Synthesis of New Fused Heterocyclic 2-Quinolones and 3-Alkanonyl-4-Hydroxy-2-Quinolones

Abstract

Herein, we report the synthesis of 5,12-dihydropyrazino[2,3-c:5,6-c′]difuro[2,3-c:4,5-c′]-diquinoline-6,14(5H,12H)diones, 2-(4-hydroxy-2-oxo-1,2-dihydroquinolin-3-yl)-1,4-diphenyl- butane-1,4-diones and 4-(benzo-[d]oxazol-2-yl)-3-hydroxy-1H-[4,5]oxazolo[3,2-a]pyridine-1-one. The new candidates were synthesized and identified by different spectroscopic techniques, and X-ray crystallography.

Synthesis of potentially new schiff bases of N-substituted-2-quinolonylacetohydrazides as anti-COVID-19 agents

“…We also synthesized naphthofuro[3,2- c ]quinoline-6,7,12-trione VI, and pyrano[3,2- c ]quinoline-6,7,8,13-tetraone, VII that have shown potential as ERK inhibitors [32] , whereas synthesis of bis(6-substituted-4-hydroxy-2-oxo-1,2-dihydroquinolin-3-yl)naphtha-ene-1,4-dione VIII and (substituted N -(alkyl)bis-quinolinone)-triethylammonium salt VIV [33] , were explored as candidates for extracellular signal-regulated kinases 1/2 (ERK1/2) having antineoplastic activity [33] . Recently, we have reported the synthesis of 5,12-dihydro-pyrazino[2,3- c :5,6- c' ]difuro[2,3- c :4,5- c' ]-diquinoline-6,14( 5 H,12 H )-dione X [34] and 2-(4-hydroxy-2-oxo-1,2-dihydroquinolin-3-yl)-1,4-diphenyl-butane-1,4-dione XI [34] . Most indicative is our recent synthesis of 6-substiuted-4-(2-(4-substituted-benzylidene)hydrazinyl)quinolin-2(1H)-one derivative XII [35] which was evaluated for their in vitro cytotoxic activity against 60 cancer cell lines according to NCI protocol [35] .…”

Greening Solid-Phase Organic Synthesis: Environmentally Conscious Synthesis of Pharmaceutically Relevant Privileged Structures 5,6-Dihydropyridin-2(1H)-ones and Quinolin-2(1H)-ones

“…Selected structures of interest, similar to our target structures (14−16), such as 4-benzyloxyquinolin-2-(1H)-one derivatives 9 were identified as potential anticancer agents, 27 substituted 2-quinolones 10 showed anti-HIV activity, 28 and fluorinated 4-hydroxyquinolin-2(1H)-one 11 exhibited photoantiproliferative activity. 29 Additionally, 4-hydroxy-2-quinolones are versatile intermediates in the synthesis of a vast number of more complex biologically active heterocyclic compounds 30 (and references cited therein) including alkaloids furoerioaustralasine 12 31 and flindersine 13. 32 Beside that, they also serve as a coupling component in the preparation of azo dyes.…”