Synthesis and Biological Activities of Some New Phosphorus Compounds Containing Pyranopyrazole Moiety

Abstract

A simple method for construction of functionalized pyranopyrazoles containing phosphoramide and phosphonate groups via one-pot reaction was achieved. The methodology depended on the reaction of 6-amino-3-methyl-1,4-diphenyl-1,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile (3) with triethyl phosphite and hexaethylphosphoramide and so with diethyl phosphite in the presence of chloroacetyl chloride or carbon disulfide. The products were screened for their antimicrobial, antioxidant and antiproliferative properties. Compound 7 displayed promising antimicrobial and antioxidative properties. Also, compound 8 showed potent cytotoxic effects against MCF-7, HepG-2 and HCT-116 cancer cells with IC50 values in range 5.3 ± 0.9 to 7.5 ± 0.6 μg/mL. Acridine orange and ethidium bromide were used for the detection of viable, apoptotic, and necrotic cells. The early apoptotic cell death was observed by the compounds in all types of the treated cells. Compounds 5, 7 and 8 induced high percentage of necrosis towards all treated cells. The late apoptosis was recorded as a high rate after treatment with compound 3 in HepG-2 cells.

Green Synthesis of Pyrazoles: Recent Developments in Aqueous Methods

“…15 Pyrazole containing compounds have various therapeutic and pharmaceutical properties and represent important building blocks for, insectoacaricidal, 16 antibacterial, 17 antidepressant, analgesic, antiviral, anticancer, antioxidant, anti-HIV, COX-2 inhibitor, antiinflammatory, antiproliferative drugs. [18][19][20][21][22][23][24][25][26] Due to multifaceted applications of the pyrazole derivatives, a quite good number of methods for the attainment of the heterocycle have been developed using Al2O3/clay (montmorillonite K10 31 , Amberlyst-70 32 , polymer bound PTSA 33 , silica-supported sulphuric acid (H2SO4•SiO2) 34 , Sc(OTf)3 35 , sulphamic acid 36 as catalysts. Various environmentally benign protocols using green solvent have also been reported in the literature including the synthetic methods using water as solvent.…”

Synthesis of Phosphorus(V)-Substituted Six-Membered N-Heterocycles: Recent Progress and Challenges

“…Moreover, phosphorus(V)-substituted heterocycles exhibit a wide range of biological activities. In particular, pyridines were used to design anticancer [ 6 , 7 , 8 ], antidiabetic [ 9 ], and lusitropic agents [ 10 ], antioxidants [ 11 ], human glucokinase activators [ 12 ], NMDA receptor antagonists [ 13 ], and metalloprotein ligands [ 14 ]. Phosphorus-modified pyridazines are promising candidates as antimicrobial agents [ 15 ] and foliar herbicides [ 16 ].…”