Design and synthesis of highly oxygenated furo[3,2‐c]pyran‐4‐ones and furo[3,2‐c]chromen‐4‐ones scaffold as anticancer and antimicrobial agents

Abstract

Synthesis of a number of highly oxygenated furo [3,2-c]pyran/chromen-4-one has been accomplished by one-pot reaction from easily available dehydroacetic acid/3-acetyl-4-hydroxycoumarin or their chalcones and α-bromoketones. All the synthesized molecules were characterized utilizing various spectroscopic techniques and screened for anticancer activity (in vitro) against three colon (HCT-116, SW-620, HT-24), lung (A-549), prostate-(PC-3), breast (MCF-7) cell lines. Compounds 5a, 9d, 9f showed good activity against breast MCF-7 cancer cell line having IC 50 values 6.9, 2.8, 5.3 μM, respectively. Of these compounds, 9d showed better activity against prostate PC-3 cell line with IC 50 value 3.8 μM. The synthesized compounds were also studied for antibacterial activity (in vitro) using different strains of bacteria (Bacillus subtilis and Staphylococcus aureus -Gram-positive and Escherichia coli, Pseudomonas aeruginosa -Gram negative) as well as fungal strains (Aspergillus niger and Candida albicans) using Norfloxacin and Fluconazole as antibacterial and antifungal standard drugs, respectively. The antimicrobial screening study showed that compound 9f exhibited promising activity against S. aureus and B. subtilis, while 5h showed excellent and 5i and 9b showed better activity against E. coli. Compounds 5d and 5e showed promising activity against P. aeruginosa. The compounds 5c-5e displayed excellent activity against C. albicans and A. niger than Fluconazole.

Synthesis of arene-functionalized fused heterocyclic scaffolds via a regioselective cascade 1,4-conjugate addition/5-exo-dig annulation strategy

“…6 Kumar and co-workers described an efficient microwave-assisted reaction of dehydroacetic acid and its chalcones with α-bromoketones to produce acetyl-functionalized furo[3,2- c ]pyran-4-ones, and evaluated their in vitro antimicrobial activities (Scheme 1b). 7 Recently, an improved one-pot synthetic pathway involving Fe-catalyzed multicomponent reactions of 4-hydroxy-2 H -pyran-2-ones, 2-methylfurans and aldehydes was reported for the modular assembly 2,3-disubstituted furo[3,2- c ]pyran-4-ones (Scheme 1c). 8 However, the synthesis of highly sterically congested 3-phenolic furo[3,2- c ]pyran-4-ones has been documented in very limited reports.…”