Nitro derivatives of naturally occurring β -asarone and their anticancer activity

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Abstract

β-Asarone (2, 4, 5-trimethoxy-(Z)-1-propenylbenzene) was obtained from Acorus calamus. Nitration of β-asarone with AgNOIin ether yielded 1-(2, 4, 5-trimethoxy phenyl)-2-nitropropene (1) but with NaNOIin ethylene glycol obtained 1-(2, 4, 5-trimethoxy phenyl)-1-nitropropene (2). Compound 2 was prepared for the first time and characterized using IR, 1H-NMR, 13C-NMR, and GC-MS spectra and it was converted into 1-(2, 4, 5-trimethoxy) phenyl-1-propanone (3) using modified Nef reaction. Based on 1D NOESY experiments, compounds 1 and 2 have been assigned E configuration. Compounds 1 and 2 were subjected to cytotoxic activity using five human cancer cell lines, namely, MCF-7, SW-982, HeLa, PC-3, and IMR-32 by MTT assay. Except in breast cancer line (MCF-7) compound 2 exhibited five- to tenfold increase in activity compared to β-asarone and twofold increase over compound 1.

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Shenvi, S., Diwakar, L., & Reddy, G. C. (2014). Nitro derivatives of naturally occurring β -asarone and their anticancer activity. International Journal of Medicinal Chemistry, 2014. https://doi.org/10.1155/2014/835485

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