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WANG Xiao-hua, WANG Wei, LIU Chao-mei. Synthesis and antitumor activities of 5-hydroxy-4'-nitro-7-substituted benzyloxy-isoflavone[J]. Journal of Pharmaceutical Practice and Service, 2012, 30(6): 427-429. doi: 10.3969/j.issn.1006-0111.2012.06.008
Citation: WANG Xiao-hua, WANG Wei, LIU Chao-mei. Synthesis and antitumor activities of 5-hydroxy-4'-nitro-7-substituted benzyloxy-isoflavone[J]. Journal of Pharmaceutical Practice and Service, 2012, 30(6): 427-429. doi: 10.3969/j.issn.1006-0111.2012.06.008

Synthesis and antitumor activities of 5-hydroxy-4'-nitro-7-substituted benzyloxy-isoflavone

doi: 10.3969/j.issn.1006-0111.2012.06.008
  • Received Date: 2012-04-22
  • Rev Recd Date: 2012-07-23
  • Objective To design and synthesize genistein's derivatives:5-hydroxy-4'-nitro-7 -substituted benzyloxo-isoflavones and evaluate the antitumor effects in vitro. Methods Benzyl chloride was used as the starting reagent, to obtain title compounds by multi-step reaction:substitution, nitration, Friedel-Crafts reaction, cyclation reaction and benzylation. Results Two important intermediates:4'-nitrodeoxybenzoin and 4'-nitrogenistein and seven title compounds were synthesized, which had been identified by elemental analysis and 1H NMR. Conclusion Introduction of simple substituted benzyl group to 7-posion hydroxy could not enhance the antitumor effects of this type of compounds.
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    [3] Luo LJ, Liu F, Lin ZK, et al. Genistein regulates the IL-1 beta induced activation of MAPKs in human periodontal ligament cells through G protein-coupled receptor 30[J]. Arch Biochem Biophys,2012, 522(1):9.
    [4] Cushman M, Zhu HL, Geahlen RL,et al. Synthesis and biochemical evaluation of a series of aminoflavoens as potential in hibitors of protein-tyrosine kinase p56lck, EGFr, and p60v-src[J]. J Med Chem, 1994,37(20):3353.
    [5] Cushman M, Nagarathnam D, Burg DL,et al. Synthesis and protein-tyrosine kinase inhibitory activities of flavonoid analogues[J]. J Med Chem,1991,34(2):798.
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    [9] 金永生, 刘超美, 吴秋业,等. 新型金雀异黄素衍生物, 5-羟基-4'-硝基-7-取代酰氧基异黄酮的合成及抗肿瘤活性研究[J]. 第二军医大学学报,2005, 26(2):182.
    [10] 金永生, 刘超美, 姚 斌,等. 金雀异黄素类似物的合成及抗肿瘤活性研究[J]. 中国医药工业杂志, 2008, 39(2):85.
    [11] 金永生, 刘超美, 戴 阳,等. 金雀异黄素衍生物,5-羟基-4'-硝基-7-取代酰氧基异黄酮的合成及抗肿瘤活性研究[J]. 第二军医大学学报, 2004, 25(1):111.
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Synthesis and antitumor activities of 5-hydroxy-4'-nitro-7-substituted benzyloxy-isoflavone

doi: 10.3969/j.issn.1006-0111.2012.06.008

Abstract: Objective To design and synthesize genistein's derivatives:5-hydroxy-4'-nitro-7 -substituted benzyloxo-isoflavones and evaluate the antitumor effects in vitro. Methods Benzyl chloride was used as the starting reagent, to obtain title compounds by multi-step reaction:substitution, nitration, Friedel-Crafts reaction, cyclation reaction and benzylation. Results Two important intermediates:4'-nitrodeoxybenzoin and 4'-nitrogenistein and seven title compounds were synthesized, which had been identified by elemental analysis and 1H NMR. Conclusion Introduction of simple substituted benzyl group to 7-posion hydroxy could not enhance the antitumor effects of this type of compounds.

WANG Xiao-hua, WANG Wei, LIU Chao-mei. Synthesis and antitumor activities of 5-hydroxy-4'-nitro-7-substituted benzyloxy-isoflavone[J]. Journal of Pharmaceutical Practice and Service, 2012, 30(6): 427-429. doi: 10.3969/j.issn.1006-0111.2012.06.008
Citation: WANG Xiao-hua, WANG Wei, LIU Chao-mei. Synthesis and antitumor activities of 5-hydroxy-4'-nitro-7-substituted benzyloxy-isoflavone[J]. Journal of Pharmaceutical Practice and Service, 2012, 30(6): 427-429. doi: 10.3969/j.issn.1006-0111.2012.06.008
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