Fuctionalization of Linear and Angular Phenothiazine and Phenoxazine Ring Systems via Pd(0)/XPhos Mediated Suzuki‐Miyaura Cross‐coupling Reactions

Onoabedje, Efeturi A.; Okoro, Uchechukwu C.; Knight, David W.; Sarkar, Amitabha

doi:10.1002/jhet.2485

Cited by 14 publications

(8 citation statements)

References 51 publications

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“…The intermediates, 6-chlor-5 H -benzo[a]phenoxazin-5-one 1 and 6-chloro- 5H -naphtho[2,1-b]pyrido[2,3-e][1,4]oxazin-5-one 2 were prepared by anhydrous base catalysed coupling of 2,3-dichloro-1,4-naphthoquinone with 2-aminophenol and 2-aminopyridinol respectively at room temperature[ 12 – 14 ]. The styrylation and arylation of 6-chloro-5 H -benzo[a]phenoxazin-5-one 1 via Suzuki-Miyaura protocol supplied ( E )-6-Styryl-5 H -benzo[a]phenoxazin-5-one, 3 and 6-phenyl-5 H -benzo[a]phenoxazin-5-one 4 respectively in good yields.…”

Section: Resultsmentioning

confidence: 99%

Oxazin-5-Ones as a Novel Class of Penicillin Binding Protein Inhibitors: Design, Synthesis and Structure Activity Relationship

et al. 2016

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Penicillin binding proteins (PBPs) are normal constituents of bacterial which are absent in mammalian cells. The theoretical binding modes of known oxazin-5-ones toward the protein were used as a guide to synthesis new inhibitors. Structural studies of protein-ligand complexes revealed that conformational discrepancies of the derivatives in the protein’s binding site gave rise to the variation in their inhibition constant which ranged from 68.58 μM to 2.04 mM. Biological assay results further confirmed the antibiotic potencies of the studied compounds. Although the outcome of biological screening does not parallel computational predictions, the results obtained from both methods suggest that the oxazin-5-one derivatives are potential PBP inhibitors, hence interesting antibiotic lead agents.

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Section: Resultsmentioning

confidence: 99%

Oxazin-5-Ones as a Novel Class of Penicillin Binding Protein Inhibitors: Design, Synthesis and Structure Activity Relationship

et al. 2016

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“…All the synthesized compounds (5)(6)(7)(8)(9)(10)(11)(12) were screened for their antimicrobial activities at concentration 10 mg/mL in agar media [9]. Using Ciprofloxacin an antibacterial agent and Ketoconazole, an antifungal agent as reference drugs.…”

Section: N Antimicrobial Screeningmentioning

confidence: 99%

Synthesis and Antimicrobial Studies of 6-Aryl and 6-Anilino Benzo[a]phenoxazinones

Ocholi

Onoabedje

Egu

2020

EJCHEM

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Palladium catalyzed Suzuki-Miyaura (SM) and Buchwald – Hartwig (BH) cross-coupling reactions of some phenoxazines are reported. The precursor 9,11-diamino-6-chloro-7-oxa-8,10,12-triaza-benzo [a] anthracen-5-one was prepared by anhydrous base mediated reaction of 2,5,6-triamino-pyrimidin-4-ol and 2,3-dichloro-1,4-naphthoquinone in methanol. The molecular structures of the synthesized compounds agreed with UV/visible, FT-IR, 1H-NMR, MS and elemental analysis data. Using Ciprofloxacin and Ketoconazole as reference drugs, the compounds were screened against six (6) micro-organisms, viz: Listeria ivanovii, Staphylococcus aureus, Klebsiellapneumoniae, Escherichia coli, Candida albicans and Aspergillusnigerand were found to show significant activity against L.ivanovii and E. coli bacteria.

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“…Although PTZs shows characteristics such as excellent conjugation, redox activity, similar to quinones,there are only limited number of methods reported for C−H functionalization, [8a–d] and among which C−C bond forming approaches are only rare [9] . Furthermore, these methods have some shortcomings such as use of transition metal catalyst, [9a,b] expensive ligand, [9b] and pre‐functionalized starting materials [9d] . Thus, there is a need for development of simple, atom economic method for alkylation of quinones and PTZs.…”

Section: Introductionmentioning

confidence: 99%

Photocatalyzed Chemo‐Selective Alkylation of Quinones and Phenothiazinones with Alkyl Amides: Photophysical and Cytotoxic Activity Studies

2021

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Alkylation of naphthoquinones (NQs) and phenothiazinone (PTZs) was achieved through chemo‐selective functionalization of different mono/di‐alkyl amides in the presence of photocatalyst eosin‐y and TBHP under the influence of blue light (Blue LEDs) as an energy source, at room temperature to get the products in moderate to good yield. These highly conjugated alkylated compounds displays absorption and emission in the visible region, has potential to be used as fluorescent probes and other light harvesting materials. Insilico study revealed that some of these compounds are potential phosphodiesterase‐4B (PDE4B) inhibitors and has excellent drug like properties. Furthermore, the cytotoxic activity of alkylated quinones toward human lung cancer cell line (A549) was studied.

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Fuctionalization of Linear and Angular Phenothiazine and Phenoxazine Ring Systems via Pd(0)/XPhos Mediated Suzuki‐Miyaura Cross‐coupling Reactions

Cited by 14 publications

References 51 publications

Oxazin-5-Ones as a Novel Class of Penicillin Binding Protein Inhibitors: Design, Synthesis and Structure Activity Relationship

Oxazin-5-Ones as a Novel Class of Penicillin Binding Protein Inhibitors: Design, Synthesis and Structure Activity Relationship

Synthesis and Antimicrobial Studies of 6-Aryl and 6-Anilino Benzo[a]phenoxazinones

Photocatalyzed Chemo‐Selective Alkylation of Quinones and Phenothiazinones with Alkyl Amides: Photophysical and Cytotoxic Activity Studies

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