Rational design and synthesis of novel 2-(substituted-2H-chromen-3-yl)-5-aryl-1H-imidazole derivatives as an anti-angiogenesis and anti-cancer agent

Gopinath, Gudipudi; Sagurthi, Someswar Rao; Shyam, Perugu; Garlapati, Achaiah; Krupadanam, G. L. David

doi:10.1039/c4ra09945a

Cited by 22 publications

(11 citation statements)

References 43 publications

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“…3-Bromo-1,3,4,5-tetrahydro-2 H -benzo[ b ]azepin-2-one was purchased from Ark Pharm. 2-Bromo-1-(2,4-dichlorophenyl)ethan-1-one and 1-(2,4-dichlorophenyl)-2-iodoethan-1-one were prepared by heating a 0.2 M dry acetone solution of 2-chloro-1-(2,4-dichlorophenyl)ethan-1-one at 70 °C in a thick-walled sealed reaction vessel with 1.5 equiv of sodium bromide and sodium iodide, respectively, and spectral data was in agreement with the literature 56,57 . 2,2-Dibromo-1-phenylethan-1-one was prepared as previously reported 58 .…”

Section: Methodssupporting

confidence: 76%

Organopolymer with dual chromophores and fast charge-transfer properties for sustainable photocatalysis

et al. 2019

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Photocatalytic polymers offer an alternative to prevailing organometallics and nanomaterials, and they may benefit from polymer-mediated catalytic and material enhancements. MPC-1 , a polymer photoredox catalyst reported herein, exhibits enhanced catalytic activity arising from charge transfer states (CTSs) between its two chromophores. Oligomeric and polymeric MPC-1 preparations both promote efficient hydrodehalogenation of α -halocarbonyl compounds while exhibiting different solubility properties. The polymer is readily recovered by filtration. MPC-1 -coated vessels enable batch and flow photocatalysis, even with opaque reaction mixtures, via “backside irradiation.” Ultrafast transient absorption spectroscopy indicates a fast charge-transfer process within 20 ps of photoexcitation. Time-resolved photoluminescence measurements reveal an approximate 10 ns lifetime for bright valence states. Ultrafast measurements suggest a long CTS lifetime. Empirical catalytic activities of small-molecule models of MPC-1 subunits support the CTS hypothesis. Density functional theory (DFT) and time-dependent DFT calculations are in good agreement with experimental spectra, spectral peak assignment, and proposed underlying energetics.

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Section: Methodssupporting

confidence: 76%

Organopolymer with dual chromophores and fast charge-transfer properties for sustainable photocatalysis

et al. 2019

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“…Synthesis of imidazo[1, 5‐a]pyridine derivatives with different donors is depicted in Scheme . 2‐Benzoylpyridine ( 1 ), salicylaldehyde ( 1 d ), 2‐methoxy benzaldehyde ( 1 e ) and 4‐(diethylamino)‐2‐hydroxy benzaldehyde ( 1 b ) are commercially available whereas 8‐hydroxy‐1,2,3,5,6,7‐hexahydropyrido[3, 2,1‐ij]quinoline‐9‐carb‐aldehyde ( 1 a ) and 2,4‐hydroxy benzaldehyde ( 1 c ) were prepared according to the procedure as described in literature ,. The dyes 2 a‐e were synthesized by condensation of 2‐benzoyl pyridine and substituted aldehydes in presence of ammonium acetate and glacial acetic acid as a reaction solvent at 110° C. The synthesized dyes 2 a‐e were fully characterized by 1 H NMR, 13 C NMR, and mass spectra.…”

Section: Resultsmentioning

confidence: 99%

Tuning ‘Stokes Shift’ and ICT Character by Varying the Donor Group in Imidazo[1,5 a]pyridines: A Combined Optical, DFT, TD‐DFT and NLO Approach

Mohbiya

Sekar

2018

ChemistrySelect

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Imidazo [1, 5a]pyridine based novel donor-acceptor dyes (2a-e) with the large Stokes shift (ca. 140-200 nm) were synthesized and characterized. We report on the steady-state and nanosecond time-resolved emission studies of 2a-e in different microenvironments which reveal that the dyes 2a-c (average lifetime of 0.65, 1.36 and 1.63 ns respectively) perform reversible proton motion in chloroform due to variable donor group present at the para position of substituted phenyl group attached to imidazopyridine core as an acceptor group whereas 2d and 2e (average lifetime of 3.50 and 4.06 ns respectively) compete with 2a-c in agreement with considerable intramolecular charge transfer (ICT) characteristics. Solvent polarity plots viz. Lippert-Mataga, McRae, and Bakhshiev equation furnish the confirmation of ICT character. Density functional theory (DFT) calculations [(B3LYP/6-311 + +G(d, p)] provide the information of structural as well as the electronic properties of dyes 2a-e. Natural bond orbital (NBO) analyses enlighten the nature of the charge or proton transfer within the selected donor-acceptor orbital interaction with the large energy of stabilization (the donor-acceptor orbital interactions increases in the order 2a > 2b > 2c > 2d > 2e). The large difference in dipole moment (ca. 1.57-21.55 D) results in a strong non-linear optical (NLO) properties. The NLO properties were evaluated theoretically as well as spectroscopically in solvents of different polarities and the resulting hyperpolarizabilities fall within the expected limiting values. These results bring new findings in coupled ICT and proton transfer reactions which will be useful for further research and promising applications in sensing polarity or H-bonding of microenvironments similar to that of the biological ones.

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“…In 2014, Krupadanam and co-workers published an acid-free, Br 2 -mediated halogenation [ 44 ]. One equivalent of bromine was added dropwise to an ice-cold solution of the substrate in diethyl ether, after which the solution was stirred for 2 h at room temperature.…”

Section: Direct α-Halogenation Of Aryl Ketonesmentioning

confidence: 99%

Synthetic Access to Aromatic α-Haloketones

et al. 2022

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α-Haloketones play an essential role in the synthesis of complex N-, S-, O-heterocycles; of which some exhibit a remarkable biological activity. Research further illustrated that α-bromo-, α-chloro-, and α-iodoketones are key precursors for blockbuster pharmacological compounds. Over the past twenty years, substantial advances have been made in the synthesis of these industrially relevant building blocks. Efforts have focused on rendering the synthetic protocols greener, more effective and versatile. In this survey, we summarised and thoroughly evaluated the progress of the field, established in the past two decades, in terms of generality, efficacy and sustainability.

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Rational design and synthesis of novel 2-(substituted-2H-chromen-3-yl)-5-aryl-1H-imidazole derivatives as an anti-angiogenesis and anti-cancer agent

Abstract: Based on the earlier proven pharmacophore analogues of cancer a novel 2-(substituted-2H-chromen-3-yl)-5-aryl-1H-imidazoles were rationally designed, synthesized and used for competitive biological activity against cancer cell lines.

Cited by 22 publications

References 43 publications

Organopolymer with dual chromophores and fast charge-transfer properties for sustainable photocatalysis

Organopolymer with dual chromophores and fast charge-transfer properties for sustainable photocatalysis

Tuning ‘Stokes Shift’ and ICT Character by Varying the Donor Group in Imidazo[1,5 a]pyridines: A Combined Optical, DFT, TD‐DFT and NLO Approach

Synthetic Access to Aromatic α-Haloketones

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