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

WANG Xiao-hua; WANG Wei; LIU Chao-mei

doi:10.3969/j.issn.1006-0111.2012.06.008

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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.

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

1. The 202nd Hospital of PLA, Shenyang, 110003, China

2. The 455th Hospital of PLA, Shanghai, 200052, China

3. Department of Organic Chemistry, School of Pharmacy, Second Military Medical University, Shanghai 200433, China

Received Date: 2012-04-22

Rev Recd Date: 2012-07-23

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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.

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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

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