Synthesis of 2-aroylfuro[3,2-c]quinolines from quinolone-based chalcones and evaluation of their antioxidant and anticholinesterase activities
authors Ferreira, JPS; Cardoso, SM; Paz, FAA; Silva, AMS; Silva, VLM
nationality International
journal NEW JOURNAL OF CHEMISTRY
keywords FUROQUINOLINE ALKALOIDS; DERIVATIVES; INHIBITORS; COUMARINS; STEMS
abstract An elegant synthesis of 2-aroylfuro[3,2-c]quinolines 2a-e from quinolone-based chalcones 1a-evia bromination of the exocyclic double bond followed by furan ring formation was developed. Interestingly, during bromination the tautomerization of the quinolin-4(1H)-one ring of compounds 1a-e into the corresponding 4-hydroxyquinoline occurred followed by cyclization to give in a one-pot transformation, upon in situ oxidation, the 2-aroylfuro[3,2-c]quinolines 2a-e. In the bromination of the quinolone-based chalcone 1e, bearing a hydroxy group at the ortho-position of the aryl ring, two compounds were obtained; the major one was the expected 2-aroylfuro[3,2-c]quinoline 2e dibrominated in the aryl ring, due to the activating effect of the hydroxy group, and the minor was identified as 12a-bromo-6b,12a-dihydro-12H-chromeno[2 ',3 ':4,5]furo[3,2-c]quinolin-12-one 3. Two possible mechanistic pathways were proposed to explain the formation of compound 3. The structures of all new compounds were confirmed by H-1 and C-13 NMR, ESI and HRMS spectra. Compounds 2a-e and 3 showed no significant scavenging activity towards the free radicals ABTS(+)& x2d9; and NO & x2d9;, but compounds 2a and 2c showed promising activity as acetylcholinesterase inhibitors (IC50 = 78.99 +/- 2.75 mu M and 27.52 +/- 0.23 mu M, respectively).
publisher ROYAL SOC CHEMISTRY
issn 1144-0546
isbn 1369-9261
year published 2020
volume 44
issue 16
beginning page 6501
ending page 6509
digital object identifier (doi) 10.1039/d0nj00409j
web of science category Chemistry, Multidisciplinary
subject category Chemistry
unique article identifier WOS:000531201500042
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