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

International Journal of Medicinal Chemistry Pub Date : 2014-01-01 Epub Date: 2014-10-01 DOI:10.1155/2014/835485
Suvarna Shenvi, Latha Diwakar, G Chandrasekara Reddy
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引用次数: 8

Abstract

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, (1)H-NMR, (13)C-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.

Abstract Image

天然β -细辛酮的硝基衍生物及其抗癌活性
从菖蒲中分离得到β-细辛酮(2,4,5 -三甲氧基-(Z)-1-丙烯苯)。用AgNO2/I2在醚中硝化得到1-(2,4,5 -三甲氧基苯基)-2-硝基丙烯(1),用NaNO2/I2在乙二醇中硝化得到1-(2,4,5 -三甲氧基苯基)-1-硝基丙烯(2)。首次合成了化合物2,并利用IR、(1)H-NMR、(13)C-NMR和GC-MS谱对其进行了表征,并利用修饰的Nef反应将其转化为1-(2,4,5 -三甲氧基)苯基-1-丙烯(3)。基于1D NOESY实验,化合物1和2被分配为E构型。化合物1和2采用MTT法对MCF-7、SW-982、HeLa、PC-3和IMR-32等5种人癌细胞进行细胞毒活性研究。除乳腺癌细胞系(MCF-7)外,化合物2的活性比β-细辛酮高5 - 10倍,比化合物1高2倍。
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期刊介绍: International Journal of Medicinal Chemistry is a peer-reviewed, Open Access journal that publishes original research articles as well as review articles in all areas of chemistry associated with drug discovery, design, and synthesis. International Journal of Medicinal Chemistry is a peer-reviewed, Open Access journal that publishes original research articles as well as review articles in all areas of chemistry associated with drug discovery, design, and synthesis.
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