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Issue 13, 2017
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Sn(II)-Mediated facile approach for the synthesis of 2-aryl-2H-indazole-3-phosphonates and their anticancer activities

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Abstract

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.

Graphical abstract: Sn(ii)-Mediated facile approach for the synthesis of 2-aryl-2H-indazole-3-phosphonates and their anticancer activities

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Publication details

The article was received on 14 Mar 2017, accepted on 15 May 2017 and first published on 15 May 2017


Article type: Paper
DOI: 10.1039/C7NJ00843K
Citation: New J. Chem., 2017,41, 5582-5594
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    Sn(II)-Mediated facile approach for the synthesis of 2-aryl-2H-indazole-3-phosphonates and their anticancer activities

    N. Sudhapriya, C. Balachandran, S. Awale and P. T. Perumal, New J. Chem., 2017, 41, 5582
    DOI: 10.1039/C7NJ00843K

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