Synthetic approaches for novel 3-heteroaryl-4-hydroxy-1-methylquinoline-2(1H)one: spectroscopic characterization, molecular docking and DFT investigations.

ABSTRACT: Ring opening and recyclization reactions with 4-hydroxy-6-methyl-3-nitro-2H-pyrano[3,2-c]quinoline-2,5(6H)-dione (1) was examined towards some carbon nucleophilic reagents. Treatment of key precursor 1 with cyanoacetamide, malononitrile dimer and 1H-benzimidazol-2-ylacetonitrile afforded pyridines 2, 3 and pyrido[1,2-a]benzimidazole 4, respectively. Reaction of compound 1 with 5-amino-2,4-dihydro-3H-pyrazol-3-one and 5-amino-3-methyl-1H-pyrazole furnished pyrazolo[3,4-b]pyridine derivatives 5 and 6. Further, pyrido[2,3-d]pyrimidines 7-9 were synthesized from recyclization of compound 1 with some 6-aminouracil derivatives. Compounds 2-4 demonstrated favorable efficacy in HepG-2 liver cancer cells comparable to reference drug (ci

SUBMITTER: Mostafa MA 

PROVIDER: S-EPMC11869377 | biostudies-literature | 2025 Feb

REPOSITORIES: biostudies-literature