Synthesis, Characterization, Anticancer and Antibacterial Activity of Some Novel Pyrano[2,3-d]pyrimidinone Carbonitrile Derivatives

Abstract

Compound 6 is an excellent candidate for a broad spectrum antibiotic with MBCs of 45.6-365.2 μM, while both 3 and 6 have the potential to be developed into an antibiotic against MRSA, with MBCs of 183-199 μM. Since all synthesized compounds showed IC50 values of 10 μM or less especially against the HeLa cells, they can be considered good lead compounds for anticancer agents. Additionally, the docking simulations suggested a good binding affinity of the compounds with Eg5 and indicated their anti-cancer action, at least partially, through its inhibition. The predicted Lipinski descriptors also indicated the potential of these compounds as an orally active drug.

Synthesis of chloro, fluoro, and nitro derivatives of 7‐amino‐5‐aryl‐6‐cyano‐5H‐pyrano pyrimidin‐2,4‐diones using organic catalysts and their antimicrobial and anticancer activities

“…We herein report the synthesis of a small library of chloro, nitro, and fluoro 7‐amino‐5‐aryl‐6‐cyano‐5 H ‐pyrano[2,3‐ d ]pyrimidin‐(1 H ,3 H )‐2,4‐diones using DABCO as a catalyst together with their antibacterial and anticancer activity. This paper follows our earlier report on the synthesis, anticancer, and antibacterial activity of oxygenated pyrimidin‐2,4‐diones …”

“…DABCO was used as an organic catalyst, producing yields of 90% to 96% (Table ). NMR spectroscopy was used to confirm the structures of the compounds, and the structural elucidation was discussed in our previous publication …”

“…We had previously investigated four basic organic catalysts, together with K 2 CO 3 to identify the catalyst among them that produced the greatest yield in the shortest amount of time . We studied L‐proline, dibutylamine (DBA), triethylamine (Et 3 N), and 1,4‐diazabicyclo [2.2.2] octane (DABCO) and found that DBA, Et 3 N, and DABCO all produced yields of over 70% in 1 hour; however, DABCO was the best of the three, resulting in 94% in 38 minutes.…”

“…Upon precipitation, the products were filtered and, thereafter, recrystallized in ethanol before being dried at the vacuum pump. The NMR data of 7‐amino‐5‐phenyl‐6‐cyano‐5 H ‐pyrano[2,3‐ d ]pyrimidin‐(1 H ,3 H )‐2,4‐dione (1) is reported in Aremu et al…”

“…The standard antibiotics ciprofloxacin and ampicillin were used as controls for comparison. The method in Andrews was adapted with modification according to Aremu et al Compounds 2 ‐ 5 , 8 , and 11 showed zones of inhibition >9 mm and their MBC values determined. To calculate the MBC values, the compounds were dissolved in DMSO (4.0 mg mL −1 ) and serially diluted in Mueller‐Hinton broth (Oxoid, England) in Eppendorf tubes.…”