, originating only one diastereomer out of four possible ones. Furthermore, other oxygen and nitrogen-containing heterocycles were installed at the A-ring of BoOMe, affording 2-amino-3-cyano-4H-pyran-fused BoOMe, diarylpyridine-fused BoOMe and 1,2,3-triazole–BoOMe compounds, using simple and straightforward synthetic methodologies. Finally, BA was revealed to be a versatile starting material, allowing the creation of a molecular diversification of compounds containing a triterpenic scaffold and O- and N-heterocycles.

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“…Nitrones have been widely used as precursors for the synthesis of enantiopure organic compounds endowed with important biological activities such as the heterocyclic isoxazolines [5], isoxazolidines [6][7][8][9], oxazines [10] derivatives and other natural products [11]. In turn, the isoxazolidine functional group, obtained by 1,3-dipolar cycloaddition between a nitrone and an alkene, plays a crucial role in several chemical transformations due to the lability of the N-O bond [12].…”

Section: Introductionmentioning

confidence: 99%

Multifunctional isoxazolidine derivatives as α-amylase and α-glucosidase inhibitors

Ghabi

Brahmi

Alminderej

et al. 2020

Bioorganic Chemistry

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A Review on Current Synthetic Strategies of Oxazines

Cited by 28 publications

References 48 publications

Efficient synthesis of 1,3-naphtoxazine derivatives using reusable magnetic catalyst (GO-Fe3O4–Ti(IV)): anticonvulsant evaluation and computational studies

Efficient synthesis of 1,3-naphtoxazine derivatives using reusable magnetic catalyst (GO-Fe3O4–Ti(IV)): anticonvulsant evaluation and computational studies

Decoration of A-Ring of a Lupane-Type Triterpenoid with Different Oxygen and Nitrogen Heterocycles

Multifunctional isoxazolidine derivatives as α-amylase and α-glucosidase inhibitors

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