Nitro Derivatives of Naturally Occurringβ-Asarone and Their Anticancer Activity

[摘要] β-Asarone (2, 4, 5-trimethoxy-(Z)-1-propenylbenzene) was obtained fromAcorus calamus.Nitration ofβ-asarone with AgNO2/I2in ether yielded 1-(2, 4, 5-trimethoxy phenyl)-2-nitropropene (1) but with NaNO2/I2in ethylene glycol obtained 1-(2, 4, 5-trimethoxy phenyl)-1-nitropropene (2). Compound2was 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, compounds1and2have been assignedEconfiguration. Compounds1and2were 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) compound2exhibited five- to tenfold increase in activity compared toβ-asarone and twofold increase over compound1.

[学科分类] 药学