Sn(Ii)-Mediated Facile Approach for the Synthesis of 2-Aryl-2h-indazole-3-phosphonates and Their Anticancer Activities
New journal of chemistry(2017)
摘要
A convenient three-component method was developed for the synthesis of various 2-aryl-2H-indazole-3-phosphonates using SnCl2·2H2O under conventional heating techniques. The transition metal free reaction, mild reaction conditions, one-pot operation, open flask conditions, wide substrate scope and good yields are a few important features of this methodology. This protocol proceeds with high atom economy via the formation of α-aminophosphonates followed by the generation of an indazole ring through N–N bond formation, eliminating water as a by-product. The cytotoxic properties of the 2-aryl-2H-indazole-3-phosphonate derivatives were investigated against A549 and HepG-2 cells. Interestingly, compounds 4d and 4g showed potent cytotoxic properties against HepG-2 cells and compound 4p showed significant cytotoxic properties against A549 cells. Intracellular visualization was done using a laser scanning confocal microscope. DNA fragmentation, colony formation, and apoptosis studies, flow cytometry and western blot analysis for 4p against A549 cells have also been reported.
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