Synthesis and in vitro antimicrobial, antioxidant, and antiproliferative activities of some new pyrano[2,3-c]pyrazoles containing 1,2-azaphospholes, 1,3,2-diazaphosphinines and phosphonate moieties

Abstract

New 1,2-azaphosphole, 1,3,2-diazaphosphinine, and phosphonate derivatives containing pyrano[2,3-c]pyrazole moiety were achieved. The synthetic pathways depended on the reaction of 6-amino-3-methyl-1,4-diphenyl-1,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile with some phosphorus reagents such as diethyl phosphite, phosphorus sulfides, and phenyl phosphorus halides under different conditions. Compounds 6 and 7 recorded potent antibacterial and antifungal activities with lower toxicity, while compounds 4 and 6 displayed promising antioxidative properties. Further, compounds 4 and 9 exhibited potent cytotoxic effects against MCF-7, HepG-2, and HCT-116 cancer cells. The early apoptotic cell death was observed by the compounds in all types of the treated cells. Compounds 3, 5, 7, 10, and 14 recorded low to moderate percentages of necrosis and late apoptosis toward all treated cells.

Graphical Abstract

Keywords:

• Antimicrobial
• antioxidant
• antiproliferative
• 1,2-azaphosphole
• 1,3,2-diazaphosphinines
• phosphonate

Additional information

Funding

The authors extend their appreciation to the deanship of scientific research at King Khalid University for funding this work through research groups program under grant number (RGP.2/2/42).