Mohsen A.-M. Gomaa "Synthesis, Characterization and Antimicrobial Study of Substituted Benzopyranone Derivatives" Chem. Sci. Trans. 2(3), 964-968 (2013) (original) (raw)
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Novel derivatives of substituted bezopyran-2-ones are synthesized by catalytic reactions under refluxing conditions. 4-Hydrazinyl-3-nitrobenzopyran-2-one 4 is synthesized from 4-hydroxybenzopyran-2-one 1 via three steps reaction. By condensation reaction of 4hydrazinyl-3-nitrobenzopyran-2-one 4 and aromatic aldehydes, corresponding 4-(Nbenzylidene-hydrazino)-3-nitrobenzopyran-2-ones 5(a-c) are obtained. Cyclization reaction of 4-hydroxybenzopyran-2-one 1 with aromatic aldehydes and malononitrile, in the presence of SDS, resulted by formation of 2-amino-5-oxo-4-phenyl-(4H, 5H) pyrano-[3,2-c]-chromen-3-carbonitrile derivatives 6(a-c), whereas by reacting of 4hydroxybenzopyran-2-one 1 and aromatic aldehydes, in presence of SDS, corresponding 3,3'-(benzylidene)-bis-4-hydroxyibenzopyran-2-ones 7(a-c) are synthesized. The synthesized products are characterized on the basis of spectrometric data. Antimicrobial activity of products 5(a-c), 6(a-c) and 7(a-c) against S. aurous, E. coli and Klebsiella are investigated measuring of inhibition zones around the discs which are marked with their N, N-DMF solutions. Compounds of series 5 and 6 showed considerable antimicrobial activity against these microorganisms, whereas compounds of series 7 showed moderate activity. Impact of the substituents in antimicrobial activity also is investigated.
ISRN Medicinal Chemistry, 2013
A series of pyrano[4,3-b][1]benzopyranones (7a–t) were synthesized through hetero-Diels-Alder reaction of substituted 3-formylchromones (5) with enol ethers (6), characterized by IR, 1H NMR, 13C NMR, and mass spectral techniques. All the compounds were evaluated for antimicrobial activity against various bacterial and fungal strains, found to possess significant inhibitory potential, particularly, compounds bearing electron withdrawing group -fluoro such as 7i and 7h. Compounds were also tested and displayed a significant inhibitory potential against methicillin-resistant Staphylococcus aureus (MRSA).
International Journal of Chemical Studies, 2016
Synthesis of the new substituted 3-nitro-2H-[1]-benzopyran-2-one derivatives is presented in this study. By condensation of 4-Chloro-3-nitro-2H-1-benzopyran-2-one 2 and corresponding arylamines 3(a-b), 4(4’-carboxyphenylamino)-3-nitro-2H-[1]-benzopyran-2-one 4a and 4-(4’phenylsulphonylamino)-3-nitro2H-[1]-benzopyran-2-one 4b are synthetized in high yield. Catalytic condensation of product 2 and pyridylamines 3(c-d), afforded novel substitued 4-pyridylamino-3-nitro-2H-[1]-benzopyran-2-ones 4(cd). Alkali hydrolysis of 4(a-d) afforded the 2-hydroxy-ω-nitroacetophenone 5. The synthesized products are characterized on the basis of spectrometric data. Antibacterial activity of the compounds 4(a-d) against S. aureus, E. coli and Klebsiella was examined by measuring the inhibition zones around the disks marked with the corresponding product solutions in N,N-DMF concentration 2 mg/mL, 4 mg/mL and 6 mg/mL and results are submitted. Compounds 4c and 4a were more active against S. Aureus, 4d an...
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American Scientific Research Journal for Engineering, Technology, and Sciences, 2016
Novel derivatives of benzopyran-2-ones are synthesized by catalytic condensation reaction. 4-(3-Hydroxy-2-pyridinylamino)- 3-nitro-2H-[1]-benzopyran-2-one 4a , 4-(4-methyl-3-nitro-2-pyridinylamino)-3-nitro-2H-[1]-benzopyran-2-one, 4b and 4-(pyrimidinylamono)-3-nitro-2H-[1]-benzopyran-2-ones 4(c, d) are synthesized by condensation of 4-Chlor-3-nitro-2H-[1]-benzopyran-2-one 2 and corresponding heteroarylamines 3(a-d ) under reflux reaction conditions. Alkali hydrolysis of 4(a-d ) afforded the 2-hydroxy- ω -nitroacetophenone 5 . Structural characterization of the synthesized products is done on the basis of spectrometric data. Antibacterial activity of the compounds 4(a-d) against S. aureus , E. coli and Klebsiella was examined by measuring the inhibition zones around the disks marked with the corresponding product solutions in N,N-DMF concentration 2 mg/mL , 4 mg/mL and 6 mg/mL. Compounds 4a and 4c have shown significant antibacterial activity against S. aureus , compounds 4b and ...
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