Synthesis and characterization of oxazine bearing pyridine scaffold as potential antimicrobial agents

Desai, N. C.; Bhatt, Nayan; Joshi, Surbhi B.; Vaja, Darshita V.

doi:10.1080/00397911.2017.1377734

Cited by 9 publications

(3 citation statements)

References 17 publications

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“…Electron donating group substitution on benzene ring showed lesser potency than electron withdrawing group. Presence of 3,4,5‐trimethoxy group on benzene ring showed excellent activity against C. albicans with MIC value 12.5 μg/ml [47] …”

Section: Biological Activities Of 13‐oxazine Derivativesmentioning

confidence: 99%

“…Presence of 3,4,5-trimethoxy group on benzene ring showed excellent activity against C. albicans with MIC value 12.5 μg/ ml. [47] Rbaa et al in 2019 synthesized six oxazino derivatives of 8hydroxyquinoline and evaluated them for antibacterial activity against six pathogenic strains namely, E. cloacae, E. coli, K. pneumonia, S. aureus, P. aeruginosa and A. baumanii. The MIC for all the compounds was calculated and compared with three standard antibiotics including Penicillin G, Norfloxacin and Erythromycin by disk diffusion technique against all the used bacterial strains.…”

Section: Anti-bacterial Activity Of 13-oxazine Derivativesmentioning

confidence: 99%

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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: Biological Activities Of 13‐oxazine Derivativesmentioning

confidence: 99%

Section: Anti-bacterial Activity Of 13-oxazine Derivativesmentioning

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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“…Simple examples of dioxazines include naturally occurring cinnabarine and cinnabaric acid, which are derived from tryptophan biodegradation [7]. Oxazines play an important role as antihyperglycemic [8], antileishmanial [9], antitubercular [10,11], antiulcer [12], anticancer [13,14] and antibacterial [15]. Patil and his coworkers were synthesized some derivatives of oxazines and some compounds showed moderate potent antibacterial activity while some others showed potent activity towards E.coli, S. aureus, Micrococcus and B. subtilis bacterial strains [16].…”

Section: Introductionmentioning

confidence: 99%

Molecular Docking and DFT Study of Synthesized Oxazine Derivatives

et al. 2021

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Molecular docking and DFT calculation have been investigated for the synthesized oxazine derivatives. Theoretical calculations including DFT study has investigated and proved the reactivity of compound 4 is the greatest among others as follow 4>2>5>3>1. On the other hand, the stability of compounds has been calculated to prove that compound 1 has the highest stability among others as follow 1>3>5>2>4. Antibacterial activity test was confirmed potent activity for all the synthesized derivatives against E. coli and S. aureus bacterial strains. The synthesized compounds including 2, 4 and 5 showed potent inhibitory activity against both bacterial strains compared to positive reference of tetracycline. Docking study revealed that oxazine derivatives with 4-chlorobenzamide group at position number 2 showed higher potency than tetracycline as antibacterial by inhibiting TetR.

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Assessment of Dihydro[1,3]oxazine‐Fused Isoflavone and 4‐Thionoisoflavone Hybrids as Antibacterials

et al. 2021

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A series of isoflavone functionalized 3,4‐dihydro‐1,3‐oxazine hybrids was synthesized in good to excellent yields through a Mannich‐type condensation cyclization reaction of 6‐chloro‐7‐hydroxy‐3‐(2‐methoxy‐phenyl)‐chromen‐4‐one or 6‐chloro‐7‐hydroxy‐3‐(2‐methoxy‐phenyl)‐chromene‐4‐thione with formaldehyde and primary amines. After spectroscopic characterization, these newly prepared hybrids were evaluated for their antibacterial activities against two of each Gram positive (Staphylococcus aureus and Bacillus subtilis) and Gram negative (Escherichia coli and Pseudomonas aeruginosa) bacterial strains. Among the screened compounds, dihydro[1,3]oxazine‐fused 4‐thionoisoflavones(9 band9 c) exhibited potent inhibitory activity against all the tested bacterial species. Moreover, compound 9 b possessed most promising antibacterial activity against P. aeruginosa and B. subtiliswith MIC 16 μg/mL and S. aureusand E. coliwith MIC 32 μg/mL. Further, 9 bdemonstrated better efficacy (MIC=16 μg/mL) than the standard drug ampicillin (MIC=32 μg/mL) against P. aeruginosaand it also found to be equipotent (MIC=16 μg/mL) as ampicillin against B. subtilis. Considering the disk diffusion and synergistic studies, 9 bemerged asmost active compound showing potent activity against all the tested bacterial strains. In addition, no significant hemolysis or cytotoxicity was observed towards human embryonic kidney (HEK293)cells as well as Galleria mellonellalarvae (in vivo). Hence, compound 9 bhas potential to be further explored alone and in combination with ampicillin as a next generation antibacterial agent.

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Synthesis and characterization of oxazine bearing pyridine scaffold as potential antimicrobial agents

Cited by 9 publications

References 17 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

Molecular Docking and DFT Study of Synthesized Oxazine Derivatives

Assessment of Dihydro[1,3]oxazine‐Fused Isoflavone and 4‐Thionoisoflavone Hybrids as Antibacterials

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