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Issue 41, 2016, Issue in Progress
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Cathepsin B, H and L inhibitors as cell proliferating agents: design, synthesis, computational and pharmacological studies of some novel 2-(2-naphthoyl)-6,6-dimethyl-3-aryl-2,3,6,7-tetrahydrobenzofuran-4(5H)-ones

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Abstract

Elevated levels of cathepsins B, H and L in disease conditions such as inflammation and cancer accentuate the need for design, synthesis and pharmacological evaluation of new compounds, keeping in view target-specific therapy. The present work describes the one pot multicomponent synthesis of some novel 2-(2-naphthoyl)-6,6-dimethyl-3-aryl-2,3,6,7-tetrahydrobenzofuran-4(5H)-ones in good yields. The synthesized compounds were analysed by spectral and X-crystallographic studies and have been found to be potential inhibitors to cathepsins B, H and L. The extent of inhibition varied with the substitution. Among the synthesized compounds, nitro-substituted compound 1d has been evaluated as most inhibitory to cathepsin H, however fluoro-substituted compound 1f was the best inhibitor of cathepsin B and cathepsin L. The compounds have been found more selective towards cathepsin L. In vitro inhibition studies correlate well when tested using MTT assay on HepG2 cells, a hepatocellular carcinoma cell line. The results validated by in silico studies performed with iGemDock predicted that among the synthesized compounds, 1d experiences the highest affinity for cathepsin B and H sites, whereas 1f has the highest affinity to cathepsin L.

Graphical abstract: Cathepsin B, H and L inhibitors as cell proliferating agents: design, synthesis, computational and pharmacological studies of some novel 2-(2-naphthoyl)-6,6-dimethyl-3-aryl-2,3,6,7-tetrahydrobenzofuran-4(5H)-ones

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Publication details

The article was received on 11 Mar 2016, accepted on 17 Mar 2016 and first published on 30 Mar 2016


Article type: Paper
DOI: 10.1039/C6RA06480A
RSC Adv., 2016,6, 34588-34599

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    Cathepsin B, H and L inhibitors as cell proliferating agents: design, synthesis, computational and pharmacological studies of some novel 2-(2-naphthoyl)-6,6-dimethyl-3-aryl-2,3,6,7-tetrahydrobenzofuran-4(5H)-ones

    N. Raghav, S. Jangra, A. Kumar, S. Bhattacharyya, D. Wadhwa and J. Sindhu, RSC Adv., 2016, 6, 34588
    DOI: 10.1039/C6RA06480A

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