Synthesis of a new series of 2-(2-oxo-2H-chromen-3-yl)-5H-chromeno[4,3-b]pyridin-5-ones by two facile methods and evaluation of their antimicrobial activity

Patel, Apoorva A.; Lad, Hemali B.; Pandya, Kinnar R.; Patel, Chirag; Brahmbhatt, D. I.

doi:10.1007/s00044-013-0489-4

Cited by 62 publications

(35 citation statements)

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“…Brahmbhatt et al have demonstrated a proper method for ring closure using these two sites. [13] Furthermore, this molecule is a convenient starting material for the 1,3-dipolar cycloaddition reaction due to its unsaturated double bond. As we know, 1,3dipolar cycloaddition reaction is an efficient method for the synthesis of pyrazole derivatives.…”

Section: Resultsmentioning

confidence: 99%

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Design and Synthesis of Coumarin‐Based Pyrazolopyridines as Biocompatible Fluorescence Dyes for Live‐Cell Imaging

et al. 2020

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An unprecedented strategy for the synthesis of highly fluorescent chromeno[4,3-b]pyrazolo[3,4-d]pyridin-4(3H)-ones via a 1,3-dipolar cycloaddition reaction/ring closure in the presence of NH 4 OAc/air oxidation in a one-pot procedure is described. The molecular structures were characterized by IR spectrophotometry, mass spectrometry, NMR spectroscopy, and single-crystal X-ray analysis. Furthermore, the photophysical properties of synthesized compounds were studied by absorption and fluorescence spectroscopy. All of the compounds exhibited almost similar spectra due to their resembling molecular structures. Therefore, one of the synthesized coumarin-based pyrazolopyridines was selected to evaluate its application as a live-cell imaging agent by an inverted phasecontrast microscope. The result reveals that synthesized chromeno[4,3-b]pyrazolo[3,4-d]pyridin-4(3H)-one has acceptable photostability, low cytotoxicity, satisfactory fluorescence efficiency (Φ f : 0.53), and excellent capability to penetrate into the intracellular space. Accordingly, it can be rendered as a promising dye in fluorescence bioimaging. Chemoselectivity, simple and available starting materials, operational simplicity, and good yields are other outstanding advantages of this reaction.

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Section: Resultsmentioning

confidence: 99%

“…Supporting information includes experimental details, analysis data, copies of IR, 1 H, 13 C NMR, and Mass spectra of products, crystal structure determination, and refinement.…”

Section: Supporting Information Summarymentioning

confidence: 99%

Design and Synthesis of Coumarin‐Based Pyrazolopyridines as Biocompatible Fluorescence Dyes for Live‐Cell Imaging

et al. 2020

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“…162 In 2013 Brahmbhatt and co-workers reported the synthesis of a molecule which incorporates both pyridyl-substituted and pyrido-fused 2H-chromen-2-ones. 163 They developed a one-pot, three-component reaction of precursor 3-[(ethylamino)methyl]-4-hydroxy coumarins 216 and pyridinium salts 217 in the presence of ammonium acetate, yielding 2-(2-oxo-2H-chromen-3-yl)-5H-chromeno[4,3-b]-pyridin-5-ones 220 in moderate to good yields (Scheme 69). The reaction pathway involved the decomposition of the starting Mannich base to form a coumarin methide 218, which reacts with salt 217 in the presence of ammonium acetate, to obtain a 1,5-dicarbonyl intermediate 219 that nally gets converted into the expected product by Krohnke's reaction.…”

Section: Synthesis Of Coumarin-linked and Coumarin-fused Heterocyclesmentioning

confidence: 99%

Coumarin heterocyclic derivatives: chemical synthesis and biological activity

et al. 2015

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“…A. Patel et al . synthesised a series of novel 2‐(2‐oxo‐2 H‐ chromen‐3‐yl)‐5 H ‐chromeno[4,3‐ b ]pyridin‐5‐ones 71 using two methodologies (Scheme ) [Mannich base of 4‐hydroxy‐coumarin and 4‐chloro‐3‐formyl coumarin 70 ].…”

Section: Synthesis Of Pyridocoumarinsmentioning

confidence: 99%

A Concise Review on Pyridocoumarin/Azacoumarin Derivatives: Synthesis and Biological Activity

Patra¹

2019

ChemistrySelect

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Coumarins are important due to their versatile bio‐activity. Synthesised pyridocoumarin derivatives show remarkable biological activities including antifungal, antibacterial, antitumor, antiHIV, and antimicrobial activity. The present review aims to review a vast body of literature on different synthetic methodology mainly aza‐Diels Alder reaction, metal catalyzed cyclization and multicomponent reaction and bioactivity of pyridocoumarin derivatives as published during the period from 1997 up to 2017. The synthesised compounds have been reported in literature either by construction of pyridine, pyran or of both ring starting from suitable precursors.

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Synthesis of a new series of 2-(2-oxo-2H-chromen-3-yl)-5H-chromeno[4,3-b]pyridin-5-ones by two facile methods and evaluation of their antimicrobial activity

Cited by 62 publications

References 25 publications

Design and Synthesis of Coumarin‐Based Pyrazolopyridines as Biocompatible Fluorescence Dyes for Live‐Cell Imaging

Design and Synthesis of Coumarin‐Based Pyrazolopyridines as Biocompatible Fluorescence Dyes for Live‐Cell Imaging

Coumarin heterocyclic derivatives: chemical synthesis and biological activity

A Concise Review on Pyridocoumarin/Azacoumarin Derivatives: Synthesis and Biological Activity

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