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International Journal of Medicinal Chemistry
Volume 2014 (2014), Article ID 835485, 5 pages
Research Article

Nitro Derivatives of Naturally Occurring β-Asarone and Their Anticancer Activity

1Chemical Sciences Division, Vittal Mallya Scientific Research Foundation, BTM II Stage, Bangalore 560076, India
2Department of Biological Sciences, Vittal Mallya Scientific Research Foundation, BTM II Stage, Bangalore 560076, India

Received 21 July 2014; Accepted 15 September 2014; Published 1 October 2014

Academic Editor: Jochen Lehmann

Copyright © 2014 Suvarna Shenvi et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.


β-Asarone (2, 4, 5-trimethoxy-(Z)-1-propenylbenzene) was obtained from Acorus calamus. Nitration of β-asarone with AgNO2/I2 in ether yielded 1-(2, 4, 5-trimethoxy phenyl)-2-nitropropene (1) but with NaNO2/I2 in 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.